Since permanent settlement began on this peninsula in Casco Bay the town has answered to many names: Casco, Falmouth and Portland among them. It has also put on many faces. There was a rebuilding of 75% of the town after British Captain Henry Mowatt cannonballed the lumber port to the ground in the early days of the Revolutionary War.

And there was the recovery from the Embargo Act of 1807 that closed the thriving port. The town of 8,000 people was barely staggering back on its economic feet when it was named the capital of the new state of Maine in 1820. The government sashayed out of town to safer inland quarters a dozen years later but Portlanders paid no mind. The largest fleet on the East Coast was anchored here and railroads were coming to link the commercial wharves to Canada and points West. Landfill created Commercial Street on the waterfront in the early 1850s and it rapidly filled with prosperous shipping and mercantile concerns.

And there was the Great Fire of 1866 that broke out on Independence Day, maybe from some careless handling of fireworks. More than 10,000 people were left homeless - it was the worst urban fire in American history to that point. It sounds bad but only two lives were lost and the city rebuilt with startling alacrity. Scores of brick buildings emerged in the downtown area, many of high Victorian style by talented architects. The Old Port remains a thick tapestry of brick commercial buildings to this day. 

Portland became an active player in urban renewal in the 1960s. Several beloved landmarks were lost: the Falmouth Hotel that was the city’s leading guest house of the 19th century, the grand Richardsonian Romanesque-styled Union Station, the Grand Trunk Railroad Station, the old post office. Things were getting so out of hand that Greater Portland Landmarks was hastily started in 1964 to stem the tide.

We will set out to see what was saved from a small park on Congress Street, which transformed after the Great Fire from a residential to commercial showplace, stuffed with fine hotels and department stores which had the goods of the world on offer. Enough remains that the American Planning Association named Congress Street one of America’s Top 10 great streets in 2014... 

Lincoln Park
bounded by Congress Street, Franklin Street, Federal Street and Pearl Street

Before there was a Great Chicago Fire in 1871 there was the 1866 Great Fire of Portland. It was Independence Day and maybe it was a firecracker that started a fire in a boat house on Commercial Street. A lumber yard quickly went up in flames and soon Portland was experiencing the worst fire an American city had ever seen. Some 1,800 buildings perished in the conflagration. Although only two people died, about 10,000 were without homes that night. It was a doubly solemn occasion when this park at just about the geographic center of the city was dedicated after the fire and named for Abraham Lincoln who had just been assassinated the year before.


Portland Central Fire Station
380 Congress Street at southeast corner of Pearl Street

The Portland Fire Department traces its roots back to 1768 when seven “wardens” were tasked with watching for fires at night to alert residents. In 1787 a pumper from England arrived to be the town’s first piece of firefighting apparatus. This two-story building with space for administrative work and six engine bays went into operation on November 10, 1924. Local architects William R. Miller and Raymond J. Mayo infused the lively design with Spanish Colonial and Pueblo Revival elements (note the concrete “vigas” protruding from the arched central window hoods). The price tag was $86,918. The fireman statue at the corner, fashioned from granite, was dedicated in 1892 and moved to its current post in 1987.

GannettBuilding/Press Herald Building
390 Congress Street at southeast corner of Market Street

William H. Gannett began publishing Comfort magazine in 1888 in Augusta and it became one of the first magazines to boast a circulation north of one million. Guy Gannett, a Yale graduate, helped his father out at the Comfort and dabbled in local politics. In 1920 he was asked to invest in two struggling daily papers: the Portland Herald and the Portland Daily Press, which had been covering the news since 1862. He owned them outright by 1921 and merged the operation into the Portland Press Herald. Shortly thereafter he added the Evening Express and Daily Advertiser and Portland Sunday Telegram to his stable of local papers. George Henri Desmond, a Boston-based architec, drew up the plans for Gannett’s base of operations in the rear in 1924. The seven-story Classical Revival structure to the rear is rendered in limestone ashlar and buff brick.

Gannett segued into radio with WGAN in 1938 and became engaged with the Rines department store family to put the first Portland television station on the air. Rines and WCSH won the race but operated in converted quarters in the Congress Square Hotel. WGAN actually created the first purposely built television studio in Maine in the front half of the block; the building was raised in 1947. Look up to see a windowless fifth floor - that was the original WGAN studios.

Portland City Hall
389 Congress Street

Portland’s first city hall on this site rose in 1862 but was wiped out in the 1866 fire. Next up was a grand block-swallowing government fortress capped by an octagonal dome, designed by local architect Francis H. Fassett. Unfortunately in 1908 a fire destroyed the monumental government home. Ironically, the fire is believed to have ignited from faulty electrical wires in the alarm room and the fire department - right across the street - did not discover there was a blaze in progress until it was too late. The current government seat came from the drawing boards of Carrère and Hastings in New York City, one of the most celebrated Beaux Arts architectural firms of the early 20th century. This was one of Brazilian-born John Merven Carrère’s last creations before he died at the age of 52 in 1911 and he is reported to have said, “he would rather have his reputation rest on the Portland City Hall than upon any other building he designed.” Quite a declaration considering his works included the New York Public Library, the Manhattan Bridge and both the Russell Senate Office Building and the Cannon House Office Building on Capitol Hill in Washington, D.C. Carrère created a U-shaped structure with the wings covered by hip roofs and a four-story central block under a 200-foot tower. A public auditorium resided in City Hall that could accommodate 3,000 people and featured the second largest organ in the world, donated by Portland native and publisher of the Ladies Home Journal and  Saturday Evening Post, Cyrus Hermann Kotzschmar Curtis. Curtis was forced to drop out of high school due to the Great Fire in 1866 and ended up by inflated-adjusted accounts as one of the 100 richest people who ever  lived. Maine granite from North Jay was used in the construction of one of America’s finest city hall buildings. 

Union Mutual Building
396 Congress Street at southeast corner of Exchange Street

By the 1920s large, showy French Second Empire-styled commercial buildings were as out of date as horse-and-buggies. The Boston architectural firm of Hutchins & French rectified that situation for the Union Mutual Insurance Company and Portland National Bank in 1929 by lopping the mansard roof off the 47-year old block that stood here and providing a crisp Colonial Revival exterior. Unlike textbook Colonial Revival designs this one is not symmetrical as marked by the Corinthian pilasters; the architects retained the openings of the Victorian original.
Post Office Square
400 Congress Street at northeast corner of Temple Street

This sleek brick and polished granite ornament with bands of glass windows and a rounded corner was the Art Moderne creation of Philip Shirley Wadsworth and Royal Boston, Jr. who teamed up in 1930. This building was constructed in 1956; the firm operated until 1990.

Masonic Block
415 Congress Street

Frederick A. Tompson started work in the office of Francis H. Fassett, Maine’s most prominent Victorian architect, at the age of 19 in 1876. Within ten years he worked his way up to partner before hanging out his own shingle in 1891. For the final 28 years of his life Tompson was responsible for many signature Portland buildings including the George C. West House, the city’s largest private residence, in the West End and this home for the Grand Lodge of Maine. Both designs were executed in 1911. The Beaux Arts temple was for business and pleasure for the city’s Masons, who were first chartered in 1796 with Paul Revere among the founding members. There were nearly 21,000 Masons in Maine when the hall, infested with Masonic Order symbols in its design, was constructed.

First Parish Church
425 Congress Street

The congregation first gathered in 1674 and began regular services in a log church in 1718. In 1740 a frame house of worship rose on this site which was replaced by this granite ashlar church in 1826. Stone churches were rare sights indeed in New England at that time and this one, using undressed Rockport granite, was the first built in Maine; today, after surviving the 1866 fire, it is the oldest house of worship in Portland. The graceful Federal style provided by congregant John Mussey is best observed in the multi-stage clock tower with octagonal wooden cupola and wooden spire. 

Metropolitan Building
431-443 Congress Street

Here is another example of 1920s updating, decades removed from the Victorian age. Renovators descended upon the 50-year old Farrington Block in 1926 and stripped the commercial block of its Italianate ornamentation and replaced the facade with a sparse Classical Revival vibe, leaving most of the decoration for the recessed main entrance. It also got a new, big-sounding 20th century name: The Metropolitan. 

Clapp Memorial Building
443-449 Congress Street at northwest corner of Elm Street

This Classical Revival commercial block is an original, built in 1924 to replace the home of sea captain Asa Gabriel Clapp. Clapp was born on an East Mansfield, Massachusetts farm in 1762 and before he turned 21 years of age he had fought against the British in the Revolution and taken command of his own privateering ship. He dropped anchor for the last time in 1795 and became a full-time resident of Portland, reaping the profits of his merchant fleet until his death in 1848. His descendants sacrificed his Federal-style mansion for this seven-story commercial block, designed by Jules Henri de Sibour, a French architect based in Washington, D.C. De Sibour was known for applying his classical sensibilities to embassy buildings around the nation’s capital. The Clapp family kept possession of the property until 2011. 

Portland Public Library
5 Monument Way

Portland had a subscription library in 1826 and the Portland Athenaeum built its collection to more than 10,000 volumes before losing it all in the 1866 fire. A decade later the Athenaeum merged with the Portland Institute to create a free lending library. Portland began borrowing its books at this location in 1979; the building is said to be the last major project completed in the International Style in the United States.

Monument Square

The namesake monument is the Portland Soldiers and Sailors Monument, dedicated in 1891 to the Portland’s Civil War dead. Franklin Simmons, a native of Webster, Maine, who contributed several sculptures to the United States Capitol and the National Statuary Hall Collection, created the bronze statue of “Our Lady of Victories” and Richard Morris Hunt, one of the 19th century’s pre-eminent architects, designed the granite base. Francis H. Fassett handled the landscaping, which has been much changed in the hundred-plus years since. The local Grand Army of the Republic lodge picked up the bill for all that creative firepower. 


Commercial Block
15-22 Monument Square

The four picturesque commercial buildings here form one of Portland’s most attractive streetscapes. The Choate Block to the far left at #15 is a product of the Francis H. Fassett and Frederick Tompson partnership, a Romanesque-styled four-story block fashioned from buff brick in 1891. John Calvin Stevens was another architect who trained in the Portland office of Fassett. He opened his own office in 1884 and went on to design more than 1,000 buildings in Maine, including the two in the middle here. At #18 he crafted a one-bay structure in 1913, relying on intricate brickwork for ornamentation. In the same year he expanded #22 from two stories to six, decorating the brick piers with classical flourishes of white terra cotta. The Emerson Clapp Building at #28 is an 1870s survivor, built by the Clapp family back when they could still keep an eye on their commercial property from their mansion across the square. The facade dates to a 1909 makeover.

Fidelity Trust Company
467 Congress Street

G. Henri Desmond gave Portland its first skyscraper in 1909. The Boston architect hewed to the convention of designing early high-rises in the form of a classical column with a defined base (the oversized ground level), a shaft (the unadorned center stories) and a capital (the ornate decorations applied to the upper story. Desmond used high quality Indiana limestone and infused the facade with Gothic-inspired classical ornamentation. When finished the 130-foot tower was not only the tallest building in Maine but the tallest north of Boston. Desmond’s client was Charles Sumner Cook, a Portland native who began his working career as a high school principle before being admitted to the Cumberland County bar in 1886. He organized the Fidelity Trust Company in 1906 and served successively as vice-president, president and chairman of the board.

Lancaster Block
474 Congress Street

This handsome six-story commercial block was erected in 1881, the handiwork of Francis Fassett and John Calvin Stevens. The moneyman was John B. Brown, who could afford to hire Portland’s best designers. How rich was John Bundy Brown, Maine’s richest man and Portland’s largest landholder? He lost 17 properties in the Great Fire of 1866 reported to be worth half a million dollars (in mid-19th century money when a good wage was a dollar a day) and many years later a member of the Brown family recalled, “I did not get a sense this was a big event in our family.” Brown started his business career as a grocer in 1828 when he was 20 years old. In 1840 he founded the Portland Sugar House which became the basis for the state’s greatest 19th century business empire. Most of Brown’s money went into real estate and he was responsible for developing much of Congress Street. Brown had built one of his first buildings on this spot thirty years earlier. Like this block it was named after his birthplace in Lancaster, New Hampshire.  

Time and Temperature Building
475 Congress Street

The second of Portland’s twin towers rose in 1924 on plans drawn by local architect Herbert W. Rhodes. The building extends out the back down Preble Street to the city’s vaudeville house, the B.F. Keith Theater. The shops that passed along the way were called The Arcade, and represented the city’s first indoor shopping mall. The Classical Revival, 14-story tower was originally known as the Chapman Building but became known as the Time and Temperature Building because of a flashing screen on the roof that tells Portland the time and temperature.

Preble House
481 Congress Street

Portland native Edward Preble was one of the legendary early United States Navy Commodores with commands of the USS Pickering, USS Essex and USS Constitution. Poor health forced his return to Portland where he oversaw construction of a stately Federal style house on this corner in 1806. He never got a chance to live in the house as he died from intestinal disorders at the age of 46 the following year. It was said the Preble House was the first building in Maine to be heated with a furnace instead of a fireplace. Mrs. Preble lived until 1851 after which the mansion became the guts of the second largest hotel in the city with 150 rooms. Most of the hotel was razed to make room for the adjoining tower but this section was retained and the ground level altered to mesh stylistically with the Chapman Building.

Wadsworth-Longfellow House
489 Congress Street

Holding its plot against nearly 250 years of development is Portland’s oldest surviving house. Brigadier General Peleg Wadsworth returned from the Revolutionary War to buy 1.5 acres along Congress Street and build the first all-brick house in town. The Wadsworths raised ten children here and then grandson Henry Wadsworth Longfellow spent years one through 36 in the house. The poet and educator’s birth house was demolished in 1955 but the Maine Historical Society has held sway here since the last family member died in 1901, making it only the second American author’s home to be preserved and opened to the public.

Beaver Block
496 Congress Street at northeast corner of Brown Street

This Queen Anne commercial block was added to the Congress streetscape in 1885 by Francis H. Fassett. The name stamp is front and center in red terra cotta. Briceno M. Eastman Ermon D. Eastman and Fred E. Eastman opened a dry goods store on this corner in 1865 and their mercantile operation moved into this building and the one next door. Eastman Brothers & Bancroft shuttered during the Great Depression and sold the building to Filene’s Department Stores n 1937.

Owen, Moore & Company
504 Congress Street

This splash of Streamlined Moderne styling took its cues from the curves in airplanes and automobiles in the 1940s. The original store, Owen Moore’s, was a place to pick up fine clothes and headwear. George Cushman Owen and George M. Moore organized the business in 1874.

W.T. Grant Store
510 Congress Street

William Thomas Grant was 30 years old when he opened his first “W. T. Grant Co. 25 Cent Store” in Lynn, Massachusetts in 1906, using $1,000 he had saved up from working as a salesman. Portland picked up its Grant’s dime store in 1942, in a Colonial Revival building designed by Boston architects Joseph Daniels Leland and Niels Hjalmar Larsen. At the time the large pediment boasted a model of the Dash, a privateer built in Freeport that took 15 prizes under four captains in the War of 1812 without the loss of a single crewman. She and a crew of 60 were lost in 1815 during a heavy winter gale.

Mechanics Hall
519 Congress Street at northwest corner of Casco Street

The Maine Charitable Mechanical Association organized in 1815 to promote the livelihood of those engaged in the “mechanical arts.” One of the members was Thomas P. Sparrow, considered Portland’s first native architect of distinction. Sparrow designed this granite hall in the Italianate style in 1857; only three Sparrow creations are known to exist and this is the best. The heritage landmark sports window quoins and a bracketed cornice. Mechanics Hall is still owned by the 200-year old organization and it is still sponsoring lectures and maintaining its library.

Miller Building
522-528 Congress Street

William Miller had started in the dry goods business in Portland in 1897 with partner James W. Watson, a teaming which soon expired. Miller dreamed of opening an elegant department store in the center of the Portland business district that he was going to call the Boston Store since it would carry only the finest goods. Penn Varney, an architect from Lynn, Massachusetts, provided the Renaissance Revival design to do the job for the Miller Building that opened in 1904. Within two years, however, Miller was out of the retail game and a Connecticut department store chain operated by John Porteous, John B. Porteous, Archibald Mitchell, and Robert Braun were at the helm. Porteus, Mitchell and Braun would be the city’s leading department store for most of the remainder of the century. Local architect George W. Burnham was called upon to expand the property in 1911 while preserving the classical terra cotta styling. More expansions eventually filled the entire depth of the block. The department store survived until 1991 and the building is now the home of the University of Maine College of Art.

Brown Memorial Block
537 Congress Street at southwest corner of Casco Street

John Bundy Brown was 19th century Portland’s greatest builder so to honor his legacy after his death at the age of 76 in 1881 his family could think of no greater memorial than to raise one of the city’s grandest structures. John Calvin Stevens tapped the picturesque Queen Anne style to create the five-story Congress Street showcase, executed in red brick and red terra cotta. The massing is asymmetrical and the roofline is irregular with three different sizes of gables and protruding chimneys. Carved terra cotta spandrels accent the windows of the facade. A curved vertical course of bricks lead the way to J.B. Brown’s signature, immortalized in granite in the center of the building.

FW Woolworth’s
542 Congress Street

Although the ground level has been compromised you can still look up and see the Art Deco form of this two-story, seven-bay commercial block. The upper floor windows boast Byzantine and Moorish designs, popular themes mined by Deco practitioners, in this case Clevendon, Varney & Pike of Boston. The building began life on November 7, 1946 as a branch of the F.W. Woolworth chain.

Brown Block
549 Congress Street

Charles A. Alexander was one of John Bundy Brown’s favorite architects who built the sugar baron’s Italian villa, Bramhall, on the Western Promenade in 1855. He borrowed elements of the same style for this commercial block a decade later. It was originally three stories with a mansard roof but received a sympathetic expansion many years later. 

Dreamland Theater
551 Congress Street at northwest corner of Oak Street

There is not much here to rekindle memories of Dreamland, the first building constructed in New England solely to exhibit motion pictures; it opened here in 1907. That building featured a festive arched entrance under a Flemish stepped gable. It received a Spanish-flavored Art Deco makeover in 1929 with buff-colored terra cotta which is still visible.

Baxter Memorial Building
562 Congress Street

James Phinney Baxter was born in Gorham, Maine in 1831 but lived in Portland for over 80 years beginning at the age of nine. Baxter was pointed towards a career in law in Boston before ill health returned him to Maine. Baxter and William G. Davis started a dry goods firm that became the Portland Packing Company in 1862, Maine’s largest vegetable canning business. Portland Packing grew to include 13 factories in the state as Baxter spread his business interests to include banking, ferries and the Maine Central Railroad. He passed his company on to his sons in the 1880s and devoted himself to historical research (30 years as the president of the Maine Historical Society and editor of 20 volumes of The Documentary History of Maine), fishing and the outdoors (Baxter State Park, home of the state highpoint at Mount Katahdin, is named for him), and philanthropy. He commissioned this commercial block as a memory of his father, Elihu Baxter, in 1894. Francis H. Fassett delivered one of Portland’s most eclectic and distinctive buildings in an exuberant Queen Anne style. This was the home of department stores, first J.R. Libby & Company and, after 1935, Montgomery Ward. In a 1950s renovation all ornamentation was covered or destroyed and an elaborate two-story corner turret that had been a staple of the Portland skyline for over half a century was pulled down.

Congress Square Hotel
579 Congress Street at southwest corner of Forest Avenue

Travelers could always count on a reliably good meal when they stopped at the New England House after it opened in 1850. It was soon the City Hotel. But after being sold to Henry Rines the four-story guest house was not long for this world. Rines, whose four cousins operated the city’s largest department store in the Brown Memorial Block, hired Francis Fassett to build a new hostelry, the Congress Square Hotel. Fassett went into his classical toolbox and came up with a Romanesque Revival design. In this building Rines started Maine’s first commercial radio station, WCSH, in 1925 and also launched New Hampshire’s first commercial television venture, WFEA. He also created the First Radio Parish Church of America with Reverend Howard O. Hough delivering Daily Devotions. And Maine’s first television transmission emanated from the top floor of the Congress Square Hotel in December of 1943.

Hay Flatiron Building
594 Congress Street at Free and Middle streets

Henry Homer Hay was born in 1820, the son, grandson and great grandson of New England physicians. His family moved to Portland in 1828, just after Charles Quincy Clapp, a self-taught local architect, was putting the finishing touches on this building constructed to conform to the triangular lot - a flatiron building. The structure was two stories at the time and the sunburst patterns on the second floor windows betray its Federalist style origins. Hay began clerking in the drug, paint and dye stuff shop of Masters & Company on Middle Street before establishing H.H. Hay Company in 1841. He moved his apothecary business here in 1856, as he dispensed medicines and flavored syrups for drinks and exported them all over the world until his death in 1895 Edward A. Hay and Charles M. Hay carried on the family trade as H.H. Hay & Sons. John Calvin Stevens added the third floor in 1922.

Eastland Hotel
157 High Street at the northwest corner of High Street

Henry Rines bankrolled the largest hotel (when connected to his Congress Square Hotel) in New England in 1927. Rines and his wife Adeline (the first woman to practice law in Cumberland County) were seasoned travelers to Europe and the Middle East and they advised on such cosmopolitan touches as the Egyptian dining room, the Danish Tea Room and the Spanish-flavored entrance. Ever the promoter, Rines staged a name-the-hotel contest and gave Portlander C.E. Weeks $100 in gold for his entry, Eastland. In a grand gesture at opening, one of Rines’ radio personalities, Graham McNamee, flew over Portland Harbor and dropped the keys to the hotel’s front door into the water, announcing to all of Portland that the Eastland would never close. The final bill was $2 million. Rines died in 1939 so it is not known what he would have thought of subsequent publicity generated at his dream hotel. In 1946 the management refused to allow Eleanor Roosevelt to stay in the Eastland with her dog and years later rocker Ozzy Osbourne was escorted out of town by police after hosting a party that included throwing pool furniture off the roof and into the street. The Eastland was forced to close the hotel pool after guests kept honoring Ozzy by engaging in furniture tossing as well. 

State Theatre/Congress Building
615 Congress Street

The State Theatre opened on November 8, 1929, one week after the collapse of Wall Street. It was the heyday of atmospheric movie palaces designed to transport patrons on exotic escapist journeys of the mind. Portland architect Herbert W. Rhodes provided the State with a Spanish motif, including a quartet of Castilian balconies in the 2,300-seat screening room. The interior abounded with wrought iron stairs, bronze trim and tapestry rugs descending from vaulted ceilings. The State followed a familiar arc for downtown movie houses in America - several decades of bountiful prosperity and then a quick decline in the age of television and suburban flight, finally spending its final days as an exhibitor of adult movies. Unlike most of its brethren the State received new life, first in a brief revival in the 1990s and, most recently, as a performing arts venue in 2010. 

Baxter Library
619 Congress Street

Architect Frank Fassett, armed with James Phinney Baxter’s money, gave Portland this landmark street ornament in 1888. The Portland Packing Company magnate was already at the forefront of civic improvement in the city having served six terms as mayor and leading an expansion of Portland’s city parks. The library would check out books for 90 years. Fassett borrowed elements of Henry Hobson Richardson’s Romanesque-inspired style for the library including checkerboards of multi-colored stone, a prominent front-facing gable, polished pillars for round-head windows and a bold arched entryway. Burly Richardsonian Romanesque civic buildings were favorites of the Gilded Age.


Portland Museum of Art
7 Congress Square

The Portland Society of Art was founded in 1882 and now has expanded to three facilities along High Street. The core of Maine’s largest and oldest public art institution was kickstarted by Margaret Jane Mussey Sweat in the early 1900s. The Sweat home was at the corner of High and Spring streets, an 1801 Federal-styled mansion constructed by Major Hugh McLellan, owner of Maine’s largest shipping fleet. He also started the state’s first bank and first insurance company. McLellan spent $20,000 to build Portland’s finest house and had Ipswich, Massachusetts architect John Kimball draw up the plans. A lethal dose of ill fortune saw McLellan lose both his wife to an early death and his shipping empire after President Thomas Jefferson signed the Embargo Act of 1807 and the house was put up for auction. Portland politician and United States Congressman during the Civil War, Lorenzo de Medici Sweat, bought the house in 1880. Mrs. Sweat, a Victorian art lover, bequeathed the property to the Society in 1908 with enough additional funds to construct the L.D.M. Sweat Memorial Galleries, designed by John Calvin Stevens, in 1911. Maine native Charles Shipman Payson, who was married to the co-founder and majority owner of the New York Mets, Joan Payson, made future expansion possible in the 1980s with an $8 million donation to fund the post-modern keystone of the Portland Art Museum, desinged by Henry Nichols Cobb of I.M. Pei & Partners.

Cumberland Club
116 High Street

The Cumberland Club was founded in 1877 “for the purpose of mutual enjoyment of cultural and social amenities.” One of those amenities for Maine’s leading politicians and businessmen was a work-around of Maine’s prohibition of alcohol (it was the first state to ban alcohol sales and was followed by 18 others) which provided possession of booze in a personal collection. So the club was a place for members to “store” their bottles in a private room. The clubhouse is a textbook Federal-style house from the early 1800s, executed in brick.

Safford House
93 High Street at southeast corner of Spring Street

This 1858 townhouse in the Italian Renaissance style has been restored by Greater Portland Landmarks for use as its headquarters.


Clapp House
97 Spring Street

After Hugh McLellan lost his house next door it was lived in for a time by Charles Quincy Clapp. It was a gift in 1820 from his father who was one of the town’s wealthiest businessmen. Charles was a builder able to indulge his passion as a “gentleman architect.” He made some Greek Revival changes to the Federal-style McLellan House but in 1832 he was able to bring his ideas to a more fully realized conclusion with his own house. Fluted Ionic columns and pilasters frame entrance porticos on both sides of the structure and each is accessed by a separate granite stair. The house survived the Great Fire of 1866 and stands as Portland’s best example of high style Greek Revival architecture. 

Cross Insurance Arena
1 Civic Center Square

This multi-purpose arena for sports and concerts came online in 1977. To help pay the $8 million price tag individually engraved seats were sold to local businesses and residents. Portland and the Cross Arena was the next stop on Elvis Presley’s concert tour when he died the day before on August 16, 1977.


Casco Bank Block
193 Middle Street

This Italianate headquarters was raised in 1867, right from the ashes of the Great Fire of 1866. Casco was chartered as one of Maine’s first state banks in 1824 but shareholders had voted after the passage of the National Bank Act in 1865 to turn in its charter and have a go at operating as a national bank, with the right to print its own currency. Almost $2 million is currency and notes burned along with the Casco bank building the following year. Prosperity followed the new banking hall, however, and in 1897 Casco merged with the Mercantile trust Company that brought it to new markets a round Maine. That bank failed during the Great Depression and a new Casco Bank & Trust Company emerged in its place. The bank left these quarters in 1970.

Canal Bank Building
188 Middle Street

The two dates etched into the upper facade give clues to the story of Canal Bank. The 1820s were the golden age of canal building in the United States and in southern Maine the project was to link its largest lakes, Long Lake and Sebago Lake, with the seacoast at Portland. A state lottery raised $50,000 for the Cumberland and Oxford Canal and the Canal Bank of Portland was chartered to manage the funds; it opened for business in this building in 1826. The 28 granite locks necessary to make 38 miles of navigable waters were completed in 1832. The 1930 date is when the bank’s Victorian headquarters was expanded and given a Colonial Revival makeover.

Oxford Building
183-187 Middle Street

Cullen Chapman was the money man for this handsome commercial block. Chapman was born in Bethel, Maine in 1833 and became a dry goods merchant in Portland. He then headed the Chapman Banking Company that he formed with his brothers in 1890. John Calvin Stevens provided the balanced Romanesque Revival design with a center bay window using brownstone, brick and terra cotta. Stevens, one of the leading Victorian architects in Maine, liked it well enough to make his offices in the top floor.

Boyd Block
178 Middle Street at southeast corner of Exchange Street

Architect George M. Harding was Massachusetts born and trained but moved to Northern New England in his twenties to practice. He started in Concord, New Hampshire in 1854 and then moved to Manchester. Harding settled in Portland in 1858 and became one of the city’s busiest designers after the Great Fire of 1866. The exuberant Italianate-styled Boyd Block was one of those post-conflagration efforts. The fifth floor, with only a half-hearted attempt to carry on Harding’s design, was added in 1900.

First National Bank Block
57 Exchange Street at northeast corner of Middle Street

Henry Van Brunt was one of Boston’s most celebrated post-Civil War architects and this is one of his last creations before moving to Kansas City in the mid-1880s to design grand passenger stations for the Union Pacific Railroad. Van Brunt blended several styles for this eclectic composition for the First National Bank - Romanesque Revival windows on the ground floor; a touch of classicism with the keystone windows, brick pilasters and entryway surround; and Queen Anne at the upper floors with an asymmetrical roofline, carved sandstone and terra cotta and corner tower. The tower was even more picturesque at one time, soaring higher with a clock and cupola. A lot going on here.


Widgery Block
36-40 Exchange Street

William Widgery Thomas was a seventh generation direct descendant of Portland founder George Cleeves. Born in 1803, Thomas entered the dry goods trade as a clerk in his teens and eventually became involved in banking and real estate. Thomas bankrolled this Italianate building in 1871 and named it after his mother’s family even though his father was about to turn 100 years of age (he has his own impressive block on Commercial Street as we shall soon see). 

Merchants Bank Block
34 Exchange Street

Few were more shocked by the devastation wrought by the Great Fire of 1866 than the directors of the Merchants Bank who had been guaranteed that their brick and iron building was “fireproof.” Matthew Stead got the call to design a new building and he dug into his stylistic toolbox for this Italian Renaissance confection featuring Corinthian pilasters framing the windows and quoins embracing the corners. Stead designed many Portland buildings in the wake of the fire but this is one of only two that survive.

Deering Block
9-13 Exchange Street

In the 1850s Nathaniel Deering owned the largest undeveloped space outside downtown Portland. Residents treated the vast primeval lands as a public park where they especially could go and admire the towering ancient oaks. With the town growing he gave some up to be divided into building lots along what became Deering Street. After the 1866 conflagration the neighborhood became the most fashionable in the city, attracting Portland’s top architects. This Deering family commercial property began life as an Italianate structure in 1867 and picked up a Colonial Revival makeover after another fire in 1898, including a bulbous Palladian window in the center. Next door, at 15-17, the Proctor Block also boasts a pair of oriel windows.   

Clapp Building
373-375 Fore Street

Developer Charles Quincy Clapp was always a keen observer of architectural trends and for this post-fire rebuild he outfitted the facade with a pair of prominent Gothic-flavored windows that enabled the three-story structure to stand out from its sea of brick-faced neighbors in Old Port. Many 19th and 20th century businesses funneled through here but during World War II it became the Seaman’s Club, a rest and relaxation destination for the thousands of sailors in Maine at the time. The Portland Seaman’s Club lasted about twenty years.

Mariner’s Church
366-376 Fore Street at northeast corner of Moulton Street

In the first half of the 19th century this was Portland’s largest commercial building, part church and part marketplace. Perhaps it was too big to burn since it stood among the ashes of the Great Fire of 1866. It was constructed in 1828 to minister to local seamen and was built big to accommodate stores to provide upkeep for the building since there was no normal congregation. The building features a Greek Revival form with Federal style fenestration. In the 1960s the old warhorse dodged the wrecking ball long enough to land on the National Reigster of Historic Places.


Thomas Block
100 Commercial Street

William Widgery Thomas, the president of Canal Bank for many years, built five commercial buildings after the city burned in 1866 - but this was not one of them. His father Elias wasn’t in the investor team of seven merchants, either. But they named the building, the largest built on the waterfront in the 19th century, after their long-time patron. Thankful, Elias then contributed the large clock in the pediment. 

United States Customs House
northwest corner of Commercial Street and Fore Street

When Alfred Bult Mullett was 32 years old in 1866 he was named head of the agency of the United States Treasury Department that designed federal government buildings. His tenure was a stormy one, wrapped in controversy for the elaborately showy Victorian piles he produced, including the Portland Customs House, one of his first projects. Mullett infused his French Second Empire confection with elements of the French Renaissance. The building uses New Hampshire granite and boasts a slate tile roof. It is considered the outstanding work of Alfred Mullett in Northern New England and like the more than 40 government buildings he shepherded to completion is widely admired today. That was not the case in Mullet’s lifetime, especially after he completed the Executive Office Building next to the White House. It was branded a “monstrosity” and so affected Mullet’s career that he took his own life in 1890 while in financial distress. Today, the Executive Office Building is considered one of America’s architectural treasures.   


Samuel Butts House and Store
332-334 Fore Street

By the time Frederic Eleazer Boothby donated this little park to the city in 1902 the Samuel Butts House and Store had been standing here for more than a century. Boothby had spent much of his working life as an agent for the Maine Central Railroad Company and was serving the second of three consecutive terms as Portland mayor at the time. In 1916, the then 70-year old Boothby would settle into the mayor’s office in Waterville. The bricks of the vernacular Federal style Butts House - only two stories at the time - withstood the flames of 1866 and so this is today the second oldest structure on the Portland peninsula. 


Milk Street Armory
20 Milk Street

At some point in the 19th century a memo must have circulated around the country to construct armories in the form of a Norman castle with crenellated towers. Most armories so equipped never had to assume a defensive position but were used for drilling national guard troops and providing recreation. That was the case with the Milk Street Armory after it was constructed in 1895 and until it was abandoned after World War II. Architect Frederick Tompson apparently received the memo but dug into his playbook anyway to add some Romanesque styling with stone trim to the utilitarian brick structure.

Deering Milliken and Company
154-166 Middle Street at southeast corner of Silver Street

Seth Milliken and William Deering started a small woolen fabrics concern in 1865 and constructed this Italianate commercial block to house operations. Cast iron was enjoying a brief surge in popularity at the time as it was easy to assemble, easy to form into ornate decoration and inexpensive - all attractive traits to the fledgling business. Deering left the business shortly thereafter to found the Deering Harvester Company, now Navistar and a major manufacturer of heavy trucks. Milliken took the business to New York City in 1868 into the heart of the textile district. When the textile industry headed south he relocated  to Spartanburg, South Carolina where the privately held company manufactures specialty fabrics and chemicals from its more than 5,000 patents worldwide. 


Storer Brothers Building
142-150 Middle Street at southeast corner of Pearl Street

Beluman, Joseph and Ebenezer Storer sailed from Northern Island for Portland in 1629. During the American Revolution, Ebenezer Storer walked to Boston to join the Patriot cause, was taken prisoner in 1780 and died of smallpox on board a prison ship in New York harbor. In the 19th century several of his offspring migrated to Ohio where the Storer family made a splash in civic affairs. His son Ebenezer stayed and constructed a wooden store several blocks down Middle Street to the west in 1799 to launch the family’s mercantile interests. This was the property of John M. Wood, United States Congresman and owner of the town’s largest newspaper, the Portland Daily Advertiser. He had planned a grand marble hotel for this site but it did not materialize before his death in 1864. Horace and Frederick Storer jumped into the retailing game here in 1881 and hired top architects Francis H. Fassett and John Calvin Stevens to design them a customer-attracting store. Their eclectic presentation includes dark brick inlays into the red brick facade; alternating bands of stone and brick to serve as window hoods; and carved terra cotta panels, including inside the classical rooftop pediments. All was for naught as the Storer Brothers failed in 1884.

Woodman Block/Rackleff Building/Thompson Block
northwest corner of Middle Street and Pearl Street

Architect George M. Harding banked these three commissions to rebuild commercial blocks after the Great Fire of 1866. The Woodman Building on the corner is the showiest although it was even more grand before the iron cresting and finials were removed from the gables in the full mansard roof. This was the stomping ground for George W. Woodman who headed Woodman, True & Company, purveyors of wholesale dry goods and carpets. The slightly overwhelmed Rackleff Block holds its own with a High-Style Italianate presentation, highlighted by a graceful rounded corner. The cast iron storefronts of both buildings boast some of the best work from the local Portland Company foundry. Harding amped up the ornamentation once again with another French Second Empire design for the Thompson Block across narrow Church Street. He starts with a granite base, lays on the freestone trim in two colors and finishes with alternating bands of red and gray slate on the mansard roof. The extensive ornamentation is cut to represent the leaves and acorns of an oak tree, no doubt to symbolize the strength and resolve of Portland after the Great Fire. Taken together, this is one of the finest blocks of 19th century architecture in Northern New England.


Edward Thaxter Gignoux United States Courthouse
156 Federal Street at southeast corner of Pearl Street

When the new United States established the Judiciary Act of 1789 it created 13 district courts, including one in Maine which was still part of Massachusetts. The Court was mostly Portland-based but Pownalborough and Wiscasset and Bangor all got a swing at it during the 19th century. In 1911 the federal government provided Portland with an impressive Italian Renaissance Revival seat of justice, courtesy of Supervising Architect of the Treasury, James Knox Taylor. The court was named for son of Portland, Edward Thaxter Gignoux, after his death in 1988. He had been appointed a United States District judge by Dwight D. Eisenhower thirty years earlier and had presided over the trial of the Chicago Eight, protesters accused of disrupting the 1968 Democratic National Convention in Chicago.

Cumberland County Courthouse
142 Pearl Street at northeast corner of Pearl Street

Cumberland County, named for Prince William Augustus, the Duke of Cumberland, received its first house of justice in 1786. This is courthouse number five, started in 1908 after fire destoryed a Francis H. Fassett-designed model. F.W. Cunningham & Sons of Portland handled the construction work, as they did for the U.S. Courthouse across the street. Architects Guy Lowell of Boston and George Burnham of Portland teamed up on the four-story granite Beaux Arts home for the Maine Supreme Court. the courthouse was expanded substantially to the east and north in the 1980s, but without the fluted Doric columns.