If you Google “Portsmouth” the Virginia town at the mouth of the Elizabeth River comes up first. But while both towns were named for the port in England, the colony of the Province of New Hampshire was actually founded (although he never actually made it this far south from his landing in Newfoundland) by the captain of the English port, John Mason. In fact, Portsmouth, New Hampshire was settled (1630) and fortified more than 100 years before its Virginia counterpart.

The natural harbor formed by the Piscataqua River has been compared to San Francisco for its advantages, save for a nasty current, and the early residents wasted no time in exploiting the location. Shipbuilding and trade made Portsmouth a favorite stop in Colonial times. And after America won its independence Portsmouth continued to be an important player in the young nation’s affairs. Portsmouth native John Langdon functioned as Acting President of the United States before giving the oath of office to George Washington. Portsmouth was generally considered the wealthiest city in New England and in the first census in 1790 it was the 14th most populous city in the country. Portsmouth would not drop out of the Top 20 until 1830. 

The sea captains and merchants plowed their profits into their houses. As one observer noted, “The builders of Portsmouth had an eye for style. Tall, square, and many with hip roof, the mansions were the work of builders who were ever attentive to the molding of chimney caps, to the sweep and proportion of granite steps and coping, and to the detail of iron posts and hand-wrought designs on the railings. Topping many a house is the white-railed captain’s walk, from which the merchant could look into the bay and eagerly watch his ships slip home. Not so ornate as the houses of Salem, or so imposing as the Colonial mansions of Virginia, these dwellings show a delicacy of design that larger houses often lack.”

Fire was the enemy of these early American showplaces and Portsmouth suffered more than most. A 1781 blaze lay waste to important swaths of downtown. A Christmas night fire in 1802 completely destroyed entire blocks of Market Street and another in 1806 crippled Bow Street. Finally a conflagration in 1813 burned across 15 acres of the city and claimed nearly 300 structures. After that the New Hampshire legislature passed the Brick Act that forbade the erection of any wooden building higher than 12 feet, which displeased plenty of folks. Wood was cheaper than stone and brick and not everyone was rich. And the town was chock-full of skilled tradesmen who made their living shaping wood.

The result is two historic Portsmouths, one built of wood and the other built of brick. To launch our explorations of the “Old Town by the Sea” we will begin at the center of the downtown core in a sea of bricks before fanning out into the wood...  

1.
Portsmouth Athenaeum
9 Market Square

The center of this dominant downtown Portsmouth block was created in 1805 by builder-architect Bradbury Johnson. Johnson, born in 1766, hailed from Epping, New Hampshire where he trained as a joiner. Working from English builder’s sourcebooks, Johnson’s early efforts were mostly in Exeter and his base in Saco, Maine. After central Portsmouth was ravaged by fire he issued plans for a new four-story brick headquarters for the New Hampshire Fire and Marine Insurance Company that boasted Palladian windows and Federal-style two-story pilasters above. He gave the roof a tar-and-gravel composition to guard against further fires. The Portsmouth Athenæum Society, a subscription library, was founded in 1817, using rented rooms in town. After the insurance company went bankrupt in 1823 a scheme was engineered by subscribers to obtain the building for the library - a natural transition since the first floor had always operated as a reading room for local business people. The Athenæum collection, which includes over 50,000 items, grew and spread into surrounding buildings on the block.

ACROSS THE STREET IS...

2.
North Church
2 Congress Street

This exuberant Italianate church building is the third on this site. An early 1671 Protestant meeting house was replaced in 1713 with a parish church here. Daniel Webster was a prominent member of the congregation and George Washington attended services there. That church stood until 1835 when it was replaced with a three-story sanctuary. But less than two decades later the Congregationalists were calling on John D. Towle and Albert F. Bellows of Massachusetts for a new building. The current church was completed in 1852 with a price tag of $30,000. The 180-foot spire, which can be seen across the city, features multiple tiers and elaborate bracketing. In 2006, during a renovation, an electrical storm sent the steeple and thousands of pounds of scaffolding thundering down into Market Square. No one was hurt and the rapidly-formed Market Square Steeple Fund restored Portsmouth’s signature piece of skyline architecture.  

WITH NORTH CHURCH ON YOUR RIGHT, WALK DOWN PLEASANT STREET.

3.
New Hampshire Bank Building
22-26 Market Square

The New Hampshire Bank was incorporated on January 3, 1792 as the first bank in the Granite State. Its building here replaced an earlier headquarters that burned in the great fire of 1802. Spearheaded by the efforts of 58-year old Eliphalet Ladd, one of the most prosperous merchants in town, the premises were rapidly rebuilt. From 1803 until 1998 it served 11 masters and was the oldest bank building in continuous use in the United States. The Neoclassical facades seen today were early 20th century affectations when the Portsmouth Savings Bank and First National Bank Building were quartered here. Several lawyers of note clocked in for work in the office space above the banking hall, including Governor Levi Woodbury and his protege, future 14th President of the United States, Franklin Pearce.

4.
New Hampshire National Bank
3 Pleasant Street

The New Hampshire National Bank took its first deposits in 1855 as the New Hampshire Bank (the previous New Hampshire Bank next door having expired in 1842). In 1865, under the guidance of Peter Jenness, it became a national bank under charter number 1052. As a national bank it was entitled to print currency and churned out $2,925,800 before shutting down printing operations in 1935 - a long time and considerably more activity than a typical national bank. The company moved into this three-story Italianate-flavored vault in 1860. It too picked up a classical freshening that included marble lintels with keystones above the windows and an Ionic-themed entranceway. 

5.
Rockingham County Bank
15 Pleasant Street

The Rockingham Bank was ushered into existence in 1813 and remained a family affair for nearly its entire 92 years of existence before expiring in 1905. Jacob S. Pickering was cashier until 1849 and then was replaced, in turn, by his son and grandson. The bank moved into this handsome Italianate structure in 1857, an early design of Shepard S. Woodcock. Woodcock was born in Sidney, Maine in 1824 and left for Stowe, Massachusetts at the age of 17 to apprentice as a carpenter. During his ten years in the trade he studied architecture and landscape design. Woodcock would go on to design more than 150 churches and 50 schoolhouses, in addition to his commercial and residential work. The granite Neoclassical skirt on the first floor is courtesy of Piscataqua Savings Bank, who moved in during 1924 and used the addition to weld the old Rockingham Bank stylistically to the Exchange Block, an 1820 Federal-styled building, next door. The Piscataqua Savings Bank was incorporated in 1877 under the auspices of Ichabod Goodwin, a shipping magnate and 27th governor of New Hampshire. The bank vault in Piscatagua’s new headquarters was upgraded from brick to steel and customers could enjoy a public telephone and a “retiring room for ladies” with a resting couch and potted palms. 
   
6.
United States Custom House
40 Pleasant Street at southwest corner of State Street

Ammi Burnham Young was born in Lebanon, New Hampshire in 1798, the son of a master builder. With a flair for drawing and mathematics, Ammi started in his father’s trade at the age of 14 but soon went to Boston to work under leading architect-engineer Alexander Parris. Young hung out his own shingle in Burlington, Vermont in 1830 where he was an enthusiast for the Greek Revival style. His design for the Vermont State House springboarded him into the position of Supervising Architect of the United States Treasury in 1852. By this time Young was a cheerleader for the emerging-Italianate design being championed by Philadelphia architect John Notham. He designed many elegant Customs Houses in the Italian Renaissance fashion and Portsmouth’s arrived in 1860. The beautifully proportioned building is composed almost entirely of granite - right down to the decorative chimneys protruding from the roof of the three-story former federal building. Young would not build many more like this; he retired from his Treasury post in 1862.  

TURN RIGHT ON STATE STREET.

7.
South Church
292 State Street

Northern New England had not seen many grand scale granite buildings when this Roman-inspired South Unitarian Church rose between 1824 and 1826. The hammered stone did not come from Granite State quarries, however, but from Rockport, Massachusetts. The entrance portico is fronted by a quartet of Tuscan columns which introduce the understated classicism of the composition. The congregation formed in 1713 after splitting with the folks in the North Church; they became Unitarian in 1819.

RETRACE YOUR STEPS TO PLEASANT STREET AND TURN RIGHT. 

8.
Treadwell Jenness House
93 Pleasant Street

This exquisite Federal style house was one of the first grand mansions constructed in Portsmouth under the strict requirements of the 1814 Brick Act to try and arrest the destruction of downtown by fire. One of the more celebrated victims of those fires had stood right here - the baronial estate of the High Sheriff of the Province of New Hampshire in the pre-Revolution 1700s, Thomas Packer. Packer carried out the execution of Ruth Blay in 1768 for the crime of Concealment - giving birth in hiding to an illegitimate child who did not survive and was therefore assumed to have been murdered. For that reason some have claimed that the mansion erected by the widow of merchant Robert Treadwell in 1818 and subsequently occupied by another merchant family, the Jennesses, is haunted. In the early 1900s Elias G. Merrick purchased the property and ran the Hotel Merrick here, which gave the spirits all the more cause for consternation. The winged sculpture above the fanlighted entrance is a modern affectation. Daniel Webster once lived in a now-gone residence across the street. 

9.
Governor John Langdon Mansion
143 Pleasant Street

The Langdons were some of the earliest settlers near the mouth of the Piscataqua River and by the mid-1700s several members of the clan were among the wealthiest of Portsmouth merchants. John Langdon, born in 1741, earned his place in the pantheon of the nation’s Founding Fathers by pledging much of his wealth to the cause for liberty and participating in the seizure of British materiel from Fort William and Mary. His cousin Samuel then transported the booty to the Continental troops at Bunker Hill. Langdon was a member of the Second Continental Congress and active throughout the Revolution. Afterwards he served two terms as President of New Hampshire and was a United States Senator from New Hampshire where he acted as first President of the Senate. Langdon also found time in 1784 to construct this sumptuous residence which George Washington, who dined here several times, proclaimed the handsomest seat in Portsmouth. John Langdon lived here until his death in 1819 and the property funneled through several hands before coming into the possession of Langdon descendants in 1877. They hired McKim, Mead & White of New York, the nation’s foremost Gilded Age architects, to transform the mansion into the Colonial Revival showplace in front of you. The Langdon house was declared a National Historic Landmark in 1974.

10.
Captain Thomas Thompson House
179 Pleasant Street

Thomas Thompson was a successful shipbuilder in town who was called upon by the Continental Congress to construct and captain a warship to harass British supply schooners on the Atlantic Ocean. One of 13 ships authorized for the new United States Navy in 1775, Thompson’s 32-gun frigate was christened the USS Raleigh. The boat launched from Portsmouth on August 12, 1777 and quickly teamed up with a former merchant ship now outfitted with 30 guns, the USS Alfred. Together they captured their first prize three days later. The two ships completed a mission to score military stores from France but the slower Alfred was seized by British ships in the West Indies on the return voyage. The Raleigh made it back to New England but Thompson was found at fault for not rescuing the Alfred and relieved on duty. The Raleigh was eventually captured in Penobscot Bay and refloated as a British warship in the Royal Navy before being decommissioned and sold in 1783. As the first United States Navy warship commissioned at the Portsmouth shipyard she is depicted on the Seal of New Hampshire. Thompson emerged from the war to build this Georgian-styled residence under a hipped roof in 1784. His neighbor, Governor Langdon, made him the Colonel of the Regiment of Artillery. Thompson died in 1809 and the property stayed in his family for many years after that.

11.
Jacob Wendell House
212-222 Pleasant Street at northwest corner of Edward Street

This property looks like big brother and little brother but Jacob Wendell, who was born in Portsmouth in 1788, was scarcely alive when these houses first became neighbors. The Georgian-styled house at Number 212 dates to 1750 and was occupied by the family of sea captain Richard Salter Tibbetts and his wife Sarah Frost Tibbetts from 1790 until 1852. Jeremiah Hill built the slightly larger but stylistically similar abode in 1789. Wendell, who made his fortune in the Russia and West India trade before becoming an early player in New Hampshire textile manufacturing, purchased the property in 1816. After  he died in 1865 his estate attached the two properties and made some subtle changes to unify their appearance (two dormers added to the Tibbetts place). The Wendell House was known around town in the early 20th century for its intricate Chinese puzzle garden in the rear. Look up to see the whale oil lamp motif carried through the pediments on the original Wendell House.

12.
Governor John Wentworth Mansion
346 Pleasant Street

There is no name older and more distinguished name In Portsmouth than Wentworth. When John Wentworth became the last Royal Governor in the New Hampshire colony he was already the fifth generation of Wentworths in town. Wentworth was a popular governor who built roads and the Portsmouth Harbor Lighthouse, divided New Hampshire into five counties and chartered Dartmouth College. He also modernized the local militia which did not work out in his favor when he attempted to maintain British control in the early days of the Revolution. On June 13, 1775 this house was surrounded by a mob and Wentworth escaped out the back and onto a boat on South Pond. He never saw this house again. He sailed to England in 1778 and eventually became the first civilian governor of Nova Scotia. The impressive house was constructed in 1763 for a prosperous merchant, Henry Appleton, who sold it to Mark Hunking Wentworth for 4000 pounds a year later. In 1911, 16th generation Wentworths - siblings Susan and Charles - bought the house and turned it into a care center for chronically ill children and seniors. It is now know as Wentworth Senior Living.

TURN LEFT ON MANNING STREET. TURN RIGHT ON MEETING HOUSE STREET. TURN RIGHT ON MEETING HOUSE HILL.

13.
South Meeting House
southwest corner of Meeting House Hill and Marcy Street

As you have noticed the South End of Portsmouth, the city’s oldest area, is totally residential, save for this structure. Beginning  in 1731 the South Parish meeting house stood here. The City bought the property in 1863 and tore the building down. In its place was planned “a ward and school room.” Local carpenter-architect Isaiah Wilson was paid $84.65 for a simple vernacular building to do the job and he crafted a basic Italianate design infused with Greek Revival elements. The total budget for the project was $9,600.

FACING THE MEETING HOUSE, TURN LEFT. TURN LEFT ON HUNKING STREET.

14.
Tobias Lear House
49 Hunking Street

Here is more vernacular architecture, this time in the Georgian style. Tobias Lear III raised the simple structure around 1740. His son would become the shipwright responsible for outfitting the Ranger, an 18-gun Continental Sloop-of-War built in Portsmouth for John Paul Jones. The fifth Tobias Lear took a degree from Harvard in 1783 and got one of the better jobs after graduation as Private Secretary to George Washington. Lear remained the close aid to Washington until the first President’s death in 1799. During a visit to Portsmouth the President took time to visit here and pay respects to his Secretary’s family. The Lears stayed in the home while the neighborhood declined until 1860. The house became a tenement property until Historic New England rescued it in 1935. 

TURN LEFT ON MECHANIC STREET.

15.
Wentworth-Gardner House
140 Mechanic Street

While the Tobias Lear House is a fine example of simple Georgian house design, the Wentworth-Gardner House is considered one of the finest high-style Georgian buildings in New England. Both are operated together as a museum. Mark Hunking Wentworth had the house constructed in 1760 as a wedding gift for his son, Thomas. Thomas died in 1768 and his widow Anne and five children moved to England. Major William Gardner, former Commissary for the Continental Army, bought the property in 1792 and lived the last four decades of his life here. One owner not listed on the marquee is Wallace Nutting, a Congregational minister and leading cheerleader for the Colonial Revival movement of the early 1900s. Nutting bought the house in 1915 and flipped it to the Metropolitan Museum of Art three years later. The Met either planned to strip the interior for museum pieces or haul the entire house to Manhattan for display in its courtyard. Neither came to pass. Instead the town raised up and created the museum, hiring the prestigious architectural firm of Cram and Ferguson, founded in 1889 and still at it today, to spruce up the old treasure.

16.
Point of Graves Cemetery
southwest corner of Mechanic Street and Peirce Island Road

John Pickering owned all of South Portsmouth in its formative days. When he died in 1669 his son buried him here within sight of the Piscataqua River. He then donated just under half an acre around his father’s grave as a burial ground for the city - so long as his family could graze their cattle here. By the early 1900s the cattle had long since stopped eating and the town’s oldest burial ground was overgrown and in disrepair, much like Pickering’s old South End around it. A century later the Point of Graves Cemetery, like the South End itself, is trim and tidy once again. There are several ancient tombstones of note in the small burial ground; one of the favorites is the skull and crossbones on Captain Tobias Lear IV’s headstone.

ACROSS THE STREET, FOLLOW THE WALKING PATH BESIDE THE RIVER INTO...

17.
Prescott Park
105 Marcy Street

Two who were instrumental in helping to revitalize this part of town were sisters Josie and Sarah Prescott. In the 1940s the Prescotts, both public school teachers, began investing their trust fund from their brother of $500,000 into clearing properties along the Piscataqua River. This ten-acre waterfront park is their legacy. Two warehouses remain on the waterfront: the timber-frame Sheafe Warehouse from the 1740s and Abraham Shaw’s Wharf from 1806. The Sheafe Warehouse was constructed just out of the reach of high tide on interlocked tree trunks known as “cobwork.” Charles H. “Cappy” Stewart, the most high profile of the town’s waterfront bordello operators, ran his illicit empire from here in his heyday in the early 1900s. Between 1897 and 1912 there were usually at least a dozen houses of ill repute close by. Forty flower beds were laid out in the park by the University of New Hampshire as “Trial Gardens” in the 1970s and the brick walkways meander past several fountains, including the Charles Hovey Fountain with a bronze sculpture of Neptune by Allen Frederick Warren.

WALK TO THE WEST EDGE OF THE PARK BORDERING MARCY STREET. THE FLAGPOLE IS...

18.
Liberty Pole
Prescott Park

Long before the Prescott sisters this ground was a part of the Piscataqua River known as Puddle Dock Cove. There used to be a small bridge here to access Strawberry Banke and a flagpole stood beside it. In the 20th century the cove, degrading with silt and garbage, was filled in. During the squabbling over the hated Stamp Tax and other levies “without representation,” the local insurgents known as the Sons of Liberty flew a banner from the pole in 1766 proclaiming “Liberty, Property and No Stamp.” In 1824, with Patriot days becoming a memory, the town installed a permanent 85-foot tall “Liberty Pole,” complete with a gilded eagle carved in Boston by Laban Beecher on top. That pole was replaced with a 110-footer in 1899 as the filling in of the cove began. The eagle lasted into the 1970s before it was replaced with an gold-painted pine eagle. That unworthy bird gave up a wing to a wind storm and was retired in favor of an avian mahogany symbol - 70 pounds and four feet tall.  

THE BRICK BUILDING TO THE NORTH FACING THE STREET IS...

19.
Players’ Ring Theater
Prescott Park

This building from 1833 was the headhouse for the Portsmouth Marine Railway Company. The company was formed by a consortium of local merchants to facilitate the repair of cargo ships. A set of tracks was laid between the waterfront and the machine house. With the help of two horses the machinery could, as the company promoted, “draw vessels of 500 tons and upwards, entirely out of the water, placing them in a situation where any part of their hulls can be inspected or repaired with great dispatch.” This proved a much more efficient repair strategy than beaching ships on their sides. The Portsmouth Marine Railway Company chugged into the 1850s before Leonard Cotton bought the business and operated it privately for another two decades. Afterwards the headhouse did duty as a private residence, a fish store and, since 1992, home to The Players’ Ring Community Theater. The all-volunteer organization puts on performances in its “black box” stage that seats 75.  

ACROSS FROM PRESCOTT PARK IS... 

20.
Strawberry Banke
Bounded by Court and Marcy streets and both sides of Hancock and Washington streets

There were so many wild berries growing here when the first Portsmouth settlers started clearing land in 1630 that colonial administrator Walter Neale named the town’s first neighborhood Strawberry Banke. After more than 300 years of everyday living Strawberry Banke became an outdoor museum in 1965 and a repository for neighborhood buildings spared the wrecking ball. There are 39 restored buildings from the 1700s and 1800s - most on their original foundations - on the grounds; many are open to the public for inspection. The earliest was constructed in 1695.

WHEN YOU ARE FINISHED EXPLORING STRAWBERRY BANKE RETURN TO MARCY STREET AND TURN LEFT.

21.
Oracle House
38 Marcy Street

This gambrel-roofed house looks as if it has been anchored on this pleasant corner forever but in fact it was already almost 240 years old when it was brought here in 1937. Constructed by Royal Navy officer Richard Wibird in the first decade of the 18th century near North Church, the house takes its name from The Oracle of the Day, the first daily newspaper in New Hampshire. Charles Peirce disseminated the news of Portsmouth in this house from 1793 until 1799. The Oracle House is considered one of the oldest houses in New England. 

CROSS STATE STREET AND TAKE THE SHORT STAIRWAY UP INTO...

22.
Memorial Park

Crossing the Piscataqua River at this point, a river whose waters run so deep and so swift that it never freezes over, is the second Memorial Bridge. In 1923 Maine, New Hampshire and the federal government chipped in $1.5 million to build a vertical lift bridge as a reminder of the sailors and soldiers who “participated in the World War 1917-1919.” The Memorial Bridge was the tallest lift bridge in the United States. It was also the first toll-free bridge across the dangerous tidal river. Due to deterioration the original center span was demolished in 2012 and replaced with a similar structure. Cutting the ribbon at the 2013 dedication service was Eileen Foley who ninety years earlier had performed the same duty as a five-year old girl. In the intervening years her mother Mary Carey Dondero became the first female mayor of Portsmouth and Eileen Foley was elected as mayor eight times - becoming the longest serving mayor in city history. The triangular park was added with the new bridge, honoring with granite slabs Americans who have served in the military, regardless of conflict.

CONTINUE ACROSS TO THE CORNER OF BOW STREET AND DANIEL STREET. TURN RIGHT ON BOW STREET.

23.
Portsmouth Brewing Company Warehouse
121 Bow Street

Three hundred years ago this curving street was a walking path through a transition area between Portsmouth’s busiest waterfront areas. After the fires of the early 1800s Bow Street became a bustling street in its own right, lined with brick warehouses. 

Portsmouth came a little late to brewing in relation to its fellow colonies. By the time Samuel Wentworth obtained the first license in New Hampshire to brew beer in 1670, New York and Boston had enjoyed brewed beer for thirty-plus years. The town’s first commercial brewery did not open until Robert Trail’s venture in 1766. By the 1870s there were 4,131 breweries operating in the United States and Portsmouth had three major thriving operations: the Frank Jones Brewing Company, the Eldredge Brewing Company and the smallest of the trio, the Portsmouth Brewing Company. Portsmouth Brewing crafted India pale ales, old brown stouts and their signature Portsburgher lager beer. When Prohibition ended in the 1930s fewer than 1,000 of those brewers re-opened their taps; Portsmouth Brewing was not one of them. The original brick warehouse from 1896 has been repurposed as retail space and a home for the Seacoast Repertory Theatre. 

TURN LEFT ON CHAPEL STREET.

24.
St, John’s Church
105 Chapel Street

Alexander Parris, then operating in Portland, Maine, gave New Hampshire its first brick church here in 1807. Still in his twenties at the time, Parris often aped the work of America’s first starchitect, Charles Bulfinch. This is considered the oldest surviving work of Parris who would go on to become prominent as an engineer and architect in Boston. Parris would also design the docks of the Portsmouth Navy Yard. The Anglican congregation had lost its Queen Chapel from 1732 in the Great Fire of 1806 and tapped the town’s best talent to execute Parris’ design. James Nutter, called “the head of his craft” was on hand as a joiner and wood carvings were contributed by William Dearing, the consensus best carver on the seacoast. Thomas Thompson, as Grand Master of Masons in New Hampshire, laid the cornerstone on June 24, 1807. The St. John’s Parish Hall next door arrived in 1953 and its Colonial Revival style was meant to mimic the church.

25.
Macpheadris-Warner House
150 Daniel Street at northeast corner of Chapel Street

Archibald Macpheadris was an ambitious Scottish sea captain and merchant who switched his home port from Boston to Portsmouth in 1714. He bought this property in 1715, a good place to raise the four-month old lion cub he had just brought back from Spain. Macphreadis was prospering and had money to throw around. He was the principal investor in the Lamprey Iron Works, the first in the state. And he spared no expense with his house that started in 1716. Master builder John Drew, who cut his teeth on London streets was put in charge and he directed the laying of bricks in a Flemish bond pattern eighteen inches thick for the exterior walls. The new Georgian house was considered the finest in Portsmouth and three hundred years later is the oldest urban brick residence in Northern New England. For over 200 of those years, until 1931, the house remained in the family.

TURN RIGHT ON DANIEL STREET.

26.
Army and Navy Association Building
143 Daniel Street

America’s oldest continually operating shipyard was amped up during World War I, tasked with constructing the first ever submarines in a United States naval yard. This Colonial Revival hall was constructed as a recreation center for military personnel and remained active through World War II. In civilian life the building has done duty as a community center.

27.
Old High School and City Hall
126 Daniel Street

Bridget Graffort can be considered one of the first Portsmouth residents to be considered a forward-thinking steward of her town, although she seems to reap little credit for her efforts. She gave a strip of land to the Town of Portsmouth that ran from Market Street to the Piscataqua River in 1700; it was called Grafforts Lane then but became Daniel Street (her first husband, Thomas Daniel). Graffort also donated this plot for the construction of a school but her bequest was ignored and the land traded for a more central location. Instead, due to unrelated circumstances, the high school, built in textbook Italianate style, was raised here in 1858. There was apparently never any push to name it Graffort School. It was the city’s third school for upper classes and the first that both boys and girls attended together, although the genders did not mix in classrooms until the 1870s. More room was needed in 1905 and the school moved on, to be replaced by the city government. Today, the building on Bridget Graffort’s land trundles on as office space.

28.
Old Custom House
59 Penhallow Street at southeast corner of Daniel Street

In the wake of the Great Fire of 1813 Langley Boardman and John Abbott erected this Federal-styled brick building with a rounded corner in 1816. They then sold the property to the United States government for use as a Customs House. Look up to see the wooden sunbursts inlaid into Palladian windows across the second story. The post office put out mail on the first floor and the customs department was run out of the second floor. That upper floor was expanded in 1838 by master carpenter Thomas Martin who also installed a marble name badge on the Penhallow Street elevation. The government left in 1850 but the handsome location has attracted a steady stream of businesses ever since. 

29.
Thomas J. McIntyre Federal Building and Post Office
62 Daniel Street at northeast corner of Penhallow Street

Here’s a totally different styled federal building from 150 years later. The post office from 1967 was added to the Portsmouth streetscape by Manchester architects Nicholas Isaak and Richard Koehler. Isaak and Koehler were two of 130 men and women who earned architectural degrees from the University of New Hampshire between 1918 and 1944, the year the program was shut down. Of those graduates, only 18 ended up practicing in the state. Here they employed what was called the New Formalist style that intended to honor the Colonial architecture seen on the streets of Portsmouth while introducing new technologies and design elements. 

TURN RIGHT ON PENHALLOW STREET AND CROSS BOW STREET ONTO CERES STREET TO WALK ALONG THE OLD PORTSMOUTH WATER FRONT. AT THE END OF THE NARROW STREET, TURN LEFT ON MARKET STREET.

30.
Moffatt-Ladd House
154 Market Street

Befitting one of the wealthiest men in the New Hampshire colony, trader John Moffat built one of Portsmouth’s best pre-Revolutionary War houses here in 1763. It boasts a wood-shingle clad hipped roof that supports a widow’s walk protected by a balustrade with urn finials. Each floor of windows is given a different decorative treatment. The house was envisioned as a wedding gift for his son but Moffat bought it back in 1768 and lived here with his daughter and son-in-law William Whipple, a Revolutionary War general and signer of the Declaration of Independence. The horse chestnut tree growing in the yard began as seeds Whipple collected during his time in Philadelphia.

TURN RIGHT ON HANOVER STREET. TURN LEFT ON FLEET STREET.

31.
National Block/Odd Fellows Hall
40 Congress Street at southeast corner of Fleet Street
 
Frank Jones brought his entrepreneurial spirit to Portsmouth in 1848 when he was 16 years old. He apprenticed in his brother’s stove store, just long enough to take over the operation. Over the years you could find Jones involved in manufacturing buttons, selling shoes, publishing, banking, milling,, hotels, insurance and steamships. In 1858 Jones and John Swindell started a brewery but within a few months Jones had not only bought Swindell’s share of the business but had his ale recipe as well. The Frank Jones Brewing company was not only the largest brewery in Portsmouth, it was the largest employer. In the 1880s no brewer in the United States produced more ale than Frank Jones. In 1878 Jones, who had found time to serve two terms as Portsmouth mayor, bankrolled the construction of this French Second Empire commercial block. Jones money paid for the highest quality brownstone and brick. The International Organization of Odd Fellows moved into the upper floors and held lodge meetings here until 1989. The building stands as a monument to Frank Jones’ career - not that it is necessary. When Jones died in 1902 his tombstone was the largest ever carved in Portsmouth.

TURN RIGHT ON CONGRESS STREET.

32.
McIntosh Building
90 Fleet Street at southwest corner of Congress Street

Portsmouth received this skyscraper wannabe in 1919 when “Complete Home Furnisher” D.H. McIntosh put $75,000 into the creation of this seven-story store building. The classically-flavored McIntosh Building follows the Chicago Style school of design with orderly fenestration and a minimum of showy ornamentation.

33.
Franklin Block
75 Congress Street at northwest corner of Fleet Street

There has been plenty of tinkering through the years but this is the largest Victorian-era building still standing in Portsmouth. Celebrated Boston architect Arthur H. Vinal drew up the plans in 1879, although he was only four years into that career when he won this commission. The money man for the Franklin block was Alfred Stavers who conducted a crockery and china store in one of the six retail slots in the building. The Franklin Block rose from the rubble of the Franklin House that had stood here for decades and burned in a spectacular morning fire on May 8, 1879.

34.
Kearsage Hotel
104 Congress Street at southwest corner of Chestnut Street

This graceful Second Empire structure with bow-fronted bays was built in 1866 as a private two-family residence but was quickly converted into a hotel. When owner Joshua Winslow Peirce made the switch to a commercial property he named his guest house after the Civil War sloop, the USS Kearsage, that was built in the Portsmouth Naval Shipyard and famously sunk the notorious Confederate raider, the CSS Alabama, at the Battle of Cherbourg in the waters off France on June 19, 1864.

35.
Montgomery Ward Building
138-140 Congress Street

This rare dash of Art Deco styling in Portsmouth came with the arrival of Montgomery Ward’s. In its retailing war with Sears & Roebuck, Ward’s staked out the ground on small town Main Streets with modest-sized stores such as this one. The company was late to recognize the shift to suburbia and when it finally went on a building spree in the late 1950s, it was too late. This Montgomery Ward’s store shuttered in 1973.

TURN LEFT ON MIDDLE STREET.

36.
Discover Portsmouth Center
10 Middle Street

The Portsmouth Historical Society uses two Federal-styled buildings, the Benedict House and the Portsmouth Academy, as an information center. The Portsmouth Academy was the handiwork of designer-builder James Nutter in 1809 who no doubt did a thorough study of existing pattern books. The academy was a private boys’ school before being given to the city in 1868 as a public school. It then housed the Portsmouth Public Library which was linked to the Benedict House, erected by Thomas Morton in 1810, via an ell in 1954. Portsmouth checked out its books here for over 100 years before the library moved in 2006.

37.
John Paul Jones House
43 Middle Street

How important is naval hero John Paul Jones to the American story? He rented a room in this boarding house for a few months in 1777 and not only is the house named for him but it has been declared a National Historic Landmark as the only known structure still surviving that has any connection with Jones. He was staying here the check on the construction of his warship Ranger at Badger’s Island. The Jones connection is a relatively recent phenomenon; a century ago this was the Samuel Lord House. Lord was just a banker in town. Lost in the shuffle is the original owner, sea captain Gregory Purcell, who built the fine Georgian house in 1758. It was his widow, Sarah, who cashed Jones’ rent checks. The Portsmouth Historical Society has been responsible for the property since 1920.

38.
Granite State Fire Insurance Company
85 Middle Street

After a disastrous fire at the Rockingham House in 1884 and shenanigans from his insurance company in the aftermath, brewer Frank Jones agitated in Concord for legislators to mandate that insurers fully cover policies on their buildings. Fifty-eight companies shut down operations in the state in an attempt to get New Hampshire to change the law. Instead local businessmen like Jones jumped in to fill the void. His Granite State Fire Insurance Company erected this confidence-inspiring headquarters from granite and brick in the Classical Revival style in 1924.

39.
Parrott House
132-134 Middle Street

It was said that Gridley J.F. Bryant was the most commissioned architect in the history of Boston. At the height of his career he was juggling the most business in New England and this double house was constructed right in his prime - in 1866 when Bryant was 50 years old. The client was William Flagg Parrott who hailed from a seafaring family that included his father, John Fabyan Parrott, a United States Congressman and Senator, his uncle Enoch Greenleafe Parrot, a United States Navy rear admiral, and a brother, Rober Parker Parrot, inventor of rifled artillery that was used extensively by the union in the Civil War. Bryant delivered an exemplary French Second Empire brick confection with brownstone trim and a slate mansard roof.

ACROSS THE STREET IS...

40.
Ebenezer Thompson House
145-47 Middle Street

Ebenezer Thompson made so much money in shipbuilding in his native Durham, New Hampshire that he was the largest taxpayer in town. He came to Portsmouth at the turn of the 19th century where he bought up land and bankrolled merchant ships. He constructed this grand three-story, five-bay abode in the Federal style in 1801. Thompson, who was rumored to have lost $40,000 in one night during the Great Fire of 1813, apparently liked to play hard ball in his business dealings and must have found himself before a judge regularly as he was remembered for being a “fluent speaker, used to pleading his own cases in court.”  

NEXT DOOR TO YOUR LEFT, SET BACK FROM THE STREET, IS...

41.
Peirce Mansion
1 Court Street at southeast corner of Middle Street

In 1799, the short distance you have just walked out of town was considered to have put you in the sticks, surrounded by hayfields. The only structure you would have seen would have been hay scales the city installed. So they called this Haymarket Square. And then that year John Peirce arrived. He was the first to build on Haymarket Square, with a standout Federal design crowned by a projecting central tower. Peirce, a nephew of Mark Hunking Wentworth, was one of the town’s straightest shooting businessmen and others soon followed to erect statement mansions of their own, as you have seen around the square. Peirce had not backed the rebellion in the colonies but remained neutral and when President George Washington paid a visit to Portsmouth it was the old Loyalist who was chosen to shepherd him around town. The Peirce Mansion remained in the family until the 1950s when it was sold to Middle Street Baptist Church next door which moved the house back from the street.

42.
Middle Street Baptist Church
18 Court Street

The Portsmouth Baptists got serious about organizing in 1826 and constructed a sanctuary on this site. The current church building dates to 1956 and the only thing remaining from the congregation’s formative days is the bell that has rung since 1828.

WALK AROUND THE HAYMARKET SQUARE CIRCLE AND RETURN TO STATE STREET. TURN RIGHT.

43.
Rockingham Hotel
401 State Street

This is the Portsmouth hotel where United States Presidents - seven of them - would sign the guest register while visiting New Hampshire. Deep in the bones of this exuberant Victorian guest house is the mansion of Woodbury Langdon from 1785. When the property was sold in 1830 it was transformed into an inn called the Rockingham House. Alemaker Frank Jones bought the Rockingham House in 1870, determined to present guests with the most elegant stay in New England. And then the Rockingham House burned in 1884 - the unsatisfactory resolution of his claim is what led Jones to found his own insurance company. Jones rebuilt the Rockingham in a Queen Anne style according to plans from architect Jabez Sears; a pair of copper oriel windows dominate the facade. Sculpted terra cotta ornaments are meant to symbolize the four seasons and in the rooftop pediments reside busts of Jones and Langdon. Four gilded lions - the King of the Jungle was Jones’ personal symbol - guard the entrance. The hotel era for the Rockingham came to a close in the 1970s and it is now a condominium and restaurant, with diners noshing in Woodbury Langdon’s old dining room.

TURN LEFT ON FLEET STREET. TURN RIGHT ON CONGRESS STREET TO RETURN TO THE TOUR STARTING POINT IN MARKET SQUARE.