Its location on important transportation routes has shaped Great Barrington from before written history. When the Mahican Indians lived in the meadows here the area was called Mahaiwe, meaning “the place downstream.” In colonial times when the Dutch and English settled here beginning in 1726, it lay on the New England Path, which connected Fort Orange near Albany, New York with Springfield and then Massachusetts Bay in 1844. In a key moment in the American Revolution, Henry Knox used that path to haul cannon from Fort Ticonderoga to Dorchester Heights to end the British siege of Boston.

Great Barrington was by then an important hub, having been designated the Berkshire County seat in 1761. The town name came most probably came from Lord Barrington, an English aristocrat who was minister of war for his friend Prime Minister William Pitt, whose name Pittsfield took at the same time. The railroad arrived in 1842 spawning a growth spurt in trade and, following the Civil War, as a summer destination for refugees from the big northeastern cities. Wealthy families built grand homes called Berkshire Cottages here, as others would in Lenox and Stockbridge, cementing the region as a resort destination. 

In 1886 William Stanley sent alternating current electricity flowing out of a generating station down Main Street and gave Great Barrington the first electric street lights in the world. But it was another type of light that would be most responsible for shaping the streetscape we’ll see on our walking tour - more than a dozen fires plagued Great Barrington in the 1800s, the most ferocious clearing entire blocks in 1896...

1.
Town Hall
334 Main Street

The town government floated around town for much of the 1800s. One town house burned; meetings were held in a store and on the porch of a church. In 1875 a long-term solution was finally reached with the construction of this red brick town hall. Its design drew heavily on the colonial Georgian style popular a century earlier. The bill for the building and the land came to $50,763. After selling off some town property the tab came to a bit over $35,000. Town offices, courts and a public library occupied the ground floor; upstairs the meeting hall provided space for lectures, recitals and the occasional poultry show. 

2.
Civil War Monument
Town Hall lawn

Vermont-born Truman Howe Bartlett turned out this bronze statue of Victory to honor the sacrifice made by Great Barrington men during the Civil War. The allegorical figure atop the bronze pedestal was said to be a replica recovered from the ruins of Pompeii, Italy. The town appropriated $5,000 towards its construction but when the expense of placing the monument in front of Town Hall shortly after it opened in 1876 soared beyond that the remainder was contributed by John H. Coffing. Coffing began his career as an industrialist in the family iron works and was later a principal in the Monument Mills complex.

3.
Memorial Stone
Town Hall lawn 

On this site in 1764 the first court house was erected in Berkshire County. Ten years later on August 16, 1774 the county court house in Great Barrington was the site of the first open resistance to British judicial rule. Also on this site once stood the original marker to that history. This is a replacement placed in 2005. It is made of granite, more resistant to the ravages of acid rain and the occasional car bumper than the dolomite stone placed here in 1890.

WITH YOUR BACK TO TOWN HALL, TURN RIGHT ON MAIN STREET. 

4.
St. James Episcopal Church
352 Main Street 

The parish dates to 1762 with a small meetinghouse constructed shortly afterwards. This Gothic-style building, the third to serve the church, was constructed in 1857 at a cost of $15,232. Blue dolomite stone from East Mountain was carted into town for its construction. The stained glass windows dating from the late 19th and early 20th centuries have since been restored to their original splendor.

5.
Dwight-Henderson House
Main Street 

Joseph Dwight was native-born in 1703 and went on to practice law after graduating from Harvard College. When not engaged in the law and politics he was a colonel in the local militia and distinguished himself as the commander of the Massachusetts Artillery at the siege and capture of Louisbourg in the French and Indian War. Afterward he returned to the Housatonic Valley and in 1752 then General Dwight married the widow of the Reverend John Sergeant, founder of Stockbridge. He bought this salt-box house, well-preserved for over 250 years, in 1759. Joseph Dwight would die in 1765. An early history of the town described him thusly, “No man in the county in civil life, was more esteemed; and aged people still speak of him with great respect.” 

6.
Searles Castle
389 Main Street 

At the age of 35 Mark Hopkins set out for the California gold fields in 1849 but not to pan for precious metal but to sell goods to miners. By 1855 he was operating a hardware and iron business in Sacramento and in 1861 he was the eldest of four partners who formed the Central Pacific Railroad that was to build half of the Transcontinental Railroad. Hopkins would become one of America’s wealthiest men. And few men so rich were ever so thrifty. But his wife could spend the money. She engineered the construction of a fabulous mansion on San Francisco’s Nob Hill and after Hopkins died in 1878 she made her way back east and in the 1880s constructed a 60,000 square-foot fortress on 61 acres on Main Street. The great home constructed of blue dolomite sported seven turrets and 40 rooms. She hired interior decorator Edward Searles to fill those 40 rooms and a year before it was finished Mary Hopkins married Searles, 22 years her junior. She died in 1891 and most of Mark Hopkins’ money - he never had a will - passed to Edward Searles. He stayed in the castle until 1920 after which the structure was used as a private girls’ school for 30 years, then passed through various owners and was used as a storage area and conference center. From the 1980s until 2007 it housed a school for troubled teens and then was sold for $15 million. 

7.
Taylor Hill
426 Main Street

Celebrated poet William Cullen Bryant had a day job as the town clerk in Great Barrington from the ages 21 to 31, 1815 to 1825. In 1821 he met, courted and eventually married Frances Fairchild in the Dwight House up the street. For a year after his marriage he rented this house for $30, plus another 17 cents a week to pasture his cow, from lawyer George Ives who built it in 1815. In 1826 his brother-in-law Ralph taylor purchased the house and named it Taylor Hill. It has done duty as a funeral home since 1918. 

TURNAND WALK BACK TO TACONIC STREET AND TURN LEFT. TURN RIGHT ON CASTLE STREET. 

8.
Great Barrington Train Station
46 Castle Street

The original Housatonic Railroad was chartered in 1836 running from Connecticut up through Berkshire County. When the line was acquired by the New York, New Haven & Hartford Railroad in 1892 the short-line railroad boasted 175 miles of track with 60 passenger depots. The last passenger train ran on April 30, 1971. This slate-roofed depot was constructed in 1901.

WALK TO THE END OF THE STREET AND LOOK UP THE HILL ON THE OPPOSITE SIDE. 

9.
Russell House
54 Castle Street

In 1830 brothers Asa and John Russell went into partnership in a mercantile enterprise on the corner of Castle Street that grew into the Berkshire Woolen Company. Asa purchased this 1820s house that spans the Federal and Greek Revival periods of American architecture and it served as the family home for two generations. It would become the home to the Children’s Health Program charity that reconfigured the interior for office use. 

TURN RIGHT AND WALK THROUGH THE UNDERPASS BENEATH THE RAILROAD TRACKS TO CASTLE STREET ON THE OTHER SIDE.

10.
Great Barrington Fire Station
20 Castle Street

Fire protection in Great Barrington can be traced to 1854 when a group of nineteen young men who formed the Hope Fire Company and raised enough money to buy a Button hand pumper. That same year, the Great Barrington Fire District was organized to supply the water to the center of town from the East Mountain Reservoir. This firehouse of red brick and granite trim, the company’s fourth, rose from the ashes of the town’s largest fire that burned both sides of Railroad Street and spread to Castle Street at the turn of the 20th century. In 1976 the fire station and apparatus were sold to the Town of Great Barrington and the Hope Company and the Housatonic Hose Company that dates to 1889 were combined into one department. Both remain in existence today as social wings of the Great Barrington Fire Department that has since moved its main headquarters.

11.
Mahaiwe Performing Arts Center
14 Castle Street 

The original Mahaiwe Block that stood here in the 1800s burned to the ground in 1901 and the property was redeveloped into the town’s first theater. The Mahaiwe Theater opened as a live vaudeville venue in 1905 but films came early, beginning in 1912. By the time the first “talkies” arrived in 1927 live performances were a thing of the past and for the next 70 or so years the Mahaiwe (pronounced ‘Ma-Hay-Wee’) was a place to experience a movie, not just watch it. Passionate theater-lovers helped push back plans to convert the movie house into an apartment complex and the Mahaiwe was completely restored in time for its centennial celebration in 2005.

TURN LEFT ON MAIN STREET. TURN LEFT ON RAILROAD STREET.

12.
Railroad Street 

Fire regularly visited the commercial center of town along Railroad Street in the 1800s. Today the block retains a turn-of-the-20th century feel. At the head of the block on the south corner of Main Street is the City Store, three bays wide by nine bays deep. Built of brick in 1853 it was the first commercial block inGreat Barrington and one of the few structures to survive the Great Fire of 1896. The original town train depot was located at the foot of the street which was extended with a hook to Elm Street in 1901. Pioneering Civil Rights activist William Edward Burghardt Du Bois was born in Great Barrington, a place he described as “by a golden river and in the shadow of two great hills...,” in 1868. When he was 11 his family moved into an apartment over a store by the trail station; it is now a parking lot. After attending great Barrington High School Du Bois attended Fisk University in Tennessee and then earned a PHD as the first black to graduate from Harvard University. He entered the national consciousness as a writer and head of the National Association for the Advancement of Colored People in 1910. A marker identifies his birthplace down Church Street on the opposite side of Main Street; The Du Bois Center at Great Barrington is dedicated to his life on South Main Street. 

FOLLOW RAILROAD STREET AS IT BENDS TO THE RIGHT AND CONTINUES TO ELM STREET. TURN RIGHT. TURN LEFT ON MAIN STREET AND STAY ON THE WEST (LEFT) SIDE OF THE STREET.  

13.
U.S. Post Office
222 Main Street

The first mail in the Berkshires was delivered by post rider until the first post office was established at Stockbridge in 1792; the fourth post office in the county came to Great Barrington in 1797. The first post-master was Moses Hopkins and he held the job until his death in 1838. The current Neoclassical post office, fronted by a quartet of imposing Doric columns, was constructed in 1936 as a Depression-era Works Progress Administration project.

CROSS OVER MAIN STREET TO THE EAST SIDE AND TURN RIGHT TO WALK BACK UP MAIN STREET.

14.
St. Peter’s Catholic Church
213 Main Street 

The first Catholic services in Great Barrington were held on the second floor of Town Hall in 1841. The Gothic-inspired stone church welcomed the congregation in 1911.

15.
Mason Library
231 Main Street

Mary A. Mason, widow of Civil War Captain Henry Hobart Mason who was later a New York lawyer and law reporter, provided $50,000 for a new library to replace a clapboard structure that had served the town from this site. The architectural firm of Blanchard & Barnes of New York City were hired to design the Colonial Revival building and when it opened in 1912 it was proclaimed to be “the most beautiful small library building in America.”

16.
First Congregational Church
251 Main Street 

The parish, originally known as the North Parish of Sheffield, was formed by legislative enactment in 1742 and a meeting house erected. The handsome multi-chromatic stone church is the congregation’s fourth, erected after a fire destroyed the previous blue limestone church in 1882. Hartford architect W.C. Brocklesby designed the church and manse which are listed on the National Register of Historic Places. The church is famous for its magnificent organ installed in 1883 by Hilburne Roosevelt Organ Works, America’s most prominent organmaker of the age. The massive instrument uses 3954 pipes and is operated by more than two miles of concealed electric wire. 

17.
 Main Street

A Lenox man, John D. Cushing, put out the first issue of the Berkshire Courier on October 16, 1834. The weekly newspaper sifted through several name and location changes until it landed in this building in 1870 that housed the offices and printing press. A new larger press necessitated moving the office next door to the Marble Block in 1902. After that the building was used as a bakery and when the Great Barrington Savings Bank came in 1916 they added the colonnade of classical fluted columns. The Courier continued to publish until 1993.

CONTINUE ON MAIN STREET UNTIL YOU RETURN TO THE TOUR STARTING POINT AT TOWN HALL.