Stockbridge is the second oldest town in the Berkshires, after Sheffield, established in 1834 as a mission for the Mahican Indian tribe. Their missionary was a Yale reverend named John Sergeant and under his guidance “Indian Town” was a great success and Stockbridge, named for the town in Hampshire, England from which the mission hoped to elicit funds,  was incorporated as a town in 1739. Unfortunately Sergeant would live only a decade longer and relations with the Stockbridge Indians deteriorated rapidly. By 1785 their land was sold and the impoverished tribe was led out of the Berkshires - by a son of John Sergeant - to Oneida County, New York where they would gain some notoriety through the writings of James Fenimore Cooper.

The town was little noticed for its first 100 years until the railroad arrived in 1850. But unlike other towns where the Iron Horse brought industry and commerce, to Stockbridge it brought wealthy New Yorkers looking to escape the stale summer air. They built impressive “Berkshire cottages” around town and in America’s Gilded Age the town gained a reputation as the “inland Newport.” In 1853 America’s first village beautification organization, the Laurel Hill Association was formed and continues to this day.

The town gained a reputation as a mecca for writers and artists and it turned out that it would be a magazine illustrator would ingrain Stockbridge into the national psyche. Norman Rockwell spent the final 25 years of his life in Stockbridge, using the downtown scenes for his cover paintings in the Saturday Evening Post and others. And ever since the town has taken pains to insure that those indelible images are not going to go away anytime soon.

Our walking tour will begin off Stockbridge’s busy Main Street and down by the meandering Housatonic River where there is a small park and space for cars and we’ll head up into the town to see why Rockwell once declared, “Stockbridge is the best of America, the best of New England”... 


Cat & Dog Fountain
South Street at Main Street

This small fountain in a traffic island at the head of South Street has been a town landmark since 1862.


Merwin House
14 Main Street 

Francis and Clarissa Dresser built the beginnings of this Federal-style brick house in 1825. It was sold out of the family in 1875 to well-to-do William and Elizabeth Doane from New York as a summer retreat. They added a Shingle-style ell addition and otherwise upgraded the property over the years of their ownership. William died in 1923 and Elizabeth passed away in 1932 and the house passed to their daughter Vipont who moved in with her third husband, New York stockbroker Edward Payson Merwin. He lived only a few more years and Vipont Merwin lived out the final thirty years of her life here. She willed the house to the public for a museum “as an example of an American culture which is fast becoming extinct.” 

Town Hall
6 Main Street on Village Green

This Neoclassical Greek Temple fronted by a quartet of fluted Doric columns handled town functions for many years.

First Congregational Church of Stockbridge
4 Main Street on Village Green 

The church was formally organized in October 1734 when a young tutor from Yale named John Sergeant was sent to preach to the Muh-He-Kun-Ne-Ok (Mohican) people of the Berkshire Hills. Sergeant was quite successful in his mission; in the first year 40 Mohicans, including two chiefs, were baptized. After his death in 1749, Sergeant was followed by fiery preacher Jonathan Edwards who continued the work with the Mohican people while writing his masterpiece, Freedom Of Will, which remains one of the greatest works in american theology. This is the third building for the church, erected in brick in 1824.

Children’s Chime Tower
Village Green

The tower was built in contrasting stone by David Dudley Field to honor his grandchildren. It was dedicated in 1878 and the bells in the 75-foot tower are rung at 5:30 every evening from “apple blossom time till the first frost on the pumpkins.” Field was the oldest of the four sons of the Reverend David Dudley Field, a well-known American clergyman and author, who became one of America’s foremost lawyers and law reformers. The location of the tower is on the spot of the first Stockbridge meetinghouse from 1734. 


Stockbridge Cemetery
Main Street 

This cemetery was founded in the early 1800s around the ancestral family plot of the Sedgwicks, one of the town’s early influential families. When Theodore Sedgwick died in 1813 after a career that included a stint as a justice of the Massachusetts Supreme Judicial Court he was laid to rest here. Around him would be placed the graves of family members, in-laws, servants, and family pets, in concentric circles around patriarch Theodore, grouped by familial affiliation, and placed with their feet toward the center. The arrangement came to be known as the Sedgwick Pie, said to have been conceived so that on the Judgment Day, when the dead are raised, the Sedgwicks will only have to look at other Sedgwicks. Other notables interred here are Cyrus Field, who was the driving force behind the laying of the first trans-Atlantic cable and Norman Rockwell, tucked between his second and third wives, Mary and Molly. 

Mission House
19 Main Street at Sergeant Street

The Reverend John Sergeant came to live among the Stockbridge Mohican Indians in the 1730s, building a simple cabin while he attended to his ministry. Sergeant married Abigail Williams in 1739 and a couple years later he was able to construct this spacious clapboard house on nearby Prospect Hill. In the 1920s the house, a National Historic Landmark, was disassembled, moved, and restored at this location. About that time the grounds were transformed into a replica Colonial garden by famed landscape architect Fletcher Steele with circular brick paths hugged by a cypress fence.

The Austen Riggs Center
25 Main Street

It was while recovering from a bout of tuberculosis in his summer home here that AustenFox Riggs home in 1907 when he became in the study of the mind and health that was just beginning to take hold in the medical community. He developed his own system of treatment based on talk therapy combined with a structured routine of daily activities that emphasized a balance between work, play, rest, and exercise. He founded the “Stockbridge Institute for the Psychoneuroses,” renamed “The Austen Riggs Foundation” in 1919, that has been a fixture on Main Street for over a century. The campus includes several historical buildings including a cottage built in 1772 by Timothy Edwards, a Revolutionary War colonel, and the son of Jonathan Edwards, the second minister of the Stockbridge Congregational Church. The Elms Cottage was the site where the first trans-Atlantic cable message was successfully received from Europe by Stockbridge native Cyrus W. Field. The sprawling white brick Colonial Revival building fronting Main Street was designed by one of America’s most sophisticated architectural firms, Delano & Aldrich. William Adams Delano and Chester Holmes Aldrich met in the late 1890s and partnered in 1903. That first year they secured commissions from the Rockefeller, Stokes and Winthrop families as they went on to design townhouses, country houses, clubs and banks, often in the neo-Georgian and Federal styles, combining brick and limestone, which became their trademark. 

War of the Rebellion Monument
Main Street and Pine Street 

This brownstone obelisk surmounted by a bronze eagle sculpture was dedicated in October 1866, one of the earliest memorials erected to honor Civil War dead. More than 3,000 people attended its dedication. The front features an ornate carving of two flags, crossed swords, a wreath and a soldier’s haversack. Important battles and name of soldiers lost adorn the monument that is fronted by a small cannon.  

St. Paul’s Episcopal Church
29 Main Street

The Episcopalian church in Stockbridge was established in 1834 and for its first 50 years services were held in a wooden Gothic Revival church. The building was razed in favor of the current sanctuary of South Berkshire limestone. The Norman design was provided by Charles Follen McKim, the founding partner in the firm of McKim, Mead & White, which set the standard for architectural taste in the United States between 1879 and 1909. This was McKim’s first church. John La Farge created the Chancel window, a depiction of St. Paul, and the windows flanking the font in the baptistry are by Louis Comfort Tiffany. The statue on the porch, The Spirit of Life, is by the celebrated Daniel Chester French, best remembered for the Lincoln Memorial. The sculptor made his home in West Stockbridge at his Chesterwood estate.

Red Lion Inn
30 Main Street 

On the long colonial road between Boston and Albany in 1773 Anna and Silas Bingham set up a small store in Stockbridge that would soon become a much-welcome rest stop for weary travelers who learned to look for the sign of the red lion. From the fires in the Red Lion Inn sprouted the seeds of Shays Rebellion in 1786-87 that helped forge the power of the new national government in the face of armed protest. In its original incarnation the Red Lion Inn featured bar rooms on the first floor and eight bedrooms and a ballroom upstairs. Through the 1800s the hostelry went through many owners and by 1884 could accommodate over 100 guests. A fire that erupted in the pastry kitchen leveled the Inn in 1896 but it was restored to its former glory in just eight months, albeit under a new red lion shield. The guestbook features five U.S. presidents: Grover Cleveland, William McKinley, Theodore Roosevelt, Calvin Coolidge, and Franklin Roosevelt.

Berkshire Bank
32 Main Street

This was the home of the Housatonic Bank that was incorporated in 1825 with a capitalization of $100,000. The builders didn’t go far for the materials needed to construct the bank - the bricks were fired from clay scraped out of the Housatonic River and the marble for the trim was quarried in West Stockbridge.

Old Town Hall
34 Main Street

This picturesque little red brick and terra cotta building with stepped gables and a rear tower was constructed in 1884 for use as town offices. The government has since left the Queen Anne gem for retail use.

The Mews-”Alice’s Restaurant” Site
40 Main Street 

Down this alley in 1965 was the Back Room Rest, a restaurant owned by Alice M. Brock. That Thanksgiving an 18-year old Arlo Guthrie was arrested for littering while trying to dispose of some of Alice’s garbage after finding the town dump closed for the holiday. That incident became the basis for the iconic 18-minute, 34-second Alice’s Restaurant song on Guthrie’s debut album of the same name and a 1969 movie. Alice Brock only owned the restaurant for about a year and it has operated under various names and figurations in the passing years.

Seven Arts
44 Main Street 

Jason Braman ran a general store out of this 1892 building for many years. Braman posed as the town clerk in Norman Rockwell’s Saturday Evening Post Cover, The Marriage License. The setting for the painting was the interior of the Town Hall down the street.

Stockbridge Library
46 Main Street 

Books were being lent around Stockbridge as early as 1789 when 25 townsfolk formed the Berkshire Republican Library. There was not a library building until 1861, however, when Nathan Jackson of Tyringham, who had been schooled at Stockbridge Academy, offered $2,000 for the purpose. The gift came with a catch - the town had to match the sum. No problem. More than 400 people donated books and raised another $2,500 for the new Stockbridge Library Association. The corner lot at Elm and Main streets was donated by a local shopkeeper with the promise that the new building wouldn’t block her view of Main Street and J.Z. Goodrich constructed the stone building at his own expense. By the summer of 1864 the Stockbridge Social Library opened with 3,000 books. It was commonly called the Jackson Library but Nathan Jackson never saw the fulfillment of his vision - he died a year earlier. A 1930s expansion and remodeling brought the handsome Colonial Revival appearance.

Watering Trough
Main Street at Elm Street 

It has been many a year since a thirsty horse availed itself of the opportunity for a cool drink from this water station in the center of busy Main Street. The trough was installed in 1881 with no pretensions - it bears the messages of its purpose: “Utility is preferable to grandeur” and “Merciful man is kind to his beast.”

Town Offices/Plain School
Main Street

Now home to town offices after a nearly $7 million renovation, this Colonial Revival building was the former Stockbridge Plain School and shared with the former Williams High School. The bust in the niche over the entrance is a nod to the town’s founding as a mission for the Stockbridge Indians.


Elm Street Market
4 Elm Street

Another Norman Rockwell inspiration - the old-fashioned soda counter here wound up in After the Prom

Hose House No. 1
10 Elm Street 

The wooden frame red-and-white fire station dates to 1862. It was the subject of one of Norman Rockwell’s works entitled The New American LaFrance is here! The illustration was part of a series of advertisements for the American LaFrance Fire Engine Co. Although Hose House No. 1 was in use until the 1950s it could never accommodate the American LaFrance pumper depicted in the painting. The fire station was purchased by the Red Lion Inn in 1974 and now serves as their most popular guesthouse.  

St. Joseph Church
11 Elm Street 

This church had its beginnings on this corner in 1862 as a mission church. St. Joseph’s became a parish church in 1922. 


For additional touring... 

To take one of the most unique nature walks in the Berkshires, walk out of the parking lot along Park Street (the Housatonic River will be on your right). At the end of the street cross the river on the footbridge. On the other side turn right to pick up the Ice Glen Trail. Nathaniel Hawthorne called the Ice Glen, a cleft in the rocks between Bear and Little Mountains, “the most curious fissure in all Berkshire.” It is a ravine without a stream - all the water around Ice Glen flows on a south-north axis while the gorge is aligned east to west. In fact, the dry Glen, stuffed with stacked boulders and draped with hemlocks, was once a glacial lake. Tucked away from the sun’s rays, the season’s last snow clings here, hence its name. The entire trail is less than a mile long.