Stockbridge MA: what to see, where to stay and how to get around
Stockbridge began in the 1730s as a mission town for the Mohican people, and by the end of the 19th century it was where rich New York and Boston families built their summer houses. Norman Rockwell spent the last 25 years of his life here and painted its neighbours into his covers. Everything on this route is within a few kilometres of the Red Lion Inn. The houses and the museum deserve an hour or two each, so pick what you like.
A short history of Stockbridge MA
Stockbridge was founded in 1734 as a mission village for the Mohicans, under the preacher John Sergeant. In the 19th century it became a summer town for wealthy families from Boston and New York, and on the edge of the town the sculptor Daniel Chester French, creator of the Lincoln statue in Washington, built his house and studio. The painter Norman Rockwell lived here from 1953 until his death in 1978, and his 1967 painting of Main Street at Christmas made it a symbol of the American small town. Today the Norman Rockwell Museum is here.
The ten best sights in Stockbridge MA
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1Red Lion Inn
The big white inn on Main Street; sit on the long front porch even if you are not staying
2Main StreetOne short street of white clapboard buildings; it is the street in Rockwell's Christmas painting
3Norman Rockwell MuseumThe largest collection of Rockwell's original paintings, with his studio moved onto the grounds
4NaumkeagA Gilded Age summer house with original furniture and famous gardens; the Blue Steps are the photo
5ChesterwoodThe studio where the seated Lincoln of the Lincoln Memorial was designed
6Mission HouseThe 1739 house of the town's first minister; open in summer only
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7Tanglewood
Summer home of the Boston Symphony; a lawn ticket and a picnic is the local way
8The MountEdith Wharton's own house and gardens, which she designed herself
9Hancock Shaker VillageA whole Shaker village with the famous round stone barn; give it half a day
10ArrowheadHerman Melville's farmhouse, where he wrote Moby-Dick
Scan with your phone camera to open the map there
What is an audio walk?
Tours in Stockbridge MA →A guide in your headphones: open the walk on our site, walk from stop to stop, and at each one your phone tells its story. No guide, no group, and free. This is the first walk in Stockbridge MA:
Free walking tours in Stockbridge MA
Rockwell's Stockbridge
Stockbridge began in the 1730s as a mission town for the Mohican people, and by the end of the 19th century it was where rich New York and Boston families built their summer houses. Norman Rockwell spent the last 25 years of his life here and painted its neighbours into his covers. Everything on this route is within a few kilometres of the Red Lion Inn. The houses and the museum deserve an hour or two each, so pick what you like.
- Red Lion Inn · The inn began as a small tavern in 1773 and burned down in 1896, but its collection of old furniture and china was carried out and saved. Since 1968 it has belonged to the Fitzpatrick family, who founded the Country Curtains business.
- Mission House · The house was built in 1739 for John Sergeant, the first missionary to the Mohicans of Stockbridge, on the hill above the village. In the late 1920s Mabel Choate of Naumkeag had it taken apart and rebuilt on Main Street as a museum.
- Stockbridge Cemetery · In the Sedgwick family plot, known as the Sedgwick Pie, the graves stand in rings around the founder Theodore Sedgwick. Among them lies Elizabeth Freeman, an enslaved woman who sued for her freedom in 1781 with Sedgwick as her lawyer and won. Norman Rockwell is buried in the same cemetery.
- Naumkeag · Stanford White of McKim, Mead & White designed the house in 1885 for Joseph Hodges Choate, a New York lawyer who later became the American ambassador in London. The Blue Steps, a stair of blue fountains between white birches, were added by landscape architect Fletcher Steele in 1938.
- Norman Rockwell Museum · Rockwell moved to Stockbridge in 1953 and lived here until his death in 1978. His studio, a red barn that stood behind his house in town, was moved in one piece to the museum grounds in 1986, with his easel and brushes inside.
- Chesterwood · This was the summer home and studio of Daniel Chester French, the sculptor of the seated Abraham Lincoln in the Lincoln Memorial in Washington. The studio has a railway track in the floor, used to roll large clay models outside to see them in daylight.
Music, Melville and the Shakers
North of Stockbridge the Berkshires turn into a landscape of summer culture. Lenox has Tanglewood and Edith Wharton's house, Pittsfield has Melville's farm, and on its western edge stands a whole Shaker village. The route ends on the summit of Mount Greylock, the highest point in Massachusetts. It is about 50 km from Stockbridge to the summit on country roads.
- Tanglewood · The Boston Symphony Orchestra has played its summer season here since 1937, after a local family gave the estate to the orchestra. The open-sided Shed seats about 5,000, and thousands more listen from the lawn.
- The Mount · Edith Wharton built the house in 1902 and planned it herself, following the rules she had set out in her book The Decoration of Houses. She wrote The House of Mirth here, before leaving for France in 1911.
- Pleasant Valley Wildlife Sanctuary · The Mass Audubon sanctuary lies on the slopes of Lenox Mountain, and its trails run past ponds built by beavers. Walk quietly at dusk and you may see them working.
- Arrowhead · Herman Melville bought the farm in 1850 and wrote Moby-Dick here, in a study with a view north to Mount Greylock. He lived here until 1863, when money troubles sent him back to New York.
- Hancock Shaker Village · The Shakers lived here from the 1790s until 1960, when the last members left and the village became a museum. Their round stone barn of 1826 let one farmer feed the whole herd from the centre.
- Mount Greylock · At 1,064 metres it is the highest point in Massachusetts, crowned by a granite war memorial tower with a light at the top. Henry David Thoreau climbed it in 1844 and spent the night on the summit.
South county: a mountain, a song and a waterfall
South of Stockbridge the Housatonic valley opens towards Great Barrington, a real small town with shops and restaurants. On the way stands the mountain where two great writers first met, and the church that gave America its Thanksgiving song. Further south and west the road ends at the deepest gorge in the state. Count on about 70 km for the whole loop.
- Ice Glen · The narrow ravine is filled with huge moss-covered boulders under old hemlocks, and so little sun reaches the bottom that ice can last in the cracks into summer. It is a 20-minute walk from Main Street over the railway bridge.
- Monument Mountain · On 5 August 1850 a party of writers climbed the mountain, among them Herman Melville and Nathaniel Hawthorne, who met here for the first time. A thunderstorm drove them under a ledge, and the friendship that began there shaped Moby-Dick, which Melville dedicated to Hawthorne.
- Guthrie Center · Alice and Ray Brock lived in this old church, and their Thanksgiving dinner of 1965 ended with Arlo Guthrie arrested in Stockbridge for dumping their rubbish. He told the story in the 18-minute song Alice's Restaurant, and later bought the church himself.
- Great Barrington · In 1886 William Stanley lit shops and offices on Main Street with alternating current, the first such system in America. The civil rights leader W. E. B. Du Bois was born in the town in 1868.
- Bartholomew's Cobble · The cobbles are knolls of marble and quartzite above a bend of the Housatonic, and the lime in the rock feeds an unusual number of ferns and wildflowers. It is a National Natural Landmark, with easy riverside paths.
- Bash Bish Falls · It is the highest single-drop waterfall in Massachusetts, where the brook splits around a boulder before falling into a green pool. The gorge sits right on the New York state line, and the easiest path starts from a car park on the New York side.
Getting to Stockbridge MA and getting around
- Pittsfield Intermodal Center · Pittsfield's station for the daily Amtrak train to Boston and Chicago and regional buses, 25 minutes north
- Massachusetts Turnpike at Lee · The Mass Pike interchange at Lee is ten minutes away; the fast road east to Boston and west to Albany
- Pittsfield Municipal Airport · A small airfield for private planes only; airline flights mean Albany, about an hour away
Cheap eats in Stockbridge MA
The Berkshires eat well but not cheaply: farm cheeses, apple cider, maple syrup and good bakeries, with prices to match the summer visitors from New York and Boston. Stockbridge itself is tiny and has only a couple of places to eat besides the Red Lion Inn, so for a quick lunch it is worth looking to Lee, Lenox and Great Barrington, each about 10 to 15 minutes away. Many places close one or two days a week and shorten their hours in winter.
- Stockbridge General Store · Coffee, sandwiches and snacks on Main Street, about $6-14
- Patisserie Lenox · French pastries and coffee in Lenox village, about $4-10
- Haven Cafe and Bakery · Breakfast and baked goods in Lenox, about $10-18
- Starving Artist Cafe · A café on Lee's Main Street by the turnpike exit, about $6-14
- Rubi's · Coffee and pastries on Great Barrington's Main Street, about $4-10
- Guido's Fresh Marketplace · A big food market in Pittsfield for picnic supplies, about $8-15 for a lunch
Museums in Stockbridge MA
- Norman Rockwell Museum · The biggest collection of his original work; allow two hours
- Chesterwood · Sculptor's studio, house and woodland paths with sculpture
- Naumkeag · House tour plus the gardens; the gardens alone are worth it
- Mission House · A small colonial house on Main Street, summer only
- Arrowhead · Melville's farmhouse and study, 25 minutes north
- Clark Art Institute · Renoirs and other Impressionists in Williamstown, an hour north; a full morning
Nature and day trips near Stockbridge MA
- Ice Glen · A cool boulder ravine from Main Street; scrambling over rocks
- Laura's Tower · Lookout tower above town, a short climb through the woods
- Monument Mountain · Quartzite ridge walk, two to three hours
- Bash Bish Falls · The state's highest single-drop waterfall; steep path
- Mount Greylock · Drive to the summit of Massachusetts in summer and autumn
- Bartholomew's Cobble · Easy riverside paths among ferns and wildflowers
Things to do in Stockbridge MA with kids
- Hancock Shaker Village · Farm animals, the round barn and craft demonstrations
- Berkshire Museum · Natural history, an aquarium and art under one roof in Pittsfield
- Pleasant Valley Wildlife Sanctuary · Beaver ponds and easy trails; dusk is best
- Berkshire Botanical Garden · Small gardens with lawns and paths for an easy hour
- Stockbridge Bowl · A lake for a picnic and a look at the water
Where to eat in Stockbridge MA
- Red Lion Inn · New England dinner in the main dining room, or a pub meal in the Widow Bingham's Tavern
- Shaker Mill Tavern · A relaxed tavern in West Stockbridge, 10 minutes away
- Salmon Run Fish House · Seafood on Lee's Main Street
- 51 Park Restaurant & Tavern · Restaurant and bar in the centre of Lee
- Baba Louie's · Sourdough-crust pizza in Great Barrington
- 20 Railroad Public House · A pub on Railroad Street, Great Barrington
Frequently asked questions about Stockbridge MA
What is there to see in Stockbridge MA?
The top sights in Stockbridge MA are Red Lion Inn, Main Street and Norman Rockwell Museum. The full list on this page has 10 sights, each with a photo and a short note.
How many days do you need in Stockbridge MA?
Three to four days are enough to see the best of Stockbridge MA without rushing, including at least one walking tour.
Is there a free walking tour in Stockbridge MA?
Yes. sleepntrip has 3 free audio walks in Stockbridge MA, with no guide and no group: your phone tells the story at every stop. The first one: Rockwell's Stockbridge.
How do you get to Stockbridge MA and get around?
The main ways are Pittsfield Intermodal Center, Massachusetts Turnpike at Lee and Pittsfield Municipal Airport. Full details are in the transport section on this page.
Where to stay in Stockbridge MA, and for how much?
sleepntrip shows only rooms in Stockbridge MA that meet nine conditions: a good location, high guest scores, cleanliness, and a price of up to $80 a night for two. Pick your dates and see what is free.
Looking for a hotel in Stockbridge MA for your dates?
Only rooms that meet nine conditions, up to $80 a night.