Food Scene
Main Street Cafe
40 Main StRight in the middle of Stockbridge. Great for breakfast and lunch.
Part of the historic Red Lion Inn. Serves dinner and drinks and has live music several nights a week.
28 locals recommend
Lion's Den
30 Main StPart of the historic Red Lion Inn. Serves dinner and drinks and has live music several nights a week.
Great local bakery. Wonderful sourdough bread and croissants and coffee. Terrific "take and bake" pizza with crispy crust and fresh toppings.
64 locals recommend
Berkshire Mountain Bakery Inc
367 Park StGreat local bakery. Wonderful sourdough bread and croissants and coffee. Terrific "take and bake" pizza with crispy crust and fresh toppings.
History, Art and Culture
Stockbridge Town Hall
If you're interested in Norman Rockwell, the Town Hall has a wonderful collection of photographs that Norman Rockwell used for his illustrations, side by side with the illustrations. The models in the photographs were town residents, some of whom still live in Stockbridge (but you won't recognize them, because they were kids then). The Town Hall is open weekdays and there are very clean, accessible public restrooms on the ground floor.
Norman Rockwell was one of America's most well known illustrators, famous for magazine covers depicting American Life in the 1950s and 1960s, and for the paintings of "The Four Freedoms" The museum also has other illustrators on special exhibit.
343 locals recommend
Norman Rockwell Museum
9 Glendale RdNorman Rockwell was one of America's most well known illustrators, famous for magazine covers depicting American Life in the 1950s and 1960s, and for the paintings of "The Four Freedoms" The museum also has other illustrators on special exhibit.
Chesterwood is the summer home and studio of Daniel Chester French, the artist/scuptor most well known for his sculpture of Abraham Lincoln at the Lincoln Memorial in Washington, DC. To scale mock-ups of the Lincoln Memorial sculpture are in the studio, plus other sculptures he produced.
63 locals recommend
Chesterwood
4 Williamsville RdChesterwood is the summer home and studio of Daniel Chester French, the artist/scuptor most well known for his sculpture of Abraham Lincoln at the Lincoln Memorial in Washington, DC. To scale mock-ups of the Lincoln Memorial sculpture are in the studio, plus other sculptures he produced.
Hiking, Parks and Nature
Berkshire Botanical Gardens
A lovely, 15 acre Botanical Garden located on Rte. 102 just a couple of miles outside of Stockbridge.
Challenging hiking up Monument Mountain. At the top, you'll be looking out over Stockbridge and Great Barrington. Busy on the weekends in good weather Spring, Summer and Fall.
112 locals recommend
Monument Mountain Reservation
Challenging hiking up Monument Mountain. At the top, you'll be looking out over Stockbridge and Great Barrington. Busy on the weekends in good weather Spring, Summer and Fall.
Parts of the Appalachian trail in Massachusetts are accessible from Monterey, West Stockbridge, Rte. 7 in Stockbridge (connecting trail) Rte. 20 in Lee. If you're through-hiking, none of the trail heads are really close to the towns, but if you're day hiking, all of the trail heads have good parking.
9 locals recommend
Appalachian trail
Parts of the Appalachian trail in Massachusetts are accessible from Monterey, West Stockbridge, Rte. 7 in Stockbridge (connecting trail) Rte. 20 in Lee. If you're through-hiking, none of the trail heads are really close to the towns, but if you're day hiking, all of the trail heads have good parking.
Shopping and Essentials
Premium Outlets
The Premium Outlets are located on Rte. 20 East and have a good selection of women's clothing shops, footwear, outdoor wear, cosmetics, candles and toiletries. You can check out their website to see the full list of shops.
Big Y World Class Market
10 Pleasant St