Parks & Nature
Beautiful gushing waterfalls that one can bask in; swimming hole; picnic area; trails
33 locals recommend
Umpachene Falls Park
Umpachene Falls RoadBeautiful gushing waterfalls that one can bask in; swimming hole; picnic area; trails
Beautiful York Lake; Beach area; Swimming; Nature trails; Picnic areas; Fishing & boating.
Sandisfield State Forest
Beautiful York Lake; Beach area; Swimming; Nature trails; Picnic areas; Fishing & boating.
Breathtaking waterfalls and streams; nature/hiking trails.
281 locals recommend
Bash Bish Falls State Park
Falls RoadBreathtaking waterfalls and streams; nature/hiking trails.
Drinks & Nightlife
Alta
34 Church StStylish wine bar. Lunch, dinner & small bites.
Intimate setting to hear great bands and vocalists while enjoying interesting food, great cocktails and wines.
172 locals recommend
Helsinki Hudson
405 Columbia StIntimate setting to hear great bands and vocalists while enjoying interesting food, great cocktails and wines.
Small, intimate tavern at the renowned Red Lion Inn. Tucked away from the bustling Inn, a great place for hearty fare, beers, cocktails and cozy fireside dining in the winter.
28 locals recommend
Lion's Den
30 Main StSmall, intimate tavern at the renowned Red Lion Inn. Tucked away from the bustling Inn, a great place for hearty fare, beers, cocktails and cozy fireside dining in the winter.
Food Scene
Terrific Tuscan style restaurant serving dinner only. Try the Berkshire pork or the homemade pastas.
39 locals recommend
Allium Restaurant + Bar
42/44 Railroad StTerrific Tuscan style restaurant serving dinner only. Try the Berkshire pork or the homemade pastas.
Authentic Mexican cuisine serving lunch and dinner. Outdoor dining on wrap around porch in summer.
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge RdAuthentic Mexican cuisine serving lunch and dinner. Outdoor dining on wrap around porch in summer.
The best pizza anywhere. Sourdough thin crust pizzas with a variety of fresh toppings. Popular for lunch and dinner. Take out also available.
121 locals recommend
Baba Louie's Sourdough Pizza
42/44 Railroad StThe best pizza anywhere. Sourdough thin crust pizzas with a variety of fresh toppings. Popular for lunch and dinner. Take out also available.
Great breakfasts and lunch. Dinner now served in the Great Barrington restaurant. Homemade baked goods, outstanding soups, salads, wraps & sandwiches.
17 locals recommend
Marketplace Kitchen Table
240 Stockbridge RdGreat breakfasts and lunch. Dinner now served in the Great Barrington restaurant. Homemade baked goods, outstanding soups, salads, wraps & sandwiches.
Trendy coffee house serving hot and cold beverages, espresso, latte and a great cup of joe. Relaxing place to hang, work on laptop or meet up with friends.
65 locals recommend
Fuel Bistro/ Coffee Shop
293 Main StTrendy coffee house serving hot and cold beverages, espresso, latte and a great cup of joe. Relaxing place to hang, work on laptop or meet up with friends.
A Berkshire County institution, Guido's Fresh Marketplace offers outstanding produce, meats, seafood, fresh pasta, freshly baked breads and deserts, cheeses from all over and an excellent, well-priced wine and spirits shop. The ultimate "foodie" experience.
248 locals recommend
Guido's Fresh Marketplace
760 S Main StA Berkshire County institution, Guido's Fresh Marketplace offers outstanding produce, meats, seafood, fresh pasta, freshly baked breads and deserts, cheeses from all over and an excellent, well-priced wine and spirits shop. The ultimate "foodie" experience.
One of the most extensive selections of artisanal cheeses, cured meats and pates. A separate bakery/cafe offers delicious coffees and espresso drinks, baked goods and lunch items.
52 locals recommend
Rubiner's Cheesemongers
264 Main StOne of the most extensive selections of artisanal cheeses, cured meats and pates. A separate bakery/cafe offers delicious coffees and espresso drinks, baked goods and lunch items.
A festive and nostalgic candy shop that offers an amazing selection of chocolates, licorice, ice cream, lollipops and packaged candy classics.
14 locals recommend
Robin’s Candy
288 Main StA festive and nostalgic candy shop that offers an amazing selection of chocolates, licorice, ice cream, lollipops and packaged candy classics.
A great place for home grown fruits and veggies, baked goods and amazing fruit pies. Extensive selection of holiday trees, wreaths, pumpkins and gourds, fresh floral arrangements and garden annuals.
27 locals recommend
Taft Farms
119 Park StA great place for home grown fruits and veggies, baked goods and amazing fruit pies. Extensive selection of holiday trees, wreaths, pumpkins and gourds, fresh floral arrangements and garden annuals.
Sightseeing
Norman Rockwell's famous streetscape come to life. Nice shops, eateries, holiday festivals and home of the famous Red Lion Inn.
9 locals recommend
Main Street
317 Main StNorman Rockwell's famous streetscape come to life. Nice shops, eateries, holiday festivals and home of the famous Red Lion Inn.
Beautiful drive to the mountain with scenic lookouts along the way. Herman Melville was inspired by the view of the mountain from his home, "Arrowhead," where he wrote Moby Dick.
213 locals recommend
Mount Greylock
Beautiful drive to the mountain with scenic lookouts along the way. Herman Melville was inspired by the view of the mountain from his home, "Arrowhead," where he wrote Moby Dick.
Arts & Culture
Summer home of the Boston Symphony Orchestra, offering a live concert performances ranging from classical, to jazz to iconic film scores. Enjoy a summer evening and picnic supper on the great lawn while listening to some of the most revered musical artists and orchestras in the world.
394 locals recommend
Tanglewood
Summer home of the Boston Symphony Orchestra, offering a live concert performances ranging from classical, to jazz to iconic film scores. Enjoy a summer evening and picnic supper on the great lawn while listening to some of the most revered musical artists and orchestras in the world.