Berkshires Guidebook
Coffee / Breakfast / Lunch
French-inspired cafe & patisserie serving coffee, tea, pastries and more.
15 locals recommend
The Lost Lamb
31 Main StFrench-inspired cafe & patisserie serving coffee, tea, pastries and more.
House-roasted coffee & organic simple fare served in a renovated train station cafe. Also serve lunch.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StHouse-roasted coffee & organic simple fare served in a renovated train station cafe. Also serve lunch.
Relaxed, locally focused American eatery for crepes, panini & coffee, plus gluten-free & vegan fare.
40 locals recommend
Starving Artist Creperie and Cafe
40 Main StRelaxed, locally focused American eatery for crepes, panini & coffee, plus gluten-free & vegan fare.
On A Roll Cafe And Catering
55 Pittsfield RdCasual breakfast and sandwich spot
Casual breakfast, sandwiches and salads, a great option for taking food to go for a picnic.
17 locals recommend
Marketplace Kitchen Table
240 Stockbridge RdCasual breakfast, sandwiches and salads, a great option for taking food to go for a picnic.
FARM COUNTRY SOUP
389 Stockbridge RdFarm fresh & organic cafe, bakery and lunch spot offering rotating seasonal menu.
Espresso drinks & bistro fare doled out in a lofty brick-lined space with a full bar & cool vibe.
65 locals recommend
Fuel Bistro/ Coffee Shop
293 Main StEspresso drinks & bistro fare doled out in a lofty brick-lined space with a full bar & cool vibe.
Upscale American breakfast & lunch cafe with an in-house bakery & patio seating.
67 locals recommend
Haven
8 Franklin StUpscale American breakfast & lunch cafe with an in-house bakery & patio seating.
A cute locally-owned coffee shop with coffee, tea and hot chocolate, snacks, newspapers, and books. Seating is limited
8 locals recommend
Stockbridge Town Park
A cute locally-owned coffee shop with coffee, tea and hot chocolate, snacks, newspapers, and books. Seating is limited
Lunch / Dinner
Buzzing eatery/wine bar offering a Mediterranean menu & a covered porch for outdoor dining. Also serves dinner
53 locals recommend
Alta
34 Church StBuzzing eatery/wine bar offering a Mediterranean menu & a covered porch for outdoor dining. Also serves dinner
Hip neighborhood hangout spot serving Neapolitan style pizza made in house as well as an assortment of appetizers, salads and drinks.
20 locals recommend
Pizzeria Boema
84 Main StHip neighborhood hangout spot serving Neapolitan style pizza made in house as well as an assortment of appetizers, salads and drinks.
Wine & beer bar offering bites such as pizza, cheese & charcuterie in intimate surrounds.
50 locals recommend
Brava
65 Church StWine & beer bar offering bites such as pizza, cheese & charcuterie in intimate surrounds.
Special-occasion restaurant offering New American dishes in a bustling, rustic-chic atmosphere.
55 locals recommend
Cafe Adam, Bar and Restaurant
420 Stockbridge RdSpecial-occasion restaurant offering New American dishes in a bustling, rustic-chic atmosphere.
Authentic Mexican eatery known for its mole & margaritas, with patio seating & live music on weekends.
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge RdAuthentic Mexican eatery known for its mole & margaritas, with patio seating & live music on weekends.
Elevated, area-sourced American fare & cocktails served in a charming house with a hip, rustic feel.
203 locals recommend
The Prairie Whale
178 Main StElevated, area-sourced American fare & cocktails served in a charming house with a hip, rustic feel.
Seasonal Pub fare sourced from local farms in a historic setting. Classic 1800's mahogany bar, 10 taps of craft beer with classic and modern cocktails.
15 locals recommend
20 Railroad Public House
20 Railroad StSeasonal Pub fare sourced from local farms in a historic setting. Classic 1800's mahogany bar, 10 taps of craft beer with classic and modern cocktails.
Cantina 229
229 Hartsville-New Marlborough RdAgaves Mexican Grill
389 Stockbridge RdSTEAM Noodle Cafe
286 Main StDistrict Kitchen & Bar
40 West StMethuselah
391 North StreetSightseeing
Berkshire Botanical Garden
5 W Stockbridge RdNorman Rockwell Museum
9 Glendale RdChesterwood
4 Williamsville RdNaumkeag
5 Prospect Hill RdThe Mount, Edith Wharton's Home
2 Plunkett StHancock Shaker Village
1843 W Housatonic StMASS MoCA
1040 Mass MoCA WayThe Clark Art Institute
225 South StMission House
19 Main StEntertainment
Tanglewood
Shakespeare & Company
70 Kemble StBerkshire Theatre Group
6 East StMarkets / Convenience / Pharmacies
Nejaime's Wine Cellar
3 Elm StElm Street Market and Tiffany's Cafe'
4 Elm StLoeb's Foodtown of Lenox
42 Main StNejaime's Wine Cellars
60 Main StCVS
481 Pittsfield RdMarket 32
Big Y World Class Market
10 Pleasant StHair / Nails / Spa
Seven Salon Spa
7 South StCanyon Ranch Lenox
165 Kemble StOutdoor Activities
Butternut Basin
Catamount Mountain Ski Resort
78 Catamount RdJiminy Peak
37 Corey RdRetail that offers bikes, kayaks, SUPs, footwear, outdoor clothing and camping gear. They also rent bikes, kayaks, snowshoes and cross country skis.
32 locals recommend
Arcadian Shop
91 Pittsfield RdRetail that offers bikes, kayaks, SUPs, footwear, outdoor clothing and camping gear. They also rent bikes, kayaks, snowshoes and cross country skis.
Greenock Country Club
220 W Park StBerkshire Bike and Board
29 State RdMonument Mountain Reservation
Olivia's Overlook
Hiking TrailsNice walk in the woods with a beautiful waterfall view.
17 locals recommend
Stevens Glen Trail Head Richmond, MA
Lenox RoadNice walk in the woods with a beautiful waterfall view.
Kennedy Park
275 Main StTallest mountain in the state with lots of different trails and the option to drive to the top. In warmer months there is a nice restaurant at the top as well.
213 locals recommend
Mount Greylock
Tallest mountain in the state with lots of different trails and the option to drive to the top. In warmer months there is a nice restaurant at the top as well.
Laura Lookout Tower
Nice quick hike located just outside of downtown Stockbridge.
Notchview | The Trustees of Reservations
83 Old Rte 9