Aaron’s guidebook
Sightseeing
Pontoosuc Lake
Kayaks, speed boat and pontoon rentals available with booking.
Local artist Normal Rockwell's museum and studio is open. year round.
344 locals recommend
Norman Rockwell Museum
9 Glendale RdLocal artist Normal Rockwell's museum and studio is open. year round.
Spend the day at Mass Moca and explore Northern Berkshire County. Restaurants and a microbrewery available on the property.
382 locals recommend
MASS MoCA
1040 Mass MoCA WaySpend the day at Mass Moca and explore Northern Berkshire County. Restaurants and a microbrewery available on the property.
Spend the summer enjoying the Boston Symphony, Boston Pops and popular artists at this historic, beautiful outdoor venue. Bring a picnic, buy food there, walk the grounds and enjoy the show from in the shed or under the stars.
398 locals recommend
Tanglewood
Spend the summer enjoying the Boston Symphony, Boston Pops and popular artists at this historic, beautiful outdoor venue. Bring a picnic, buy food there, walk the grounds and enjoy the show from in the shed or under the stars.
Jimmy Peak offers outdoor fun year round. Skiing in the winter and an outdoor adventure park the rest of the year.
200 locals recommend
Jiminy Peak
37 Corey RdJimmy Peak offers outdoor fun year round. Skiing in the winter and an outdoor adventure park the rest of the year.
Skiing and tubing in the winter. Outdoor adventure and water park available the summer months.
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrSkiing and tubing in the winter. Outdoor adventure and water park available the summer months.
Bartlett's Orchard
575 Swamp RdPick your own apples and enjoy a warm, cider donut.
Enjoy apple picking in the fall and wine and donuts all. year long. They have trails available for hiking and snowshoeing.
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdEnjoy apple picking in the fall and wine and donuts all. year long. They have trails available for hiking and snowshoeing.
There are many local theaters in the Berkshires to choose from. Each offering something different and enticing for it’s guests.
61 locals recommend
Berkshire Theatre Group
6 East StThere are many local theaters in the Berkshires to choose from. Each offering something different and enticing for it’s guests.
Enjoy the culture of the Berkshires with this breathtaking outdoor dance experience at Jacob's Pillow.
257 locals recommend
Jacob's Pillow
358 George Carter RdEnjoy the culture of the Berkshires with this breathtaking outdoor dance experience at Jacob's Pillow.
Year round activities to enjoy. Explore the grounds or take in a show.
167 locals recommend
The Mount, Edith Wharton's Home
2 Plunkett StYear round activities to enjoy. Explore the grounds or take in a show.
One of the many historic properties available to tour in the Berkshires. They have seasonal events available as well as gorgeous gardens to explore.
109 locals recommend
Naumkeag
5 Prospect Hill RdOne of the many historic properties available to tour in the Berkshires. They have seasonal events available as well as gorgeous gardens to explore.
Laura Lookout Tower
Beautiful hiking trail.
Onota Lake
Lakeway DriveEasy access public beaches and boat ramp.
Ski Butternut
380 State RdWonderful ski mountain located in South County.
Located just over the NY border. Day and evening skiing available.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdLocated just over the NY border. Day and evening skiing available.
Catamount offers year-round family fun. Explore their aerial park for an adventure-filled day.
56 locals recommend
Catamount Aerial Adventure Park
17 Nicholson RdCatamount offers year-round family fun. Explore their aerial park for an adventure-filled day.
Have a fun-filled day full of adventure and amazing views at Ramblewild.
76 locals recommend
Ramblewild Adventure Park
110 Brodie Mountain RdHave a fun-filled day full of adventure and amazing views at Ramblewild.
Food scene
Wonderful local winery. Indoor and outdoor seating. They often have live music and food trucks for your enjoyment.
29 locals recommend
Balderdash Cellars
81 State RdWonderful local winery. Indoor and outdoor seating. They often have live music and food trucks for your enjoyment.
Great food, extensive beer menu. There wings are a must try!
39 locals recommend
Olde Forge Restaurant
125 N Main StGreat food, extensive beer menu. There wings are a must try!
Frankie's
80 Main StFabulous Italian food, indoor and outdoor seating. Nice wine selection.
Otto's Kitchen & Comfort
95 East StFun, delicious local eatery. Creative menu.
Betty's Pizza Shack
26 Housatonic StA fun, fabulous surf themed pizza shop.
Wandering Star Craft Brewery
11 Gifford StLocal brewery, craft beers, fun & relaxed atmosphere.
Located in the quaint, historic town of Stockbridge. 3 choices for your dining pleasure. Live music in the Lion's Den. Eat at the bar or enjoy a full dining experience in their historic dining room.
117 locals recommend
The Red Lion Inn
30 Main StLocated in the quaint, historic town of Stockbridge. 3 choices for your dining pleasure. Live music in the Lion's Den. Eat at the bar or enjoy a full dining experience in their historic dining room.
Worth the short drive down to Sheffield to experience this local brewery.
31 locals recommend
Big Elm Brewing
65 Silver StWorth the short drive down to Sheffield to experience this local brewery.
Berkshire Mountain Distillers
356 S Main StTastings available.
A trip to the Berkshires isn't complete without exploring Great Barrington and enjoying a cool treat from Soco Creamery.
45 locals recommend
Soco Creamery
5 Railroad StA trip to the Berkshires isn't complete without exploring Great Barrington and enjoying a cool treat from Soco Creamery.
Jae's
1032 South StreetWonderful sushi and other Asian-inspired food. Thier pad thai is AMAZING.