Jessica's Guidebook
Fun for kids (and the young at heart)!
Hancock Shaker Village
1843 W Housatonic StBerkshire Scenic Railway Museum
10 Willow Creek RdBerkshire Museum
39 South StIoka Valley Farm
3475 Hancock RoadFarm animals
Bartlett's Orchard
575 Swamp RdTake a tour and learn about why some maple syrup is dark and some is light... Which is rarer... And the importance of weather!
Mill Brook Sugarhouse
409 New Lenox RoadTake a tour and learn about why some maple syrup is dark and some is light... Which is rarer... And the importance of weather!
Mountain Creek Farm, LLC
458 Schillings Crossing RdLebanon Valley Speedway
1746 US-20If you've got the need for speed!
High Lawn Farm
535 Summer Stcows, ice cream and charcuterie...oh my!
Clapp Park
233 W Housatonic Stgreat playground, splash pad and winter sledding!
Food Scene
Otto's Kitchen & Comfort
95 East StAmazing brunch! Get there before they run out of grits!
Bistro Zinc
56 Church StLa Fogata Restaurante
770 Tyler StFirefly Gastropub & Catering Co.
71 Church StSoooo good!
great views, great music, great wine! Bring the kids, too!
NOTE: it is not located where it is shown on the guidebook map. It is actually on the other side of Richmond Pond.
29 locals recommend
Balderdash Cellars
81 State Rdgreat views, great music, great wine! Bring the kids, too!
NOTE: it is not located where it is shown on the guidebook map. It is actually on the other side of Richmond Pond.
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan RdShopping
Lee Premium Outlets
17 Premium Outlet BoulevardGuido's Fresh Marketplace
760 S Main StUpscale, food shopping
Barrington Coffee Roasting Company
165 Quarry Hill RdOutdoors/Adventure
Great variety of hikes! See the beaver dams.
41 locals recommend
Mass Audubon's Pleasant Valley Wildlife Sanctuary
472 W Mountain RdGreat variety of hikes! See the beaver dams.
Zoar Outdoor Adventure Resort
7 Main StBe a daredevil!
Mount Greylock State Reservation Visitor Center
30 Rockwell RdHiking!
Ramblewild Adventure Park
110 Brodie Mountain RdBe a daredevil!
Ashuwillticook Rail Trail
Rail TrailGreat for biking
Ski Butternut
380 State RdJiminy Peak
Skiing!
Catamount Mountain Ski Resort
78 Catamount RdSkiing!
Bousquet Ski Area
101 Dan Fox DrSkiing!
Basin Pond
4-22 Becket RdThe Wahconah Falls Brook flows over several smaller falls before ending in the 40-foot Wahconah Falls. The cascade is scenic any time of year, but is especially impressive during the spring runoff.
Wahconah Falls
The Wahconah Falls Brook flows over several smaller falls before ending in the 40-foot Wahconah Falls. The cascade is scenic any time of year, but is especially impressive during the spring runoff.
The Ice Glen is a ravine in the southeast area of Stockbridge, Massachusetts. The park is essentially a lush, untended, romantic landscape consisting of piled rocks thick with mosses. Ice Glen derives its name from the fact that, ice can persist at the bottom of deep rock crevices there into the summer. Its north-south orientation protects the glen from much direct sunlight. Surrounding the glen is an old growth forest, rare in New England.
28 locals recommend
Ice Glen Trail
Ice Glen TrailThe Ice Glen is a ravine in the southeast area of Stockbridge, Massachusetts. The park is essentially a lush, untended, romantic landscape consisting of piled rocks thick with mosses. Ice Glen derives its name from the fact that, ice can persist at the bottom of deep rock crevices there into the summer. Its north-south orientation protects the glen from much direct sunlight. Surrounding the glen is an old growth forest, rare in New England.
Bash Bish Falls Trail in Mount Washington will take you to Massachusetts’ tallest single-drop waterfall. This hike is short and sweet with multiple access points so you can come back again and again. When you reach the waterfall, you can take a dip in the summer, view the foliage in the fall, and see the frozen falls in winter. No matter the time of year, Bash Bish Falls Trail is a great easy trail for everyone to hike to an incredible Massachusetts waterfall.
282 locals recommend
Bash Bish Falls State Park
Falls RoadBash Bish Falls Trail in Mount Washington will take you to Massachusetts’ tallest single-drop waterfall. This hike is short and sweet with multiple access points so you can come back again and again. When you reach the waterfall, you can take a dip in the summer, view the foliage in the fall, and see the frozen falls in winter. No matter the time of year, Bash Bish Falls Trail is a great easy trail for everyone to hike to an incredible Massachusetts waterfall.
Vine Gate Lavender Floral Farm
134 Whippoorwill RdCatamount Aerial Adventure Park
17 Nicholson RdCulture
The Mount, Edith Wharton's Home
2 Plunkett StNaumkeag
5 Prospect Hill RdNorman Rockwell Museum
9 Glendale RdCrane Museum of Papermaking and Center for the Paper Arts
32 Pioneer StBerkshire Botanical Garden
5 W Stockbridge RdShakespeare & Company
70 Kemble StJacob's Pillow
358 George Carter RdDance!
Mahaiwe Performing Arts Center
14 Castle StTanglewood
Frelinghuysen Morris House & Studio
92 Hawthorne StOzzie's Glass Gallery
1670 Pleasant StNecessities
Berkshire Medical Center
725 North StIn case of emergency
CVS
481 Pittsfield RdPharmacy
Price Chopper
Great for picking up milk, eggs, cider, etc.. and the BEST apple cider dunuts!
27 locals recommend
Bartlett's Orchard
575 Swamp RdGreat for picking up milk, eggs, cider, etc.. and the BEST apple cider dunuts!