Skiing and Winter Sports

Hilltop Orchards, home of JMash Cidery and Furnace Brook Winery

508 Canaan Road
Richmond, MA 01254

(413) 822-7334

Member Since: 2007

Enjoy the authentic working apple orchard vibe on our beautiful hilltop. Taste artisanal tree-to-can ciders, varietal wines. 20+ apple varieties, award-winning cider doughnuts, farm store, pick-your-own, hiking, snowshoeing. Open daily, 9-5.

Learn More | Visit Site | View on Google Maps

Berkshire East Mountain Resort

66 Thunder Mountain Road
Charlemont, MA 01339

Jon Schaefer

(413) 339-6617

Member Since: 2009

Berkshire’s premier adventure center! Zip lining, New England’s longest Mountain Coaster, whitewater rafting and Thunder Mountain Bike Park. Great skiing, snowboarding and tubing. 45 trails, terrain park, night skiing, children's programs, lessons and re

Learn More | Visit Site | View on Google Maps

Berkshire Bike and Board - Pittsfield

502C East Street
Pittsfield, MA 01201

Jay Elling

413-445-8888

Member Since: 2022

Full-service bicycle shop, one year free tune-ups on new bikes. Sales, service, group rides, fitting, apparel and all accessories. Bicycle rentals and ski leases.

Learn More | Visit Site | View on Google Maps

Notchview

Old Route 9
Windsor, MA 01270

Jim Caffrey

(413) 684-0148

Member Since: 2001

25 miles of scenic trails through forests high atop the Berkshires. Ski/snowshoe/hike. Two picnic shelters, cafe and equipment rentals.

Learn More | Visit Site | View on Google Maps

Berkshire Bike and Board

29 State Road
Great Barrington, MA 01230

Jay Elling

(413) 528-5555

Member Since: 2022

Full-service bicycle shop, one year free tune-ups on new bikes. Sales, service, group rides, fitting, apparel and all accessories. Bicycle rentals and ski leases.

Learn More | Visit Site | View on Google Maps

Bousquet Mountain

101 Dan Fox Drive
Pittsfield, MA 01201

Kevin McMillan

(413) 442-8985

Berkshires’ ski area since 1932, featuring 24 trails, night skiing/ riding in the winter, and weddings and concerts in the summer! All while boasting a year-round mountain-view restaurant.

Learn More | Visit Site | View on Google Maps

Onota Boat Livery

463 Pecks Road
Pittsfield, MA 01201

Caryn Wendling

(413) 442-1724

Member Since: 2002

Boat rentals: canoes/kayaks/motor/pontoons. Marine sales, service/accessories. Slip rentals by day/wk/season. During winter months, we serve as Berkshire County’s Ice Fishing Headquarters. Open daily year-round.

Learn More | Visit Site | View on Google Maps

Berkshire East Mountain Resort

66 Thunder Mountain Road
Charlemont, MA 01339

Jon Schaefer

(413) 339-6617

Member Since: 2009

Learn More | Visit Site | View on Google Maps

Ski Butternut

380 State Road
Great Barrington, MA 01230

Dillion Mahon

413-528-2000

Member Since: 2019

Skiing, riding, tubing. Family-friendly mountain with 22 trails and 100% snowmaking.

Learn More | Visit Site | View on Google Maps

Berkshires Outside

Laura Brennan

Member Since: 2024

Berkshires Outside is a user-friendly, comprehensive resource for all things outdoors, displaying over 550 assets from trailheads and tent sites to bike paths and beaches.

Learn More | Visit Site

Berkshire East Mountain Resort

66 Thunder Mountain Road
Charlemont, MA 01339

Jon Schaefer

(413) 339-6617

Member Since: 2009

Learn More | Visit Site | View on Google Maps

Jiminy Peak Mountain Resort

37 Corey Road
Hancock, MA 01237

Katie Fogel

(413) 738-5500

Largest ski/snowboard resort in southern NE. 45 trails/9 lifts/night skiing. Nationally recognized children's program/top rated lesson programs. Lodging, dining on site.

Learn More | Visit Site | View on Google Maps

Catamount Mountain Resort

Route 23
South Egremont, MA 01258

Rich Edwards

(413) 528-1262

Member Since: 1998

Four-season resort offering 44 trails for skiing/snowboarding plus snow tubing park. Ziplining and aerial adventure park and ropes course open in spring, summer, and fall.