Great Outdoors


Monument Mountain

From the 1,642-foot summit of this popular peak—which once drew 19th-century literary giants—gaze across the splendor of the Housatonic River Valley.

Mount Greylock

The granddaddy of Berkshires hiking - Mount Greylock. Located in North County, the Berkshires’ primo natural landmark looms high above the surrounding Berkshire landscape reaching 3,491 feet. (Pet Friendly)

The Appalachian Trail

The AT’s 2,000-mile trail cuts directly through the Berkshires over the top of Mt. Greylock and there are numerous entrances to the trail through the area, many connected off of local paths. (Pet Friendly)

Bear Mountain

One of the longest hikes in the Berkshires, the 10.5-mile Bear Mountain trail is an ambitious, all-day hike winding from Salisbury, CT to Sheffield, MA. Spectacular vistas of Bear and Race Mountains. (Pet Friendly)

October Mountain

Bordering Washington, Becket, Lee and Lenox, October Mountain’s 16,500 acres is the largest state forest in Massachusetts offering trails for hiking, mountain biking and XC skiing and snowshoeing. (Pet Friendly)

Laura’s Tower & Ice Glen

This quiet, wooded 1.5-mile trail ascent winds through pines and hemlocks by Ice Glen (a glacial ravine) and ends at a summit tower with panoramic view of mountains in three surrounding states.

Pleasant Valley Wildlife Sanctuary

Set amidst more than 1,000 lush acres, Pleasant Valley’s varied trails wind through forests, meadows, and wetlands along the slopes of Lenox Mountain.

Kennedy Park

A pleasant surprise just minutes from historic Lenox, Kennedy Park is hardwood forest whose groomed trails snake their way through 502 acres of tree-lined forest.

Hilltop Orchards

Best known for apples and the Furnace Brook Winery, Hilltop offers miles of groomed moderate and challenging terrain with separate trails specifically designed for snowshoeing. (Pet Friendly)

Pittsfield State Forest

A sprawling 1000-acre forest located in the town of Pittsfield, this year-round destination offers 30 miles of trails – many specifically marked for winter activity. It’s a pretty rustic set-up.


Ashuwillticock Rail Trail

This 11.2-mile former rail trail is an easy circuit for those looking for a less challenging bike path. This mostly flat surface runs from the Berkshire Mall in Pittsfield to Adams. (Pet Friendly)

Housatonic Bike Routes

Another great ride is the 45-five mile stretch that traverses the Housatonic River Valley. There are some tough climbs, flat stretches, dirt roads, scenic views, smooth pavement, farms, waterfalls.

Mount Everett Climb

A combination of beautiful Berkshire and New York landscapes, this 40-mile ride is one of the most challenging rides in the Berkshires.

Mount Greylock

Mount Greylock provides the ultimate cycling experience in Massachusetts, offering several scenic vistas on the ascent, plus a thrilling roller coaster of a descent. (Pet Friendly)

Berkshire East Mountain Resort

At Berkshire East’s Thunder Mountain Bike Park, beginners and double-black trail riders alike can experience the New England's fastest growing mountain bike park.

On the Water

Crab Apple Whitewater

Enjoy an outstanding white-water rafting adventure on the Deerfield River. But even if you’re taste for adventure runs a little milder, this outdoor outfitter has a trip that is just right for you.

Zoar Outdoor

A leader in outdoor adventure offering white water rafting in Massachusetts and Vermont, zip line canopy tours in the Berkshires, plus kayaking and canoeing trips.

Canoe Meadows

View scenic woods, fields, and wetlands in this wildlife sanctuary which attracts warblers, turtles, ospreys and otters, at different times of year.

Berkshire Canoe Tours

“Quietwater” paddling means scenic canoeing or kayaking on lakes, ponds, and relatively calm rivers. Western Massachusetts has some splendid rivers and lakes for “quietwater”.


Catamount Adventure Park

An exciting aerial forest adventure that provides a variety of courses that are fun for all ability levels. With 12 treetop courses of varying difficulties, you'll cross bridges and climb obstacles.


A tree-to-tree adventure destination, eight aerial obstacle courses meander through the trees at various heights and include 15-17 elements including high wires, zip lines, and rope ladders.

Jiminy Peak

The area’s most popular ski resort also offers an off season aerial adventure park, mountain biking and an adventure park with mountain coaster, zip line, alpine slide and scenic chairlift rides.


Stockbridge Golf Club

Founded in 1895, this exclusive golf and tennis club is nestled in a tranquil mountain setting on the banks of the Housatonic River.

Donnybrook Country Club

Located in Lanesborough, this is one of the Berkshire’s most unique public golf courses with spectacular views on a championship layout.

Bas Ridge Golf Club

An 18-hole course with character, incredible greens and spectacular views! Open to the public. Affordable golf at its best.

Wahconah County Club

Picturesque 18-hole, premier course in the central Berkshires. Excellent conditions. Challenging play. Titleist rentals. Lessons. Range. Pub.

Egremont Country Club

Combine the prestige of a country club setting with affordable pricing. Beautifully nestled among the Berkshire mountains with a panoramic views of the golf course.

Ski and Snowshoe


With tubing on weekends and holidays, a terrain park, 1,000-foot vertical and 22 trails, this ski area, located in Great Barrington, appeals to little ones, novices and experts alike.

Bousquet Ski Area

Located on the outskirts of Pittsfield, this ski area also has tubing and a casual, familiar atmosphere with stunning views of Mount Greylock, the highest point in Massachusetts.

Jiminy Peak

Jiminy Peak is tops for ski and snowboard enthusiasts in southern New England. With 45 trails and nine lifts, this Hancock, MA ski slope also offers night skiing, lessons and snowshoeing.

Catamount Ski Area

Just across the state line in Hillsdale, NY, Catamount features the steepest run in the Berkshires. First opened in 1939, Catamount is one of the oldest original operating ski areas in the Northeast.


With 3,000 acres of rolling terrain and 25 miles of trails, this is an idyllic escape for cross-country skiers and snowshoeing alike. Seventeen kilometers of groomed and track-set trails.

Kennedy Park

Situated in the historic village of Lenox. The Park’s 502 acres of tree lined forest features 15 miles of trails carved out of a network of old carriage roads. A variety of terrains for all levels. (Pet Friendly)