Outdoor Recreation


Our winters may be long, but so is the list of ways to get out there and have some winter fun. From alpine to Nordic skiing, snowshoeing to ice skating, there are lots of way to avoid being cooped up inside until Spring.

Downhill Skiing

Butternut – With tubing on weekends and holidays, a terrain park and 110 skiable acres, this ski area, located in Great Barrington, appeals to little ones, novices and experts alike. It’s a mid-size mountain with 1,000-foot vertical and 22 trails.”

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. A village center contains restaurants and shops.

Bousquet Ski Area – Located on the outskirts of Pittsfield, the largest city in the Berkshires, this area is known for its casual, familiar atmosphere and stunning views of Mount Greylock, the highest point in Massachusetts. ” This destination offers tubing, night skiing and two terrain parks.

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. Find a variety of carpets and lifts, night skiing, a terrain park and lessons.

Cross Country Skiing & Snowshoeing

Notchview – 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 trails are groomed and trackset for classic cross-country skiing. You can also go off track and explore the backcountry, or snowshoe alongside the ski trails.

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.

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. While there are a variety of terrains, including several moderate climbs, the park’s trails are predominately flat and smooth. However, the trails are not groomed.

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. No bells and whistles here. Just lots of majestic outdoor scenery and hearty trail excursions.

Mt. Greylock – The ultimate challenge for snowshoeing in Western Massachusetts. Reaching a peak of 3,491 feet, it is the highest point in Southern New England. What’s more, there are few mountains in the Northeast with as much diversity and access. There are over 70 miles of trails, many of which can be trekked in winter.


With literally hundreds of walking paths, foot trails and steep climbs to majestic overlooks, many folks prefer to explore our spectacular surroundings on foot So grab a backpack, lace up your boots and get an up close and personal look at the Berkshires

Mount Greylock – The granddaddy of Berkshires hiking. Follow in the footsteps of Thoreau to the highest peak in southern New England and be rewarded with a sweeping vista that encompasses five states.

Monument Mountain – Another of the more recognized landmarks in the Berkshires. A true hotspot for hiking in the Berkshires, this mountain features three miles of trails that wind through a white pine and oak forest to a summit with a spectacular overlook of the Berkshires below.

Kennedy Park – A pleasant surprise just minutes from historic, downtown Lenox. Kennedy Park is a town-owned and maintained hardwood forest whose groomed trails snake their way through 502 acres of tree lined forest. Excellent for casual strolling, hiking, mountain biking, horseback riding, even cross country skiing and snowshoeing in the winter.

Bear Mountain – One of the longest hikes in the Berkshires, the 10.5-mile Bear Mountain trail. This ambitious, all-day hike winds from Salisbury, CT to Sheffield, MA. Along the way you’ll discover some stunning, panoramic views of South County that are as good as it gets. – especially the spectacular vistas from the summits of Bear Mountain and Race Mountain.

October Mountain – Bordering the towns of Washington, Becket, Lee and Lenox, October Mountain’s 16,500 acres make it the largest state forest in Massachusetts. Forest trails are available for hiking, mountain biking, cross-country skiing, and off-road vehicle use.

Laura’s Tower & Ice Glen – Within walking distance of the Inn, this quiet wooded 1.5 mile trail ascent winds through pines and hemlocks, by the Ice Glen (a glacial ravine) and ends at a summit with a tower that offers a panoramic view that encompasses the middle Berkshires, Mt. Greylock, the New York Catskills to the west and the Green Mountains of Vermont to the north.

Pleasant Valley Wildlife Sanctuary – Set amidst more than 1,000 lush acres in the Berkshires, Pleasant Valley’s varied trails wind through forests, meadows, wetlands, and along the slopes of Lenox Mountain, making this site an excellent location for easy-to-strenuous hiking.

The Appalachian Trail – The AT’s 2,000 mile trail cuts directly through the Berkshires. There are numerous entrances to the trail through the area, many connected off of local paths. The trail snakes through some incredibly scenic spots, including Race Brooks Falls, the imposing and impressive hardwood forests in the western part of the state, and, of course, Mt. Greylock.

The Berkshire Hiker—I will create a fabulous hiking experience for you on our beautiful Berkshire trails. My knowledge and skills ensure a safe and enjoyable outdoor adventure. Whether you are a beginner or expert, I will personally design a Berkshire hiking experience for your interests, your abilities and your time schedule. I’ve been leading successful hikes in the Berkshires since 2007.


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 up north to Adams.

South County Routes – The best places to traverse the county on two wheels and experience the area’s historical, cultural and natural resources can be found in a number of South County routes through the five communities of Lenox, Lee, Great Barrington, Stockbridge and Sheffield,

Housatonic Bike Routes – Another great ride is the forty-five mile stretch that traverses the Housatonic River Valley. There are some tough climbs, flat stretches, dirt roads, scenic views, smooth pavement, farms, waterfalls and small villages along the ride.

Mount Everett Climb – A combination of beautiful Berkshire and New York landscapes, this is one of the most challenging rides in the Berkshires. This 40 mile ride, starting in South Egremont, MA, climbs past Mount Everett, the second highest mountain in the state, by Bash Bish Falls and ends in the tiny hamlet of Copake Falls.

Berkshire East Mountain Resort – At Berkshire East’s Thunder Mountain Bike Park, mountain biking is the name of the game. From beginners to double-black trail riders, bikers can experience the thrills of racing down intricately crafted courses at New England’s fastest growing downhill mountain bike park.

Mount Greylock – At the top of many of our lists of outdoor pursuits, Mount Greylock provides the ultimate cycling experience in Massachusetts, offering several scenic vistas on the ascent, plus a thrilling roller coaster of a decsent. An easier loop is also available.


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.

Canoe Meadows– Here’s an opportunity to take a naturalist-guided canoe trip along the Housatonic River from April to October.

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” canoeing. Berkshire Canoe will take you there, and even help provide you with a boat and gear.

Local Lakes – There are also a number of other nearby lakes for canoeing and kayaking. They include Stockbridge Bowl, Goose Pond and Lake Buel.


Zoar Outdoor – New England’s leader in outdoor adventure offering white water rafting in Massachusetts and Vermont, zip line canopy tours in the Berkshires, plus kayaking and canoeing trips and kayak instruction.

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 are challenged to cross bridges, climb ladders, obstacles and zip lines.

Ramblewild – 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, rope ladders, log cargo nets and suspended bridges.

Jiminy Peak – The area’s most popular ski resort also offers an off season aerial adventure park, a mountain adventure park and mountain biking.

Bousquet – Another multi-purpose ski resort, offers an adventure park, camps, a ropes course, zip lines, waterslides, disk golf, go karts, mini golf, bounce house, obstacle course, climbing wall & more.


For many travelers, no real getaway is complete without a couple rounds of golf. We have plenty of courses where you can do just that in the Berkshires.

Wyndhurst Manor & Club – Named one of “The Best Places to Play” by Golf Digest, this historic 18-hole course combines spectacular views and challenging golf.

Stockbridge Golf Club – Founded in 1895, this golf and tennis club is nestled in a tranquil mountain setting on the banks of the Housatonic River just down the street from the Red Lion Inn Village.  This is a members-only club, however, special arrangements can be made for guests of The Village by calling our Reservations Department in advance.   Tee times are based on availability.

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.