Outdoor Activities in The Berkshires

Top Outdoor Activities in The Berkshires

The Berkshires is a beautiful region located in western Massachusetts that is renowned known for its scenic trails, pristine forests, and breathtaking mountain views. Here are a few favorite outdoor activities and how far they are from Stockbridge Country Inn – your cozy home base for adventure.

Hiking in the Berkshires
Hiking is one of the most popular outdoor activities in the region, thanks to its well-marked trails and inspiring scenery. One must-see destination is Mount Greylock, the highest peak in Massachusetts, offering panoramic views of the surrounding valleys. The summit is approximately 25 miles from our Inn.

Another beloved spot, Monument Mountain, features moderate trails with spectacular views of the from the Housatonic River Valley – just 5 miles from our Stockbridge bed and breakfast.

Biking
Prefer two wheels to two feet? The Berkshires rolling hills and peaceful country roads make it a cyclist’s dream. The region is home to a number of scenic bike routes, ranging from easy, family-friendly rides to challenging mountain biking trails. One popular route is the Ashuwillticook Rail Trail – an 11 mile path through picturesque towns and lakes – is ideal for riders of all abilities. The trailhead is roughly 20 miles from our Inn.

For a more challenging ride, head toward Pittsfield State Forest, which spans more than 11,000 acres, and offers trails ranging from easy to advanced. After a day of exploring, return to your Berkshires guest room and unwind with a glass of wine or cozy up by the fireplace. The distance to Pittsfield State Forest is approximately 10 miles.

Fishing
The Berkshires is home to some of the best fishing in the Northeast, with numerous lakes, streams, and rivers offering opportunities to catch a variety of fish species. One popular spot is the Housatonic River, which is known for its trout and smallmouth bass populations. Other popular fishing destinations include Laurel Lake, Pontoosuc Lake, and Onota Lake. The distance from The Stockbridge Country Inn to the Housatonic River is approximately 2 miles.

Kayaking and Canoeing
Kayaking and canoeing are great ways to explore The Berkshires’ many waterways. There are a variety of outfitters in the region that offer rentals and guided tours, making it easy to get out on the water. The Housatonic River is a popular spot for kayaking and canoeing, as are Stockbridge Bowl and Lake Mahkeenac. The distance from The Stockbridge Country Inn to Stockbridge Bowl is approximately 2 miles.

Golfing
The Berkshires is home to a number of excellent golf courses, with options for golfers of all skill levels. One popular course is the Cranwell Spa & Golf Resort, which offers stunning views of the surrounding mountains. The course is known for its challenging layout, with water hazards and bunkers throughout. Other popular courses include Wyantenuck Country Club and Stockbridge Golf Club. The distance from The Stockbridge Country Inn to the Cranwell Spa & Golf Resort is approximately 3 miles.

Horseback Riding
For a unique outdoor experience, consider taking a horseback ride through The Berkshires’ scenic countryside. There are a number of stables and riding schools in the region that offer guided rides for riders of all levels. One popular destination is Undermountain Farm, which offers scenic trail rides through the forest and countryside. The distance from The Stockbridge Country Inn to Undermountain Farm is approximately 20 miles.

Skiing and Snowboarding
During the winter months, The Berkshires become a playground for skiers and snowboarders. The region is home to several ski resorts, including Jiminy Peak and Bousquet Mountain. Jiminy Peak offers a variety of trails for skiers and snowboarders of all levels, as well as a terrain park for freestyle enthusiasts. Bousquet Mountain is a smaller, family-friendly resort that offers affordable lift tickets and lessons. The distance from The Stockbridge Country Inn to Jiminy Peak is approximately 25 miles.

Rock Climbing
If you’re looking for a challenge, consider trying your hand at rock climbing in The Berkshires. The region offers several excellent climbing destinations, including Rose Ledge, a popular spot for both beginner and experienced climbers. Other popular climbing destinations include Farley Ledge and Chapel Ledges. The distance from The Stockbridge Country Inn to Rose Ledge is approximately 15 miles.

Ziplining
For a thrill-seeking adventure, try ziplining through the forests of The Berkshires. One popular ziplining destination is Berkshire East Mountain Resort, which offers several zipline tours that soar through the treetops. The tours range in length and difficulty, making it a great activity for families and adventurers alike. The distance from The Stockbridge Country Inn to Berkshire East Mountain Resort is approximately 50 miles.

Birdwatching
The Berkshires is a popular destination for birdwatchers, thanks to its diverse range of bird species and habitats. Some popular birdwatching spots include Mount Greylock State Reservation, which is home to a variety of bird species, including the rare Bicknell’s Thrush. Other popular birdwatching destinations include Pleasant Valley Wildlife Sanctuary and the Canoe Meadows Wildlife Sanctuary. The distance from The Stockbridge Country Inn to Mount Greylock State Reservation is approximately 25 miles.

Outdoor Adventures Year-Round

The Berkshires offer outdoor fun in every season – kayaking and swimming in summer, skiing and snowshoeing in winter, and scenic drives or leaf-peeping in fall. No matter when you visit, you’ll find activities that complement every type of traveler.

Plan the perfect mix of adventure and relaxation with our Berkshires getaway specials or browse our rooms and suites in Stockbridge for your next outdoor retreat.