What to do in the Berkshires – Get out and see it!

Looking at what to do in the Berkshires? There are so many fun things to do: take a hike to see breathtaking waterfalls, explore the region’s historic sites, have a picnic lunch in one of Massachusetts’ state parks or hit the slopes for a day of skiing. No matter the season, the Berkshires offer plenty of opportunities for things to do including lots of outdoor adventures.

Berkshires Hiking & Biking

Bash Bish Falls State Park

Next to the Mount Washington State Forest, Bash Bish Falls is about 60 feet and is one of Massachusetts’ highest single-drop waterfalls. An easy hike with incredible views.

Monument Mountain

Photo Courtesy Mwanner, licensed under Attribution-ShareAlike 4.0 International

Located in Great Barrington, Monument Mountain, a 2.8-mile hike, is incredibly popular among Berkshire adventurers. Get rewarded with views of Beartown State Forest and Taconic Range once you reach the top.

Mount Greylock

The beauty of this mountain can be taken in while hiking or from the comfort of your vehicle. Hike or drive to the top for amazing views of the region.

Appalachian Trail

Ask us for directions to Tyringham Cobble, which crosses over the Appalachian Trail. A challenging two-mile hike to the top with picnic areas along the trail

Ashuwillticook Rail Trail

This 11-mile rail-trail offers the opportunity for walking, biking, skating, and cross-country skiing. The trail passes through the Hoosic River Valley.

Pleasant Valley Wildlife Sanctuary

Located in nearby Lenox, MA, this wildlife sanctuary is an easy, family-friendly hike. Explore more than seven miles of forests, meadows, and wetlands. Visitors can also take advantage of guided tours, bird walks, and canoe trips. Admission is $5 for adults and $3 for children and seniors.

The Stockbridge Bowl

The Stockbridge Bowl, also known as Lake Mahkeenac, is a 372-acre lake 2.5 miles north of Stockbridge, Massachusetts. Stockbridge Bowl is the largest lake within the Town of Stockbridge, with a public boat ramp making the lake accessible to all. Throughout the year, the lake is extensively used by canoers, kayakers, sailers, swimmers, waterskiers, powerboaters, and fishermen.

Golfing in the Berkshires

Stockbridge Golf Club
Ask us to make you a reservation at the beautiful Stockbridge Golf Club and save! Rates: Monday through Thursday – $90.00 with our referral (cart not included); Friday through Sunday and Holidays – $120.00 with our referral (cart not included)

Wyndhurst is an 18-hole historic par 69 course, 10-acre driving range, with scenic views of the Berkshires. One-on-one golf instruction is also available for beginners.  Call (877) 781-7125 for more information.

Greenock Country Club
This scenic 9-hole golf course in Lee, Massachusetts is open to the public seven days a week. Call (413) 243-3323 for more information.

Berkshires Skiing, Snowboarding, & Tubing

Ski Butternut

About 15 minutes from the Inn at Stockbridge, Ski Butternut offers snow tubing, downhill skiing, and lessons for all ability levels.

Bousquet Mountain

Enjoy downhill skiing, snowboarding, and snow tubing at Bousquet in Pittsfield, MA.

Hot Air Ballooning in Massachusetts

Spirit Ballooning
Based out of Canaan, CT, Spirit Ballooning launches their hot air balloons from various locations in the Berkshires. Take off any time of the year for unparalleled views of the Berkshire Mountains region.

Misty River Ballooning
Take an unforgettable ride of your life and float high above the Pioneer Valley of Massachusetts with Misty River Ballooning and see far and wide the beauty of New England.

Ziplining & Adventure Parks

Bousquet is a great place for skiing in the winter, but it turns into an awesome place for adventure when summer comes around. Between the adventure park, ropes courses, zip lines, waterslides, and much more, you’ll be sure to find something to do here.

Zoar Outdoor
Just over an hour from our bed & breakfast, Zoar Outdoor is the ultimate outdoor recreation facility. Go whitewater rafting, zipping through the trees all day long, or enjoy the water on a stand-up paddleboard or kayak.

Berkshire East
While enjoying the fun at Zoar Outdoor, consider also stopping over to the Berkshire East Mountain Resort and take a thrilling ride on their Thunderbolt Coaster, a mountain coaster unlike any other!