Outdoor Activities

Horseback Riding

Berkshire Horseback Adventures – Guided trail rides along the beautiful shaded trails of Kennedy Park and Lenox Mountain. Horses available for all levels of riders ages 10+. Open daily from mid May through October. Lenox, MA

Undermountain Farm – Lovely farm that offers guided horseback trail riding as well as indoor and outdoor arenas and riding day camps. Lenox, MA.

Hot Air Balloon Rides

Worthington Ballooning – Experience the serenity of soaring high above the Berkshires. Take a scenic sunrise or sunset flight to create a fantastic lifelong memory. Worthington, MA.


Green Mountain Skydiving – Knock skydiving off your bucket list! With state-of-the-art training methods and experienced instructors, you will have a truly unforgettable experience. Bennington, VT. See the Innkeepers on their own skydiving adventure!

Hiking and Outdoor Water Adventures

Pleasant Valley Wildlife Sanctuary – Seven miles of trails that wind through hardwood forest, meadows, wetlands, and along the slopes of Lenox Mountain make this site an excellent location for hiking. Canoe trips are offered regularly on the Housatonic River and area lakes from mid-May through Columbus Day. Lenox, MA.

Monument Mountain – Known for its beautiful valley overview, historic landmarks, rock formations, small caves, long distance viewing. Moderate level hiking trails. Great Barrington, MA.

Appalachian Trail – 90 miles of hiking trails running through western Massachusetts with backcountry campsites and shelters.

Arcadian Shop – Equipping adventures for over 30 years. Gear, clothing, footwear & travel needs. 4-season rentals; bikes, kayaks, skis and snowshoes. Lenox, MA.

Berkshire Scenic Treks & Canoe Tours – Guided canoe tours. Enjoy the Housatonic’s abundant untouched beauty. Daily/evening. In winter months, enjoy guided snowshoe and hiking adventures. Pittsfield, MA.

Onota Boat Livery – Fish or play on Onota Lake. Boat rentals – canoes/kayaks/motor & pontoons. Marine sales, service and accessories. Slip rentals by day/week/season. Open daily year-round. Pittsfield, MA.

Ski Areas and Family Fun

Bousquet Mountain Ski Area – Year-round family fun. Downhill skiing/snow tubing/water slides/go-carts/mini-golf and pavilion and lodge. Pittsfield, MA.

Jiminy Peak Mountain Resort  – Premier 4-season resort and only resort powered by its own wind turbine. Skiing, riding and adventure park. Hanock, MA.

Ski Butternut – Downhill skiing and tubing. 22 trials, 10 lifts and ski shop. Affordable, family oriented and fun.  Great Barrington, MA.

Canterbury Farm Cross Country Skiing – Cross country ski on 22 km of groomed- tracked trails. Lessons available as well as ski, snowshoe and skate rentals. Becket, MA.

Cranwell Resort, Spa and Golf Club – 10 km of groomed cross country trails. Ski and snowshoe rentals. Group and private lessons. Lenox, MA.


Greenock Country Club – Donald Ross masterpiece of golf architecture from the classic age. Semi private club open to the public daily. 9/18 holes of golf available. Lee, MA.

Cranwell Resort, Spa and Golf Club – 18-hole championship par 70 course, GPS carts, driving range, Pro Shop, golf school. Golf Digest’s “Best Places to Play”. Lenox, MA.

Pontoosuc Lake Country Club – Scenic 18-hole par 70 public golf course on 100+ acres. Reasonable rates & twilight rates available. Snacks, beverages and rental clubs. Pittsfield, MA.

Stockbridge Golf Club – Stockbridge Golf Club members enjoy golf, tennis and a warm social experience in a friendly, informal, field club environment. The membership comes from a wide cross-section of the local population, as well as non-residents and second-home owners. Guests of The Gateways Inn can play at this private club if reservations are made through our Inn.  Greens fees are $90 per player Monday to Thursday, and $120 on Friday through Sunday and holidays.  Cart fees are additional. Club rentals are available. Stockbridge, MA.