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  • Lowest Rate Guaranteed
  • Complimentary WiFi
  • Full Gourmet Country Breakfast
  • Whirlpool (some rooms)
  • Fireplaces (some rooms)
  • Outdoor heated pool (seasonally)
  • 36 acres of land with 2 hiking trails and an outdoor fire pit
  • Complimentary night cap station

Top Outdoor Activities in the Berkshires

So much to do and so little time. That about sums it up when thinking about the top outdoor activities in the Berkshires. Hiking, biking, and kayaking may be tops for some. However, ziplining, white water rafting, and hot air ballooning rank high for adrenaline junkies. And the beauty of it all? Everything is right here in western Massachusetts, just minutes from our elegant country retreat in Lee, MA.

We can point you in the right direction for any outdoor adventure that appeals. But first, take a look at our outdoor experience packages. If you’re looking for something different to do in the great outdoors, we can help! We’ve put together a few of our favorite ways to make your next visit to the Berkshires extra special. Saddle up and join a knowledgeable guide for a leisurely trail ride on horseback. Slip into the cockpit of a sleek kayak and meander down river watching local wildlife in their natural habitat. Or connect with the great outdoors on a meditative hike with an experienced naturalist. Most adventures last approximately 2 hours and include everything from instruction to equipment.

However, if you want to freelance your outdoor activities, we have a long list of recreational pursuits for you to consider. 

Hiking Trails

Hiking in the woods clears your mind and restores your spirit and is often one of our favorite outdoor activities. With so many great hikes to choose from here in western Massachusetts, it helps to have a little upfront info on distance, elevation, and terrain. We recommend starting with one of these 5 amazing hikes. Each one offers awesome scenic beauty. Whether you’re on a short out-and-back trail or a more challenging multi-mile loop course, the views will be lovely.

Waterfall Treks

Surprisingly, 8 epic waterfall hikes are within a 30- to 40-minute drive of the Devonfield Inn in Lee, MA. With a little effort and some sturdy hiking boots, each trek rewards in spades in terms of natural beauty and awe-inspiring scenery. Of course, the big daddy of all hikes in western Massachusetts is Bash Bish Falls. It is considered the crowning jewel of waterfall hikes in the Berkshires. Bash Bish Falls drop 80 vertical feet down a rockface into a deep emerald pool.

Biking Trails

According to John F. Kennedy, “nothing compares to the simple pleasure of a bike ride.” And we couldn’t agree more. Set off on the main streets and back roads of the Berkshires for an afternoon amble along winding routes through neighboring towns and villages. Or head up to the Ashuwillticook Rail Trail, a 12.7-mile paved trail that hugs the shoreline of the Hoosic River. Traveling through the towns of Cheshire, Adams, and Lanesborough, you’ll be privy to outstanding views of nature and wildlife. 

Kayaking and Canoeing 

This region of outstanding beauty may be best seen from the cockpit of a canoe or kayak. As Ratty said to Mole in The Wind in the Willows, “Believe me, my young friend, there is nothing – absolutely nothing – half so much worth doing as simply messing about in boats.” Join Berkshire Canoe and Kayak Tours, a family-owned outfitter, for a flatwater paddle along the Housatonic River. Keep an eagle eye out for the abundant wildlife that frequent the shoreline.

Hot Air Ballooning

Soaring above the rolling hills of the Berkshires in a hot air balloon is one of those experiences that literally changes your life. Sailing silently as air in a basket guided expertly by your balloon pilot over hills and dales at sunrise or sunset is, in a word — magical. Catch the ride with Worthington Ballooning like we did. They’ve been offering balloon rides over the Berkshires for over 15 years. Or you can try Spirit Ballooning out of  Canaan, CT, but offering launches from various locations in the Berkshires.

Horseback Riding

Giddy up and hit the trails with Berkshire Horseworks for an equine adventure wandering through the woods on a sturdy steed. They provide individual, couples, or small group rides include instruction and 1-2 hours of riding through the bucolic landscape of western Massachusetts.


Sail through the treetops on an aerial adventure with Zoar Outdoor. With 11 ziplines, 2 sky bridges, and 3 rappels, once you learn the basics of braking and proper positioning, you’ll fly free as a bird through the green canopy high above the Deerfield River Valley. The 3 hours you spend soaring through the trees will no doubt be the cause of your big, beautiful smile at the end of the day.

White-Water Rafting

Choose from a variety of white-water rafting tours with Zoar Outdoor Rafting. From a gentle half-day family float to a challenging Class IV rapids adventure, your expert guides will lead the way to an exciting day on the water.

So, the next time you’re looking to up the ante on your bed and breakfast getaway to western Massachusetts, consider tackling one of our top outdoor activities in the Berkshires. There’s something about being outside in the fresh air that we find infinitely refreshing. Relax, refresh, renew, it’s all about you in 2022.

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