One of the most frequent requests of our guests is where to go for the best easy-to-moderate hikes in the Berkshires. Fortunately, we don’t lack great trails to recommend. Depending on your ability, you’ll find gentle walks along lakes and ponds or more moderate treks deep in the woods to thundering waterfalls. You can even tackle an 8.4-mile portion of the Appalachian Trail from the trailhead in Lee, MA.
But right here on the grounds of our charming bed and breakfast in the Berkshires, we realized that with 32 sprawling acres, blazing a walking trail for our guests to enjoy year-round would add tremendous value to their stay. Hence Doug’s brainchild created two lovely walking trails right here on our property. Take the Meadow Trail to wander among wildflowers all along the tree line for a tranquil, easy stroll. Or, for those looking for something a bit more of a backwoods experience, try the Wilderness Trail that meanders through the woods for about a mile. And, right in the heart of it all, you’ll find a peaceful picnic spot to relax and commune with nature.
However, the hills and mountains surrounding us offer abundant hiking opportunities. Be sure to pack a sturdy pair of boots, perhaps some bug spray, and head out for an exhilarating walk through the countryside. Here are some of our favorites. Just copy the coordinates into Google Maps, and you’re off!
Tyringham Cobble Loop, Tyringham, MA
GPS Location: 42.240332372 -73.205499178
Cobble Loop is a 2.1-mile hike that features beautiful wildflowers and a great spot for bird-watching. Dogs are welcome (on leashes), and a portion of the trail merges with the famous Appalachian Trail. This is one of Doug’s favorites to hike.
Housatonic Flats, Great Barrington, MA
GPS Location: 42.216357, -73.343895
Located close to the center of Great Barrington, the Housatonic Flats trail offers an easy 1-mile loop along the Housatonic River. Perfect for a laidback 30-minute walk watching the river run and keeping an eye out for abundant wildlife.
Parsons Marsh Reserve and Trail, Lenox, MA
GPS Location: 42.3644, -73.3049
Traversing an open meadow to a small pond, Parsons Marsh is the ideal accessible short hike for everyone. Featuring hard-packed gravel and a boardwalk through forested wetlands, the serene setting features ample opportunity to observe the flora and fauna that thrive in the environment here.
Basin Pond, Lee, MA
GPS Location: 42.2959, -73.1612
For a moderately challenging 2.5-mile hike, you can’t beat Basin Pond right here in Lee, MA. The trail takes you across streams, through a natural amphitheater strewn with boulders, to a viewing platform at the water’s edge. From the platform, you may spot moose and beavers.
Stevens Glen, West Stockbridge, MA
GPS Location: 42.3505, -73.3484
For a moderately difficult hike to view a spectacular waterfall, Stevens Glen never disappoints. This clearly marked 1.5-mile trail meanders through forests of white pine and hemlock to a rock cleft. Here the Lenox Mountain Brook cascades down a deep ravine to the stream below. On a hot summer’s day, you’ll see many folks wading in the cool water.
Olivia’s Overlook at Yokun Ridge South, Lenox, MA
GPS Locations:
42.3519, -73.3377 (Olivia’s Overlook- Charcoal and Burbank trailhead parking)
42.3543, -73.3292 (Brothers Trail and Old Baldhead Road trailhead parking)
You’ll have several options to hike when you visit Yokun Ridge South, a reserve located in the heart of the Berkshires that encompasses Lenox, Richmond, Stockbridge, and West Stockbridge. Olivia’s Overlook is the main draw for its spectacular view of Monument Mountain. From the overlook, four separate trails lead through mountain laurel, hemlock, pine, and poplar. Be on the lookout for barred owls who particularly like this habitat.
- Charcoal Trail: 1.6 miles roundtrip
- Brothers Trail: 0.9 miles one-way
- Burbank Trail: 3.2 miles round-trip
- Old Baldhead Road: 1.5 miles, one-way
Before you head out on one of our recommended best easy-to-moderate hikes in the Berkshires, be sure to check the trail conditions. Pack some water and perhaps one of our gourmet picnic baskets. And if you’re in the mood to stay closer to home, you can always meander through the gardens and trails on our 32-acre property. Happy trails to you!
