Best Hikes Near Great Barrington, MA
It’s that time of year again—hiking season in the Berkshires. Nestled in the heart of the region, Great Barrington is a favorite for outdoor enthusiasts thanks to its diverse terrain, scenic vistas, and easy access to some of the area’s best trails. Whether you’re looking for a quick morning walk or a more challenging summit hike, there’s something here for every level.
Planning a spring escape? Here are five of our favorite hikes near Great Barrington, MA.
Monument Mountain
No list would be complete without Monument Mountain—one of the Berkshires’ most iconic hikes. Managed by The Trustees, this well-loved trail system offers multiple routes ranging from moderate to more challenging options.
The most popular loop (via Hickey and Peeskawso Peak) is closer to 3 miles round-trip, leading to dramatic cliff overlooks with sweeping views of the Housatonic River Valley. Along the way, you’ll pass through wooded trails, unique rock formations, and historic sites tied to Nathaniel Hawthorne and Herman Melville. It’s a must-do, just minutes from Little Lion Inn.
Flag Rock
For a shorter, quieter hike, Flag Rock is a local favorite tucked away just outside downtown. This roughly 1.5–2 mile out-and-back trail offers a moderate climb through the woods to a rocky overlook.
At the top, you’ll be rewarded with views of Great Barrington and the surrounding Taconic Range. It’s a quick but satisfying option—perfect if you want a scenic hike without committing to a full day.
Benedict Pond Loop
Located in Beartown State Forest, the Benedict Pond Loop is an easy, scenic 1.5-mile loop around a tranquil mountain pond. With relatively flat terrain, it’s ideal for all ages and skill levels.
This peaceful trail is especially popular for picnicking, wildlife spotting, and a leisurely walk along the water’s edge. Keep an eye out for turtles, birds, and other native wildlife—it’s one of the most relaxing hikes in the area.
Beartown State Forest Trails
Spanning over 12,000 acres, Beartown State Forest offers a wide network of trails for hikers looking to explore deeper into the Berkshires. In addition to the Benedict Pond Loop, you’ll find longer and more rugged routes throughout the forest.
For a more challenging outing, trails like the Appalachian Trail section through Beartown or connecting ridge hikes provide elevation, solitude, and rewarding views. It’s a great destination for those looking to go beyond the basics.
East Mountain State Forest
For a truly off-the-beaten-path experience, head to East Mountain State Forest, located just over the New York border near Great Barrington. This lesser-traveled area features rugged terrain, dense forest, and miles of quiet trails.
Hike to the summit for scenic views, or explore the network of trails that wind through the landscape. It’s ideal for experienced hikers or anyone looking to escape the more popular spots.
Stay at Little Lion Inn
As the Berkshires come alive in spring, there’s no better time to get outside and explore. From iconic peaks to hidden woodland trails, hiking near Great Barrington offers something for everyone.
Make Little Lion your home base—just minutes from Monument Mountain and a short drive to the region’s best outdoor adventures. Our cozy, pet-encouraging stay (with no pet fees) makes it easy to bring your four-legged hiking companion along for the journey.
Explore our offers to start planning your Berkshires getaway.