March 27th, 2024

The Best Hiking Near Great Barrington, MA

It’s that time of year again—hiking season! Located in the heart of the Berkshires, Great Barrington attracts outdoor enthusiasts of all kinds. With its diverse terrain and abundance of hiking trails, this charming town offers endless opportunities for exploration and discovery. Seeking a spring adventure? Here are our five favorite places to hike near Great Barrington, MA.

Stay at Briarcliff Motel

1. Monument Mountain

Monument Mountain

Of course, we have to start with this classic. Suitable for all skill levels and arguably one of the most iconic hiking destinations in the area, Monument Mountain offers breathtaking views and a rich history. Just a few minutes away from the Briarcliff Motel, this 1.5-mile loop trail leads to the summit, where hikers are rewarded with panoramic vistas of the Housatonic River Valley and the surrounding Berkshire Hills. Along the way, keep an eye out for unique rock formations and diverse wildlife—and remember it’s all about the journey.

2. Flag Rock

In search of a more secluded hiking experience? Flag Rock is tucked away in the woods off Division Street, a quite literal hidden gem featuring a moderate 1.6-mile out-and-back trail that leads to a stunning overlook. From the rocky outcrop known as Flag Rock, you can admire views of Great Barrington and the Taconic Range. This one is the epitome of short, yet rewarding. 

3. Benedict Pond Hike

Located within Beartown State Forest, the Benedict Pond Loop Trail is a photo-worthy hike around a mountain pond, a popular spot for fishing and picnicking. This 1.5-mile loop is perfect for hikers of all ages and skill levels, with relatively flat terrain and stunning scenery in every season. Stroll along the water’s edge, study the variety of trees in the surrounding forest, or search for beavers, turtles, and other wildlife—here, the choice is yours. 

4. Beartown State Forest Hikes

In addition to the Benedict Pond Loop Trail, Beartown State Forest is a 12,000 acre forest that offers a variety of hiking options for outdoor lovers. Miles of well-marked trails wind through the forests, along babbling brooks, and through scenic ridges. For a more challenging adventure, tackle the 6.5-mile Beartown Mountain Trail Loop. Once you see the stunning views that await you at the summit, you’ll be glad you did.

5. East Mountain State Forest

Venture to East Mountain State Forest, located just a short drive from Great Barrington and the Briarcliff Motel, for a truly off-the-beaten-path experience. This wilderness area features rugged terrain, extensive forests, and miles of secluded trails. Make a day out of it and hike to the summit of East Mountain for great views of the surrounding landscape, or wander along the relaxing streams. Honestly, we recommend doing both.

Stay at the Briarcliff Motel

As the snow melts and the forests again bloom into spring, take advantage of the beauty that surrounds you and opt to explore the stunning Berkshires. Hiking near Great Barrington, MA is what you should be doing this weekend. So book your stay at our charming and pet-friendly motel in the Berkshires: the Briarcliff Motel