Great Barrington, a region in the Berkshire Mountains of Western Massachusetts, is characterized by its diverse landscapes, extensive forested areas, and scenic river valleys. Approximately 69% of the town is forested, with another 10% dedicated to farmland and pasture, providing a natural backdrop for outdoor activities. The terrain includes forested mountains, river valleys, and state forests, offering varied options for several sports like hiking, road cycling, jogging, and touring cycling. The Housatonic River flows through the area, providing accessible points…
47
Routes
4.8
(17)
Average rating
382
People visited

4.8
(5)
92
hikers
3.92km
01:17
170m
170m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

5.0
(1)
14
hikers
3.02km
00:47
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

2
hikers
15.9km
04:25
290m
300m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

1
hikers
7.41km
02:18
260m
270m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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41
riders
60.9km
02:44
630m
630m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

15
riders
50.2km
02:13
470m
470m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

15
riders
41.0km
01:52
380m
380m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

10
riders
51.2km
02:33
490m
490m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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4
runners
11.7km
01:16
170m
170m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3
runners
8.56km
01:02
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3
runners
4.87km
00:32
110m
100m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

3
runners
6.01km
00:43
70m
70m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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2
riders
46.9km
03:06
430m
430m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.0
(1)
2
riders
37.1km
02:11
210m
210m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

2
riders
40.7km
02:35
220m
220m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

2
riders
22.9km
01:27
190m
190m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Great Barrington offers a variety of outdoor activities including hiking, road cycling, jogging, and touring cycling. The region features diverse landscapes with forested mountains, river valleys, and state forests. There are more than 40 routes available for exploration.
Popular hiking areas include Monument Mountain Reservation, offering trails like the Peeskawso Peak loop with scenic vistas. Beartown State Forest also provides options such as the Benedict Pond via Appalachian Trail and Mount Wilcox Trail Loop. For more options, refer to the Hiking around Great Barrington guide.
Yes, Great Barrington offers several easy options. The Great Barrington River Walk follows the Housatonic River and is a gentle path close to town. The Housatonic Rail Trail is a 0.75-mile (1.2 km) crushed-stone path suitable for walking. The Peeskawso Peak loop at Monument Mountain is also considered an easy 2.4-mile (3.9 km) trail. For more, see Easy hikes around Great Barrington.
Great Barrington provides numerous road cycling opportunities through picturesque valleys and along the Housatonic River. Routes often feature scenic views of the Berkshire Mountains and rural landscapes. Cyclists can find detailed options in the Road Cycling Routes around Great Barrington guide.
Joggers can explore various trails and paths throughout the region's natural beauty. The Housatonic Rail Trail is a good option for a shaded, family-friendly experience. Mcallister Park also offers over 88 acres of trails suitable for running. More routes are available in the Running Trails around Great Barrington guide.
The region features the Housatonic River, which flows through the town, and Monument Mountain Reservation, known for its scenic vistas. Beartown State Forest includes Benedict Pond, a popular spot for recreation. East Mountain Forest offers a quiet pond and scenic views overlooking Great Barrington.
Yes, komoot offers several guides for Great Barrington. These include Hiking around Great Barrington, Easy hikes around Great Barrington, and Road Cycling Routes around Great Barrington. Guides are also available for jogging and touring cycling.
Great Barrington is a popular destination on komoot, with more than 800 visitors sharing their experiences. The routes in the region have an average rating of 4.91 out of 5 stars. There are 40 routes available across various sports.
Yes, almost 4 miles (6.4 km) of the renowned Appalachian Trail pass through the Great Barrington community. This provides opportunities for hikers seeking longer excursions and experiencing a segment of the iconic trail.
The Thomas & Palmer Brook Reserve is a 333-acre reserve in Great Barrington. It features 2 miles (3.2 km) of trails, including an accessible Meadow Loop and more moderate Woodland and Whale Rock Trails. The reserve offers views across wetlands and large sugar maples.
Official information about Great Barrington can be found on the town's website. The official website is www.townofgbma.gov. For direct inquiries, the Town Hall phone number is (413) 528-1619.

