Best trails in Great Barrington

576 Reviews
Looking for a great trail near Great Barrington, Massachusetts? AllTrails has 16 great hiking trails, running trails, forest trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Mount Riga State Park or Talcott Mountain State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Mount Everett State Reservation. Ready for some activity? There are 8 moderate trails in Great Barrington ranging from 2 to 9.3 miles and from 744 to 2,011 feet above sea level. Start checking them out and you'll be out on the trail in no time!
Show more
Map of trails in Great Barrington
Top trails (16)
#1 - Appalachian Trail from Jug End to Bear Mountain
Jug End State Reservation & Wildlife Management Area
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(54)
Length: 10.4 mi • Est. 6 h 33 m
Appalachian Trail from Jug End to Bear Mountain is a 10.4 mile moderately trafficked point-to-point trail located near Great Barrington, Massachusetts that features a lake and is only recommended for Show more
#2 - Benedict Pond Loop Trail
Beartown State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(94)
Length: 1.7 mi • Est. 46 m
Benedict Pond Loop Trail is a 1.7 mile moderately trafficked loop trail located near Great Barrington, Massachusetts that features a lake and is good for all skill levels. The trail offers a number ofShow more
#3 - East Mountain via Appalachian Trail
East Mountain State Forest
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(38)
Length: 8.9 mi • Est. 4 h 54 m
East Mountain via Appalachian Trail is a 8.9 mile moderately trafficked out and back trail located near Great Barrington, Massachusetts that features beautiful wild flowers and is rated as difficult. Show more
#4 - Mt. Wilcox and Beartown Mountain Trail Loop
Beartown State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(47)
Length: 9.3 mi • Est. 4 h 28 m
From the NE part of the parking lot take the loop trail that connects to the Appalachian Trail. Take the AT in the N direction (white blazed trail). Continuing on the AT, just before crossing a brookShow more
#5 - Alford Springs Reservation
Alford Spring Wildlife Conservation Easement
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(74)
Length: 4.3 mi • Est. 2 h 16 m
Alford Springs Reservation is a 4.3 mile lightly trafficked loop trail located near Great Barrington, Massachusetts that features a great forest setting and is rated as moderate. The trail offers a nuShow more
#6 - Benedict Pond and The Ledges
Beartown State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(38)
Length: 4.1 mi • Est. 1 h 58 m
Park at the Benedict Pond lot (fees payable at certain times of year). Go counter-clockwise on the Benedict Pond Loop Trail (blue blazes) and follow it to the South Eastern end of the lake and then arShow more
#7 - Appalachian Trail: Beartown to Bald Top
Beartown State Forest
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(12)
Length: 22.9 mi • Est. 11 h 55 m
Appalachian Trail: Beartown to Bald Top is a 22.9 mile moderately trafficked point-to-point trail located near Great Barrington, Massachusetts that features a great forest setting and is only recommenShow more
#8 - Threemile Hill Trail at Fountain Pond
Fountain Pond Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(21)
Length: 3.9 mi • Est. 2 h 1 m
Threemile Hill Trail at Fountain Pond is a 3.9 mile lightly trafficked out and back trail located near Great Barrington, Massachusetts that features a lake and is rated as moderate. The trail is primaShow more
#9 - Dry Hill
Sandisfield State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(18)
Length: 2 mi • Est. 58 m
Dry Hill is a 2 mile out and back trail located near Great Barrington, Massachusetts that offers scenic views and is rated as moderate. The trail is primarily used for hiking and is accessible year-roShow more
#10 - Benedict Pond Loop and AT to Monterey Road
Beartown State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(14)
Length: 5.2 mi • Est. 2 h 44 m
From the parking lot near Benedict Pond beach (fees applicable in Summer), head South East on the Blue-blazed Pond Loop trail, keeping the pond to your left. After about 4/10 of a mile, you'll see a NShow more
Showing results 1 - 10 of 16