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Best trails in Williamstown

1007 Reviews
Looking for a great trail near Williamstown, Massachusetts? AllTrails has 22 great hiking trails, trail running trails, views 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 Peebles Island State Park or Grafton Lakes State Park, we've got you covered. You'll also find some great local park options, like Mount Greylock State Reservation or Walnut Hill Wildlife Management Area. Ready for some activity? There are 11 moderate trails in Williamstown ranging from 2.4 to 4.9 miles and from 682 to 3,467 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Williamstown
Top trails (22)
#1 - Mount Williams, Mount Fitch, Mount Greylock, and Stony Ledge
Mount Greylock State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(191)
Length: 12.4 mi • Est. 7 h 2 m
This is a beautiful hike that starts along Money Brook and follows it to a waterfall. It's one of the best hikes in the Berkshire region because it features the tallest mountain in Massachusetts. It Show more
#2 - Pine Cobble Trail
Clarksburg State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(159)
Length: 3.3 mi • Est. 2 h 8 m
Pine Cobble Trail is a 3.3 mile heavily trafficked out and back trail located near Williamstown, Massachusetts that features a river and is rated as moderate. The trail is primarily used for hiking anShow more
#3 - Mount Greylock Overlook Trail
Mount Greylock State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(92)
Length: 2.4 mi • Est. 1 h 24 m
Overlook Trail can be considered primarily a connector trail between the Hopper Trail and the Summit of Mt. Greylock. It offers one scenic vista with limited views and easy to moderate terrain. BeginShow more
#4 - The Hopper Trail
Mount Greylock State Reservation
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(110)
Length: 4.8 mi • Est. 2 h 49 m
The Hopper Trail begins on Hopper Rd. in Williamstown, MA and climbs gradually and at times very steeply through old forest growth to Sperry Rd and then up to the Mt. Greylock Summit. The Hopper TraiShow more
#5 - Stony Ledge Trail
Mount Greylock State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(48)
Length: 4.2 mi • Est. 2 h 42 m
Descend from Stony Ledge (Sperry Road) down the old Stony Ledge Ski Trail (which may be accessible for skiing in the winter... google it!). Return via Stony Ledge Trail or via Roaring Brook Trail to Show more
#6 - Hopkins Memorial Forest Trail
Williamstown, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(67)
Length: 4.1 mi • Est. 2 h 4 m
Hopkins Memorial Forest Trail is a 4.1 mile moderately trafficked loop trail located near Williamstown, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail offers a Show more
#7 - Phelps Trail to the Taconic Crest Trail down the Mills Hollow Trail
Williamstown, Massachusetts
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(53)
Length: 4.3 mi • Est. 2 h 42 m
Phelps Trail to the Taconic Crest Trail down the Mills Hollow Trail is a 4.3 mile lightly trafficked loop trail located near Williamstown, Massachusetts that features a river and is rated as moderate.Show more
#8 - RRR Brooks Trail to Shepherd’s Well to Taconic Crest
Taconic Trail State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(40)
Length: 4.9 mi • Est. 2 h 39 m
RRR Brooks Trail to Shepherd’s Well to Taconic Crest is a 4.9 mile lightly trafficked out and back trail located near Williamstown, Massachusetts that features beautiful wild flowers and is rated as mShow more
#9 - Field Farm Trail
Williamstown, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(28)
Length: 2.4 mi • Est. 1 h 5 m
Field Farm Trail is a 2.4 mile moderately trafficked loop trail located near Williamstown, Massachusetts that features a great forest setting and is good for all skill levels. The trail offers a numbeShow more
#10 - Roaring Brook Trail to Deer Hill Falls
Mount Greylock State Reservation
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(30)
Length: 3.9 mi • Est. 2 h 38 m
Roaring Brook Trail to Deer Hill Falls is a 3.9 mile lightly trafficked out and back trail located near Williamstown, Massachusetts that features a waterfall and is rated as difficult. The trail is prShow more
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