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Best trails in Bolton

379 Reviews
Looking for a great trail near Bolton, Massachusetts? AllTrails has 9 great hiking trails, walking trails, kid friendly 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 Monadnock State Park or Whitehall State Park, we've got you covered. You'll also find some great local park options, like Blue Hills Reservation or Watatic Mountain State Wildlife Area. Just looking to take a quick stroll? We've got 8 easy trails in Bolton ranging from 0.7 to 3.2 miles and from 269 to 547 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 Bolton
Top trails (9)
#1 - Vaughn Hills Trail
Vaughn Hills Conservation Area
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(100)
Length: 2.8 mi • Est. 1 h 22 m
A lovely afternoon hike. The variability in the terrain makes this hike a little more interesting and fun. There is some climbing over rocks towards the top, but nothing difficult. The pond is interesShow more
#2 - Bolton Lime Quarry and Kiln Loop
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(93)
Length: 2.4 mi • Est. 1 h 9 m
Bolton Lime Quarry and Kiln Loop is a 2.4 mile moderately trafficked loop trail located near Bolton, Massachusetts that features a river and is good for all skill levels. The trail offers a number of Show more
#3 - Bowers Spring and Bare Hill Trail
Vaughn Hills Conservation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(43)
Length: 3.2 mi • Est. 1 h 27 m
This is a level and leisurely hike. The area around the ponds is a popular destination for dogs. There is also a lot of beaver activity along this area.Show more
#4 - Bowers Spring Trail
Vaughn Hills Conservation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(52)
Length: 0.8 mi • Est. 22 m
Bowers Spring Trail is a 0.8 mile lightly trafficked loop trail located near Bolton, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a number of aShow more
#5 - Rattle Snake Trail
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(39)
Length: 2.2 mi • Est. 1 h 2 m
Rattle Snake Trail is a 2.2 mile moderately trafficked loop trail located near Bolton, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a number ofShow more
#6 - Harris Farms Trail to Rattle Snake Hill Trail
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(21)
Length: 2 mi • Est. 57 m
Harris Farms Trail to Rattle Snake Hill Trail is a 2 mile moderately trafficked loop trail located near Bolton, Massachusetts that features a cave and is good for all skill levels. The trail offers a Show more
#7 - Bob Horton Trail
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(5)
Length: 1.1 mi • Est. 31 m
Bob Horton Trail is a 1.1 mile moderately trafficked loop trail located near Bolton, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a number of aShow more
#8 - Split Rock Trail
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(22)
Length: 1.5 mi • Est. 42 m
Split Rock Trail is a 1.5 mile moderately trafficked loop trail located near Bolton, Massachusetts that features a great forest setting and is good for all skill levels. The trail offers a number of aShow more
#9 - Fyfeshire Conservation Area Trail
Bolton, Massachusetts
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(6)
Length: 0.7 mi • Est. 17 m
Fyfeshire Conservation Area Trail is a 0.7 mile lightly trafficked out and back trail located near Bolton, Massachusetts that features a great forest setting and is good for all skill levels. The traiShow more