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Best trails in New Fairfield

437 Reviews
Looking for a great trail near New Fairfield, Connecticut? AllTrails has 7 great hiking trails, trail 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 Bear Mountain State Park or Hudson Highlands State Park Preserve, we've got you covered. You'll also find some great local park options, like Mount Beacon Park or Mine Hill Preserve. Just looking to take a quick stroll? We've got 4 easy trails in New Fairfield ranging from 1.1 to 2.4 miles and from 456 to 1,187 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 New Fairfield
Top trails (7)
#1 - Squantz Pond Trail
Squantz Pond State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(161)
Length: 2.2 mi • Est. 1 h 6 m
Squantz Pond immerses the visitor in a "mountain like" setting. Steep, wooded slopes disappear into the cool, blue pond below. In the fall, the park becomes a haven for photographers capturing the colShow more
#2 - Great Hollow Main Loop
Great Hollow Nature Preserve & Ecological Research Center
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(101)
Length: 2.4 mi • Est. 1 h 10 m
Great Hollow Main Loop is a 2.4 mile moderately trafficked loop trail located near New Fairfield, Connecticut that features a waterfall and is good for all skill levels. The trail offers a number of aShow more
#3 - Pootatuck State Forest Loop
Pootatuck State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(85)
Length: 2 mi • Est. 49 m
Hilly terrain with great features. Pootatuck State Forest is almost 1,200 acres. It is located primarily in New Fairfield, with a small portion in Sherman. The main block of the Forest rises steeply Show more
#4 - Great Hollow and Lower Overlook Loop
Great Hollow Nature Preserve & Ecological Research Center
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(40)
Length: 4 mi • Est. 2 h 9 m
Great Hollow and Lower Overlook Loop is a 4 mile loop trail located near New Fairfield, Connecticut that features a river and is rated as moderate. The trail is primarily used for hiking, walking, traShow more
#5 - Sweetcake Mountain via White Trail
Sweetcake Mountain Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(22)
Length: 1.1 mi • Est. 37 m
Sweetcake Mountain via White Trail is a 1.1 mile loop trail located near New Fairfield, Connecticut that offers the chance to see wildlife and is good for all skill levels. The trail is primarily usedShow more
#6 - Pine Hill Road Loop
Pootatuck State Forest
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(22)
Length: 1.9 mi • Est. 58 m
Pine Hill Road Loop is a 1.9 mile moderately trafficked loop trail located near New Fairfield, Connecticut that features beautiful wild flowers and is good for all skill levels. The trail offers a numShow more
#7 - Pine Hill to Squantz Pond
Squantz Pond State Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray StarGray StarGray Star(6)
Length: 4.6 mi • Est. 1 h 51 m
This route starts at the top of Pine Hill Road and ends at the lower parking lot of Squantz Pond State Park. You can return back up the hill on the trails or stay at the Squantz Pond. Squantz Pond StaShow more