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Best trails in Cheshire

787 Reviews
Looking for a great trail near Cheshire, Connecticut? AllTrails has 7 great hiking trails, forest trails, walking 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 Talcott Mountain State Park or Wadsworth Falls State Park, we've got you covered. You'll also find some great local park options, like Ragged Mountain Memorial Preserve or Hubbard Park. Ready for some activity? There are 4 moderate trails in Cheshire ranging from 1.4 to 3.6 miles and from 164 to 889 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 Cheshire
Top trails (7)
#1 - Roaring Brook Falls Trail
Hotchkiss Field
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(267)
Length: 1.4 mi • Est. 52 m
Roaring Brook Falls Trail is a 1.4 mile heavily trafficked loop trail located near Cheshire, Connecticut that features a waterfall and is rated as moderate. The trail is primarily used for hiking, runShow more
#2 - Quinnipiac Trail to Roaring Brook Falls
Naugatuck State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(131)
Length: 3.6 mi • Est. 2 h 7 m
A nice chilly walk on the Quinnipiac trail over to roaring Brook Falls.Show more
#3 - Quinnipiac Trail Loop
Naugatuck State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(170)
Length: 3.2 mi • Est. 1 h 42 m
Quinnipiac Trail Loop is a 3.2 mile heavily trafficked loop trail located near Cheshire, Connecticut that features a great forest setting and is rated as moderate. The trail offers a number of activitShow more
#4 - Roaring Brook Falls via Roaring Brook Road
Cheshire, Connecticut
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(81)
Length: 1.2 mi • Est. 44 m
Roaring Brook Falls via Roaring Brook Road is a 1.2 mile out and back trail located near Cheshire, Connecticut that features a waterfall. The trail is good for all skill levels and primarily used for Show more
#5 - Mount Sanford Loop
Naugatuck State Forest
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(46)
Length: 3.3 mi • Est. 1 h 47 m
Mount Sanford Loop is a 3.3 mile moderately trafficked loop trail located near Cheshire, Connecticut that features a great forest setting and is rated as moderate. The trail is primarily used for hikiShow more
#6 - Farmington Canal Linear State Park Trail
Farmington Canal Line State Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(84)
Length: 10.9 mi • Est. 4 h 28 m
Farmington Canal Linear State Park Trail is a 10.9 mile out and back trail located near Cheshire, Connecticut that offers scenic views and is good for all skill levels. The trail offers a number of acShow more
#7 - Casterano Open Space
Casterano Open Space
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(8)
Length: 1.6 mi • Est. 50 m
Casterano Open Space is a 1.6 mile lightly trafficked out and back trail located near Cheshire, Connecticut that features a great forest setting and is good for all skill levels. The trail is primarilShow more