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Best trails in Woodbury

327 Reviews
Looking for a great trail near Woodbury, Connecticut? AllTrails has 8 great hiking trails, trail running 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. Just looking to take a quick stroll? We've got 6 easy trails in Woodbury ranging from 0.7 to 4.6 miles and from 308 to 902 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 Woodbury
Top trails (8)
#1 - Whittemore Sanctuary
Woodbury, Connecticut
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(146)
Length: 3.7 mi • Est. 1 h 51 m
This trail is the full circumference of the Whittemore Sanctuary, though shorter and longer hikes are possible via the network of trails that cross throughout the park. With maps at nearly every trail intersection, its hard to get lost! Beautiful, wooded, and with varying terrain, the park has a lot of low, swampy areas that do tend to bring out a lot of files/gnats/mosquitos in the warmer months. There is a "bog" in the center of the park, which includes a hut on an overlook with windows facing towards it, intended for birding viewing and photography.Show more
#2 - Woodbury Trolley Trail
Trolley Bed Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(56)
Length: 3.7 mi • Est. 1 h 44 m
#3 - Orenaug Park Trail
Woodbury, Connecticut
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(49)
Length: 1.1 mi • Est. 36 m
#4 - Orenaug Park Fire Tower
Woodbury, Connecticut
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(30)
Length: 0.9 mi • Est. 30 m
#5 - Red Farm Loop
Good Hill Farm Preserve
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(13)
Length: 0.7 mi • Est. 20 m
#6 - Good Hill Brook
Woodbury, Connecticut
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(16)
Length: 4.6 mi • Est. 2 h 17 m
#7 - Van Vleck Outer Loop
Van Vleck Farm and Nature Sanctuary
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(7)
Length: 2.2 mi • Est. 53 m
This route is easy and combines multiple sanctuary trails. There are many other different trails to shorten or lengthen your visit. Trails explore forest, meadows, brooks, and ponds.Show more
#8 - Trolley CV via Trolley Trail
Trolley Bed Preserve
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow Star(1)
Length: 1.2 mi • Est. 28 m
The Trolley CV Trail is mainly a single track trail crossing the northern hillside of the Trolley Bed Preserve in Woodbury, CT. This point-to-point side trail connects the lower Trolley Bed with the eastern section of the Woodbury Reservoir. The trail allows the hiker/biker to create a loop from the main out and back Trolley Bed Trail. The Trolley CV Trail follows an old road (not in use for many years) that crossed the hillside Show more