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Best trails in Upton

736 Reviews
Explore the most popular trails near Upton with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
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Map of trails in Upton
Top trails (4)
#1 - Peppercorn Hill
Upton, Massachusetts
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Length: 2.5 mi • Est. 1 h 14 m
Climbs sharply to 500 foot summit of Peppercorn Hill.Show more
#2 - White Hall Road and Park Road Loop
Upton State Forest
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Length: 3.8 mi • Est. 1 h 45 m
#3 - Loop, Park and Den Pond Road Loop
Upton State Forest
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Length: 3.3 mi • Est. 1 h 30 m
A slightly more rustic and less traveled path in the Upton State Forest. Loop Rd. is a wide easily traveled path through the woods that leads to Whistling Cave path. Whistling Cave path is much less traveled and more challenging with a number of small streams to cross and large rock formations (including Whistling Cave).Show more
#4 - Whistling Cave and Nuthatch Loop
Upton, Massachusetts
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Length: 4.1 mi • Est. 1 h 56 m