About trails near Chimney Hill, Vermont

32 named trails lie within about 25 miles of Chimney Hill, covering 57.2 miles in total. 25 of them are tagged for hiking and 10 for mountain biking.

The closest is Hoot Toot & Whistle Trail, about 0.1 miles away. 32 of them lie within 10 miles of town. The longest nearby is Catamount Trail Section 4, at 9.9 miles. These trails fall in Windham County and Bennington County.

All 32 trails, nearest first

Hoot Toot & Whistle TrailHikeWindham County1.9 mi Haystack Mountain TrailHikeWindham County2.0 mi Forest Road 268HikeBennington County2.1 mi Valley TrailHikeWindham County6.1 mi Tunnel TrailWindham County0.5 mi The Inn TrailWindham County0.6 mi East Branch TrailHikeBennington County1.0 mi Little John TrailHikeWindham County1.7 mi Sherwood Forest TrailHikeWindham County0.5 mi Catamount TrailHikeBennington County7.6 mi Flood Dam TrailHikeBennington County2.8 mi Crosstown TrailHikeMTBWindham County1.0 mi Deerfield Ridge TrailHikeWindham County3.7 mi Bears Crossing Ski Home TrailWindham County1.0 mi SweetHikeWindham County0.3 mi Play NiceHikeMTBWindham County0.9 mi Grade AHikeWindham County0.2 mi Cannonball RunMTBWindham County0.2 mi Wide OpenMTBWindham County0.5 mi SugarhouseHikeWindham County0.2 mi Earle Farm RoadHikeWindham County0.4 mi The Way InHikeWindham County0.2 mi Sap BucketHikeMTBWindham County0.2 mi Spruce LoopHikeMTBWindham County0.2 mi High TraverseWindham County0.4 mi Low TraverseWindham County0.8 mi Hathaway TrailHikeWindham County0.9 mi Forest Road 376HikeMTBBennington County0.8 mi Forest Road 324HikeMTBWindham County0.8 mi Catamount Trail Section 4HikeWindham County9.9 mi Castle Brook RoadHikeMTBBennington County6.1 mi Flood Dam RoadHikeMTBWindham County1.3 mi

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Trail geometry from OpenStreetMap contributors, licensed ODbL. Elevation from the USGS 3D Elevation Program. Compiled and published by Trailmonger · trail data last rebuilt August 29, 2026.