Trails Near Canaan, MA | Trailmonger

About trails near Canaan, Massachusetts

19 named trails lie within about 25 miles of Canaan, covering 18.0 miles in total. 19 of them are tagged for hiking and 1 for mountain biking.

The closest is Bailey Trail, about 0.2 miles away. 19 of them lie within 10 miles of town. The longest nearby is Blue Trail, at 4.9 miles. These trails fall in Berkshire County.

All 19 trails, nearest first

Bailey TrailHikeBerkshire County1.2 mi Tulip Tree TrailHikeBerkshire County0.6 mi Craggy Knoll TrailHikeBerkshire County0.2 mi Cedar Hill TrailHikeBerkshire County0.1 mi Ledges TrailHikeBerkshire County0.5 mi Tractor PathHikeBerkshire County0.7 mi Eaton TrailHikeBerkshire County0.1 mi Main Outer LoopHikeBerkshire County0.9 mi Hal Borland TrailHikeBerkshire County0.6 mi Orchard TrailHikeBerkshire County0.6 mi Quarry TrailHikeBerkshire County0.4 mi Lime Kiln LoopHikeBerkshire County0.6 mi Taconic Vista TrailHikeBerkshire County0.3 mi Drury TrailHikeBerkshire County1.3 mi Deborah Reich TrailHikeBerkshire County0.6 mi Blue TrailHikeMTBBerkshire County4.9 mi Lower Falls TrailHikeBerkshire County0.3 mi Yellow TrailHikeBerkshire County2.1 mi Race Brook TrailHikeBerkshire County1.9 mi

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Berkshire County

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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.