About trails near Wellesley, Massachusetts

19 named trails lie within about 25 miles of Wellesley, covering 13.4 miles in total. 19 of them are tagged for hiking.

The closest is Riverside Trail, about 0.0 miles away. 19 of them lie within 10 miles of town. The longest nearby is Main Trail, at 2.0 miles. These trails fall in Norfolk County and Middlesex County.

What the trails near Wellesley are like

By length, 14 are under a mile and 5 run 1 to 5 miles. 3 are loops, ending where they start; the longest is Lower Loop Trail, at 0.8 miles.

Of the 19 with measured elevation, Glacial Hill Trail climbs the most, about 133 ft.

All 19 trails, nearest first

Riverside TrailHikeNorfolk County1.5 mi Quinobin TrailHikeNorfolk County0.1 mi Horseshoe TrailHikeNorfolk County0.2 mi Meander TrailHikeNorfolk County0.1 mi Olmstead TrailHikeNorfolk County0.2 mi Takawambpait SouthHikeMiddlesex County0.3 mi Sudbury Aqueduct PathHikeMiddlesex County0.3 mi Lower Loop TrailHikeMiddlesex County0.8 mi Takawambpait NorthHikeMiddlesex County0.6 mi Main TrailHikeMiddlesex County2.0 mi Summit TrailHikeMiddlesex County0.3 mi Mary Ann Morse PathHikeMiddlesex County0.3 mi Eisenmenger TrailHikeMiddlesex County1.9 mi Charles River LoopHikeMiddlesex County1.0 mi Boundary TrailHikeMiddlesex County0.5 mi Indian Brook TrailHikeMiddlesex County0.5 mi Glacial Hill TrailHikeMiddlesex County1.4 mi Blueberry Swamp LoopHikeMiddlesex County0.8 mi Glacial Hill LoopHikeMiddlesex County0.5 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 October 4, 2026.