Massachusetts · MA

Trails Near Chester

28 named trails within about 25 miles of Chester, Massachusetts, nearest first — with maps, distances, and elevation profiles.

28
Named trails
27.9 mi
Total length
28
Hiking
Map of Massachusetts with Berkshire County highlighted

About trails near Chester, Massachusetts

28 named trails lie within about 25 miles of Chester, covering 27.9 miles in total. 28 of them are tagged for hiking.

The closest is Gobble mountain trail, about 0.2 miles away. 25 of them lie within 10 miles of town. The longest nearby is Huckleberry Trolley Line, at 8.1 miles. These trails fall in Hampden County, Berkshire County, and Hampshire County.

What the trails near Chester are like

By length, 20 are under a mile, 7 run 1 to 5 miles, and 1 is 5 miles or longer.

Of the 28 with measured elevation, Gobble mountain trail climbs the most, about 1,031 ft.

All 28 trails, nearest first

Gobble mountain trailHikeHampden County1.3 miTrail of LedgesHikeHampden County0.8 miUkamit's PathHikeHampden County0.7 miBoston and Albany RailroadHikeBerkshire County0.3 miKeystone Arch Bridges TrailHikeHampshire County1.7 miPontoosuc TurnpikeHikeHampshire County1.4 miMossy Bottom TrailHikeBerkshire County0.6 miBecket Historic Quarry and Forest TrailHikeBerkshire County0.5 miLaurel Knob TrailHikeBerkshire County0.8 miFounders LoopHikeBerkshire County0.5 miFinn TrailHikeBerkshire County0.3 miThe Heights TrailHikeBerkshire County0.5 miEratic TrailHikeBerkshire County0.2 miOld Motion LoopHikeBerkshire County0.8 miGlendale Falls PathHikeHampshire County0.1 miHuckleberry Trolley LineHikeHampden County8.1 miEsau’s Heel TrailHikeBerkshire County1.3 miBeaver GlideHikeBerkshire County0.5 miSpruceHikeBerkshire County0.2 miFactory Brook Loop TrailHikeHampshire County1.9 miFuller Brook TrailHikeHampshire County1.5 miGarnet Hill TrailHikeBerkshire County0.5 miSkid RoadHikeBerkshire County0.1 miBrookside TrailHikeHampshire County0.5 miNancy Weiss TrailHikeHampshire County0.5 miSugarbush TrailHikeHampshire County1.0 miRivulet TrailHikeHampshire County0.9 miPine LoopHikeHampshire County0.3 mi

Browse by county

Hampden County
295 trails
Berkshire County
538 trails
Hampshire County
349 trails
← All of Massachusetts

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