Trails Near Milford, MA | Trailmonger

About trails near Milford, Massachusetts

72 named trails lie within about 25 miles of Milford, covering 33.6 miles in total. 69 of them are tagged for hiking and 44 for mountain biking.

The closest is Nemba Loop, about 0.0 miles away. 72 of them lie within 10 miles of town. The longest nearby is Upper Charles Trail, at 7.1 miles. These trails fall in Worcester County and Middlesex County.

What the trails near Milford are like

By length, 70 are under a mile, 1 runs 1 to 5 miles, and 1 is 5 miles or longer. 1 is a loop, ending where it starts; the longest is Dirty Little Secret, at 0.9 miles.

Of the 43 with a difficulty rating, 3 easy and 40 moderate. Of the 72 with measured elevation, Pipeline Trail climbs the most, about 561 ft.

All 72 trails, nearest first

Nemba LoopHikeMTBWorcester County0.7 mi C4HikeMTBWorcester County0.2 mi Soaring EagleHikeWorcester County0.2 mi Eagle's NestHikeWorcester County0.3 mi Don't Ask, Don't TellHikeWorcester County0.2 mi Rib BreakerHikeMTBWorcester County0.1 mi Rib ShakerHikeMTBWorcester County0.2 mi Dirty Little SecretMTBWorcester County0.9 mi Rubber StampHikeMTBWorcester County0.2 mi Lost TrailHikeMTBWorcester County0.2 mi Down and UpHikeMTBWorcester County0.4 mi VaritekHikeWorcester County0.2 mi NEMBA WayHikeMTBWorcester County0.2 mi The Parklands Purple TrailHikeMTBWorcester County0.3 mi Linkin' LogsHikeMTBWorcester County0.2 mi LeftoversHikeWorcester County0.4 mi KitchenHikeMTBWorcester County0.6 mi Mind The GapHikeWorcester County0.1 mi Three LedgesHikeWorcester County0.3 mi One LedgesHikeWorcester County0.2 mi Lower Three LedgesHikeMTBMiddlesex County0.2 mi 50 Yards the Hard WayHikeWorcester County0.2 mi GiggidyHikeWorcester County0.3 mi The Main TrailHikeMTBMiddlesex County0.6 mi Fairbank TrailHikeMTBMiddlesex County0.2 mi Burnt EndsHikeWorcester County0.3 mi Number 5HikeMTBMiddlesex County0.1 mi The GigHikeWorcester County0.2 mi Uphill ConnectorHikeWorcester County0.1 mi Knee JerkHikeMTBMiddlesex County0.4 mi "B" BypassHikeWorcester County0.1 mi Teetering Rock TrailHikeMTBMiddlesex County0.3 mi Fairbanks TrailHikeMTBMiddlesex County0.2 mi Three SistersHikeMTBMiddlesex County0.4 mi Condo RockHikeWorcester County0.1 mi Swamp SideHikeMiddlesex County0.3 mi Swamp BypassHikeMTBMiddlesex County0.6 mi Toe JamHikeMTBMiddlesex County0.2 mi Chattering Rock WayHikeMTBMiddlesex County0.2 mi Middle SisterHikeMTBMiddlesex County0.6 mi NEMBA TrailHikeMTBWorcester County0.4 mi Pipeline TrailHikeWorcester County3.2 mi TontoHikeMTBMiddlesex County0.3 mi Holliston HighwayHikeMTBMiddlesex County0.9 mi Deer WayHikeMTBMiddlesex County0.2 mi Highway ConnectorHikeMTBWorcester County0.2 mi Hob KnobHikeMTBWorcester County0.4 mi Milford BywayMTBMiddlesex County0.5 mi Burial By-passHikeMTBMiddlesex County0.9 mi Sudden ImpactHikeMTBMiddlesex County0.3 mi New TrailHikeMTBMiddlesex County0.5 mi Log RunHikeMTBMiddlesex County0.3 mi KrusherHikeMiddlesex County0.4 mi Bumble BeeHikeMiddlesex County0.1 mi Right Turn ClydeHikeMTBMiddlesex County0.6 mi Beaver Brook WayHikeMTBMiddlesex County0.5 mi Battle ScarHikeMiddlesex County0.2 mi The GulleyHikeMTBMiddlesex County0.3 mi Dennis' PlaygroundHikeMiddlesex County0.4 mi Walleston TrailHikeMTBWorcester County0.7 mi UberbermHikeMiddlesex County0.2 mi North StarHikeMiddlesex County0.1 mi Roller CoasterHikeMiddlesex County0.1 mi The Road Less TraveledHikeWorcester County0.5 mi Upper Charles TrailMTBMiddlesex County7.1 mi CliffwalkHikeMiddlesex County0.1 mi The IntroHikeMTBMiddlesex County0.4 mi It Wasn't MeHikeMiddlesex County0.2 mi Rockwood Meadows TrailHikeMiddlesex County0.3 mi College Rock RunHikeMTBMiddlesex County0.5 mi Purple DiamondHikeMTBMiddlesex County0.5 mi High Water BypassHikeMTBMiddlesex County0.3 mi

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Worcester County

Middlesex 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 October 4, 2026.