Trails Near Freeport, ME | Trailmonger

About trails near Freeport, Maine

59 named trails lie within about 25 miles of Freeport, covering 44.2 miles in total. 59 of them are tagged for hiking and 22 for mountain biking.

The closest is Orchard Trail, about 0.2 miles away. 59 of them lie within 10 miles of town. The longest nearby is Lake Loop Trail, at 4.2 miles. These trails fall in Cumberland County.

What the trails near Freeport are like

By length, 47 are under a mile and 12 run 1 to 5 miles. 2 are loops, ending where they start; the longest is Island, at 1.2 miles.

Of the 21 with a difficulty rating, 7 easy and 14 moderate. Of the 56 with measured elevation, North Loop Trail climbs the most, about 367 ft.

All 59 trails, nearest first

Orchard TrailHikeMTBCumberland County0.3 mi Link Trail IHikeCumberland County0.1 mi Bench Loop TrailHikeCumberland County0.2 mi Deer Run TrailHikeCumberland County0.3 mi Mill Stream TrailHikeCumberland County0.5 mi Link Trail 2HikeCumberland County0.2 mi Ridge TrailHikeCumberland County1.5 mi Senior Project TrailHikeMTBCumberland County0.4 mi Wentworth TrailHikeMTBCumberland County0.2 mi Soule RoadHikeMTBCumberland County0.4 mi Stonewall TrailHikeMTBCumberland County0.2 mi Reed RoadHikeMTBCumberland County0.1 mi Upper ConnectorHikeMTBCumberland County0.2 mi Summit TrailHikeMTBCumberland County0.7 mi Hedgehog TrailHikeMTBCumberland County0.3 mi Stonewood TrailHikeCumberland County0.6 mi Sayles FieldHikeCumberland County1.1 mi Little Bridge TrailHikeMTBCumberland County0.4 mi Keith LoopHikeMTBCumberland County0.8 mi Edge TrailHikeMTBCumberland County0.3 mi The PathHikeCumberland County0.1 mi Mitchell Ledge TrailHikeCumberland County0.7 mi Big Loop TrailHikeMTBCumberland County1.2 mi Kelsey Brook TrailHikeCumberland County1.2 mi Little River Loop TrailHikeCumberland County0.8 mi Harraseeket TrailHikeCumberland County1.4 mi Brewer Woods TrailHikeCumberland County0.4 mi Discovery TrailHikeCumberland County0.3 mi Farm Loop TrailHikeCumberland County1.5 mi Simpson Woods White TrailHikeCumberland County0.8 mi Whippoorwill Woods TrailHikeCumberland County0.7 mi Gibby's TrailHikeCumberland County0.8 mi Power Line TrailHikeCumberland County0.3 mi Hemlock Ridge TrailHikeCumberland County0.2 mi Old Woods Road TrailHikeCumberland County0.3 mi Simpson Woods Blue TrailHikeCumberland County0.9 mi Lake Loop TrailHikeCumberland County4.2 mi Ledge TrailHikeCumberland County0.2 mi Casco Bay TrailHikeCumberland County0.2 mi White Pines TrailHikeCumberland County0.7 mi Brimstone Hill TrailHikeCumberland County0.6 mi Tadpole TrailHikeCumberland County0.9 mi North Loop TrailHikeCumberland County4.1 mi Moose Crossing TrailHikeCumberland County0.4 mi Antoinette Jackman TrailHikeCumberland County0.5 mi Hidden Pond TrailHikeCumberland County0.4 mi Fox EastHikeMTBCumberland County1.1 mi Fox CutoffHikeCumberland County0.2 mi Hamshah SpecialHikeCumberland County0.2 mi Fox By-PassHikeMTBCumberland County0.2 mi Snowmobile TrailHikeMTBCumberland County2.9 mi BatcaveHikeMTBCumberland County0.7 mi FernHikeCumberland County0.3 mi GinnHikeMTBCumberland County2.1 mi Old Tuttle RoadHikeCumberland County0.3 mi Fox WestHikeMTBCumberland County0.8 mi RaganHikeMTBCumberland County0.9 mi LanzoHikeMTBCumberland County0.6 mi IslandHikeMTBCumberland County1.2 mi

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Cumberland 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.