About trails near Island Pond, Vermont

41 named trails lie within about 25 miles of Island Pond, covering 133 miles in total. 37 of them are tagged for hiking and 9 for mountain biking.

The closest is Lookout Trail, about 0.1 miles away. 41 of them lie within 10 miles of town. The longest nearby is Bluff Ridge Trail, at 31.6 miles. These trails fall in Essex County and Orleans County.

What the trails near Island Pond are like

By length, 17 are under a mile, 18 run 1 to 5 miles, and 6 are 5 miles or longer. 6 are loops, ending where they start; the longest is Bluff Ridge Trail, at 31.6 miles.

Every one carries a difficulty rating: 26 easy, 14 moderate, and 1 hard. Of the 41 with measured elevation, Bluff Ridge Trail climbs the most, about 6,850 ft, and 8 gain 1,000 ft or more.

All 41 trails, nearest first

Lookout TrailHikeEssex County3.1 mi Boreal Forest TrailHikeMTBEssex County0.4 mi Main TrailHikeEssex County0.5 mi Shoreline TrailHikeEssex County0.6 mi Loggers LoopHikeEssex County0.1 mi Red PineHikeEssex County0.2 mi Wooded WalkHikeEssex County0.1 mi Up, Up and AwayHikeOrleans County0.4 mi Leadership TrailHikeOrleans County3.5 mi Town Highway 8MTBEssex County0.8 mi Tripp Hill ConnectorHikeOrleans County0.8 mi Hopkins Hill TrailHikeOrleans County1.2 mi McConnell Pond Spur RoadHikeEssex County1.8 mi Above & BeyondHikeOrleans County1.2 mi Echo Lake TrailHikeOrleans County5.8 mi Telegraph TrailHikeOrleans County3.2 mi Mad Brook TrailHikeOrleans County5.0 mi Long Pond TrailHikeOrleans County7.7 mi Bluff Ridge TrailHikeEssex County31.6 mi Unknown Pond TrailHikeEssex County2.3 mi Spigot RoadHikeMTBEssex County1.6 mi Lepine Camp RoadHikeEssex County1.8 mi Middle Mountain TrailHikeEssex County16.1 mi Grass PathHikeOrleans County0.3 mi Gore Mountain East TrailHikeEssex County4.7 mi Moose Bog TrailHikeEssex County0.8 mi Gore Mountain TrailHikeEssex County7.7 mi Mark's RoadHikeEssex County3.7 mi Peanut Dam RoadHikeMTBEssex County1.4 mi West RoadHikeOrleans County1.6 mi Black Branch RoadHikeMTBEssex County2.4 mi East RoadHikeEssex County3.1 mi Lower Tin Shack RoadHikeMTBEssex County0.7 mi Nulhegan River TrailHikeEssex County0.9 mi Power Line Access RoadHikeMTBEssex County1.3 mi Powerline Spur #3HikeMTBEssex County0.3 mi Notch Pond TrailEssex County0.6 mi Tin Shack RoadMTBEssex County0.7 mi Power Line RoadHikeEssex County7.3 mi Morrow TrailEssex County0.7 mi North RoadHikeEssex County4.7 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 25, 2026.