About trails in Dukes County, Massachusetts

Dukes County has 140 named trails on the map, covering 104 miles in total, an average of 0.7 miles per trail. That is the 12th largest mapped trail network among 14 counties in Massachusetts. 137 of them are tagged for hiking and 14 for mountain biking.

The longest single trail is State Forest Bike Path, at 12.1 miles. 1 trail runs 5 miles or longer. Mapped points of interest in the county include 8 trailheads, 4 campsites, and 8 boat launches. The nearest towns to these trails are Vineyard Haven, Edgartown, and Oak Bluffs.

What the trails in Dukes County are like

By length, 112 are under a mile, 27 run 1 to 5 miles, and 1 is 5 miles or longer. 4 are loops, ending where they start; the longest is Greenlands Inner Loop, at 2.3 miles.

Of the 140 with measured elevation, Orange Trail climbs the most, about 189 ft.

Explore by activity

104Total miles

4Campsites

8Boat launches

8Trailheads

State Forest Bike PathHikeMTB12.1 mi X Chappy (North Neck to Wasque)Hike4.0 mi Katama Road PathwayHike2.6 mi Dr. Fisher RoadHike2.4 mi Greenlands Inner LoopHike2.3 mi Herring Creek Road Pathway2.1 mi Nor'easter (North)Hike1.9 mi Pocketapaces TrailHike1.8 mi Old Holmes Hole RoadHike1.7 mi Red Trail (East)Hike1.7 mi Rich's RideHikeMTB1.6 mi Fire Road 5HikeMTB1.6 mi Booming Ben TrailHike1.6 mi Green TrailHike1.6 mi Nashawakemuck LoopHike1.5 mi Fire Road 4HikeMTB1.4 mi Purple TrailHike1.4 mi Doctor Fisher Road - Fire Road BHikeMTB1.4 mi Middle Line w/ detourHike1.4 mi Pennywise Preserve N/S ConnectorHike1.3 mi Fire Road 2HikeMTB1.3 mi White TrailHike1.2 mi Woods LoopHike1.1 mi Doctor Fisher RoadHikeMTB1.1 mi Yellow TrailHike1.1 mi Orange TrailHike1.1 mi Quampache TrailHike1.0 mi Gay Head Moraine woodland trailHike1.0 mi Beach TrailHike1.0 mi Nor'easter (East)Hike0.9 mi Ben Luce Path - Fire Road 7HikeMTB0.9 mi Ripley's Field PathHike0.9 mi Deep Bottom Path (North(Hike0.9 mi Checamo RoadHikeMTB0.9 mi Harris LoopHike0.9 mi Middle Road Sactuary Trail - YellowHike0.9 mi Red Trail (Middle)Hike0.8 mi Holman PathHike0.8 mi Bottom TrailHike0.8 mi Fire Road 1HikeMTB0.8 mi Deep Bottom Path (South)Hike0.8 mi Pennywise PathHike0.8 mi Road to Farm NeckHike0.8 mi Stoney Hill PathHike0.7 mi Sailors Burying Ground RoadHike0.7 mi Pine TrailHike0.7 mi Willow TreeHike0.7 mi David H Smith PreserveHike0.6 mi Quampache Trail (North)Hike0.6 mi Phillips Reserve Red Blue TrailHike0.6 mi Marsh TrailHike0.6 mi West End TrailHike0.6 mi Middle Road Sactuary Trail - RedHike0.6 mi Sassafras TrailHike0.6 mi Little Pond RoadHike0.6 mi Brickyard TrailHike0.6 mi WCW Red TrailHike0.6 mi Slater PreserveHike0.6 mi Old Farm RoadHike0.6 mi Jessica Hancock Memorial TrailHike0.6 mi Fire Road BHikeMTB0.5 mi Blue TrailHike0.5 mi Road to WapatequaHike0.5 mi Whip-Poor-Will WayHike0.5 mi EC TPR 16 (Yellow)Hike0.5 mi Forest SidewinderHike0.5 mi Margaret S. Lindsay Memorial TrailHike0.5 mi Shoreline TrailHike0.5 mi WCW Green TrailHike0.5 mi WestboundHike0.5 mi Southern Loop Connector0.5 mi The Last TrailHike0.5 mi MCP-BlueHike0.5 mi Huckleberry Barrens TrailHike0.5 mi Pocha Pond LoopHike0.5 mi Purple-Red TrailHike0.5 mi Moshup Beach TrailHike0.5 mi Packard PreserveHike0.5 mi Fire Road EHikeMTB0.5 mi Ames PreserveHike0.5 mi Log JamHike0.4 mi Nat's Farm TrailHike0.4 mi Manaquayak Preserve TrailHike0.4 mi WCW Blue TrailHike0.4 mi Red Trail (West)Hike0.4 mi Red TrailHike0.4 mi Public Walking PathHike0.4 mi Brown TrailHike0.4 mi Nor'easter (West)Hike0.4 mi Greenlands to Wapatequa ConnectorHike0.4 mi North Head LoopHike0.4 mi Ancient WayHike0.4 mi WCW Yellow TrailHike0.4 mi Tiahs Cove RoadHike0.3 mi Chase RoadHike0.3 mi Middle Road Sactuary Trail - GreenHike0.3 mi Eachpoquassit Hill Preserve TrailHike0.3 mi Bruce Irons TrailHike0.3 mi Tar KilnHike0.3 mi Ramble TrailHike0.3 mi Swimming Place PathHike0.3 mi MCP-YellowHike0.3 mi Orange White TrailHike0.3 mi Three Ponds ReservationHike0.3 mi MCP-PurpleHike0.3 mi Loop to School HouseHike0.2 mi Field LoopHike0.2 mi Little Pond Fire RoadHikeMTB0.2 mi Red Coat Hill RoadHike0.2 mi From AboveHike0.2 mi Middle Road Sactuary Trail - PurpleHike0.2 mi Orange Blue TrailHike0.2 mi Katama Bay TrailHike0.2 mi Edgartown Great Pond TrailHike0.2 mi Maria Daggett TrailHike0.2 mi Pond Loop0.2 mi White Blue TrailHike0.2 mi Close ConnectorHike0.2 mi Chappaquiddick TrailHike0.2 mi Chappaquonsett TrailHike0.2 mi Ridge TrailHike0.2 mi MCP-RedHike0.2 mi Barnes ParallelHike0.2 mi Farm Road ConnectorHike0.2 mi The Back TrailHike0.2 mi PowerlinesHike0.1 mi Quampache LoopHike0.1 mi Middle Road Sactuary Trail - WhiteHike0.1 mi Healthland Meander ConnectorHike0.1 mi Phillips Reserve Blue TrailHike0.1 mi Nor'easter BailoutHike0.1 mi Shad TrailHike0.1 mi Neighborhood TrailHike0.1 mi Whip-Poor-Will Way ConnectorHike0.1 mi Middle Road Sactuary Trail - BlueHike0.1 mi Manter Field TrailHike0.1 mi Dr. Fisher Road to Fire Road B (East)Hike0.1 mi Bittersweet TrailHike0.1 mi Abandoned SingletrackHike0.1 mi Fire Tower Road (Hole 10 Red)HikeMTB0.1 mi

Trails by town in Dukes County

More Massachusetts counties

1,339 trails · 1,542 mi

Worcester County

990 trails · 1,017 mi

Norfolk County

378 trails · 325 mi

← 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 September 24, 2026.