Best hikes in Myles Standish State Forest
Ambleway maps 59 hikes in Myles Standish State Forest, from a 1.9-mile walk to a 16-mile day out. All of them score as wild, staying clear of roads and development for most of the route; the wildest is Webster Springs Road. The biggest climb is Russell Millpond–Crosswinds Trail, 5 sights, gaining 674 ft, and the network tops out at 233 ft.
- Wayont Road Loop 1.9 mi · ▲ 118 ft
- Gramp's Loop 2 mi · ▲ 85 ft
- Liggett Road 2.3 mi · ▲ 93 ft
- South Line Road Loop 2.4 mi · ▲ 0 ft
- Kamesit Road Loop 2.4 mi · ▲ 144 ft
- Briggs Road–Halfway Pond Road, 3 sights 2.5 mi · ▲ 55 ft
- Maple Springs Road 2.6 mi · ▲ 0 ft
- Dunham Road & East Beeme Road Loop via West Line Road 2.7 mi · ▲ 89 ft
- East Head Pond–New Long Pond, 3 lakes 2.9 mi · ▲ 54 ft
- Federal Pond Road Loop 2.9 mi · ▲ 176 ft
- Webster Springs Road 3 mi · ▲ 55 ft
- Bentley Loop 3 mi · ▲ 108 ft
- Little Long Pond & Southeast Line Road Loop 3.1 mi · ▲ 55 ft
- Gunners Exchange Pond & Crooked Pond Loop 3.1 mi · ▲ 202 ft
- Abner Pond & Sasemine Way 3.1 mi · ▲ 26 ft
- Frogfoot Brook Reservoir via Wompanoag Road 3.2 mi · ▲ 0 ft
- Priscilla Road 3.2 mi · ▲ 57 ft
- New Long Pond–Three Cornered Pond Loop, 3 lakes 3.2 mi · ▲ 57 ft
- East Beeme Road–Jessup Road, 3 sights 3.4 mi · ▲ 30 ft
- Jessup Road 3.4 mi · ▲ 138 ft
- Sabbatia Road Loop via Three Cornered Pond Road 3.4 mi · ▲ 26 ft
- Hog Rock Road 3.5 mi · ▲ 54 ft
- Three Cornered Pond–Kamesit Road Loop, 3 sights 3.5 mi · ▲ 167 ft
- Abner Pond–Grassy Pond Loop, 4 sights 3.7 mi · ▲ 27 ft
- Wompanoag Road Loop 3.7 mi · ▲ 54 ft
- Halfway Pond Road 3.8 mi · ▲ 114 ft
- Barrett Pond–Dunham Road Loop, 4 sights 4.1 mi · ▲ 136 ft
- Barrett Pond & Jessup Road 4.1 mi · ▲ 53 ft
- Crane Brook Bog Reservoir & Halfway Pond Road 4.2 mi · ▲ 80 ft
- Halfway Pond via East Line Road 4.2 mi · ▲ 193 ft
- Frogfoot Brook Reservoir via Wompanoag Road 4.4 mi · ▲ 59 ft
- Three Corners Pond Road Loop 4.5 mi · ▲ 199 ft
- Charge Pond Loop Trail & Charge Pond Loop Loop 4.7 mi · ▲ 27 ft
- Harlow Brook Reservoir via South Line Road 4.7 mi · ▲ 27 ft
- Little South Pond 4.8 mi · ▲ 259 ft
- New Grassy Pond–Grassy Pond, 3 lakes 5.1 mi · ▲ 0 ft
- Southeast Line Road 5.1 mi · ▲ 106 ft
- Howland Road 5.5 mi · ▲ 352 ft
- East Line Road Loop 5.9 mi · ▲ 202 ft
- Bentley Loop & Cobb Road 5.9 mi · ▲ 111 ft
- Long Pond & Halfway Pond via Three Corners Pond Road 6.4 mi · ▲ 302 ft
- Federal Pond–Rocky Pond, 3 lakes 6.4 mi · ▲ 190 ft
- Rocky Pond & Kamesit Road 6.7 mi · ▲ 225 ft
- Federal Hill–Federal Pond, 3 summits 6.8 mi · ▲ 172 ft
- Cobb Road via Agawam Road 7.8 mi · ▲ 215 ft
- Besse Bog Reservoir–Little Five Mile, 3 lakes 8.7 mi · ▲ 221 ft
- Great South Pond & Kamesit Road 9 mi · ▲ 224 ft
- Glen Charlie Pond–East Head Pond, 7 lakes 9.3 mi · ▲ 191 ft
- Tihonet Pond–East Head Pond, 4 lakes 9.4 mi · ▲ 85 ft
- Little Five Mile–Abner Pond, 3 lakes 9.6 mi · ▲ 272 ft
- White Island Pond–East Head Pond, 8 lakes 10.3 mi · ▲ 243 ft
- Grassy Pond–Abner Pond, 4 sights 10.6 mi · ▲ 163 ft
- Abner Pond & Priscilla Road via East Line Road 11 mi · ▲ 193 ft
- Crooked Pond–Dunham Road, 4 sights 11.4 mi · ▲ 454 ft
- Crosswinds Trail–Pilgrim Loop, 4 sights 11.5 mi · ▲ 504 ft
- East Head Bog Reservoir–Jessup Road, 4 sights 12.3 mi · ▲ 567 ft
- Maple Springs Brook Reservoir–Little Long Pond, 3 lakes 12.6 mi · ▲ 247 ft
- Russell Millpond–Crosswinds Trail, 5 sights 14.6 mi · ▲ 674 ft
- Crosswinds Trail–Dunham Road, 5 sights 16 mi · ▲ 516 ft