Best hikes in Rockland Preserve
Ambleway maps 27 hikes in Rockland Preserve, from a 1.9-mile walk to a 12-mile day out. All of them score as wild, staying clear of roads and development for most of the route; the wildest is Crooked Hill Road. The biggest climb is Coginchaug Cave–Bridle Loop, 8 sights, gaining 1,280 ft, and the network tops out at 687 ft.
- Boundary Trail & Lone Pine Trail 1.9 mi · ▲ 295 ft
- Crooked Hill Road 2 mi · ▲ 116 ft
- Beyond Thunderdome–Eastern Loop Loop, 6 sights 2.2 mi · ▲ 344 ft
- Stannard Pond–Rishy, 3 sights 2.4 mi · ▲ 218 ft
- Stannard Pond–Whitney Pond, 4 sights 2.9 mi · ▲ 286 ft
- Old Crooked Hill Road & Whitney Road via Eratica 3 mi · ▲ 234 ft
- Glacial Erratic–Dave Houston Trail, 3 sights 3.2 mi · ▲ 261 ft
- Mount Pisgah–Glacial Erratic, 6 sights 3.2 mi · ▲ 416 ft
- Whitney Pond–Coan Pond Loop, 5 sights 3.3 mi · ▲ 142 ft
- Pyramid Rock–Glacial Erratic, 5 rocks 3.3 mi · ▲ 144 ft
- New England Viewpoint–Coan Pond Loop, 4 sights 3.5 mi · ▲ 269 ft
- New England Viewpoint–Stannard Pond, 3 sights 3.7 mi · ▲ 394 ft
- Vista–Boundary Trail, 7 sights 3.8 mi · ▲ 628 ft
- New England Viewpoint–Coan Pond Loop, 4 sights 4.1 mi · ▲ 429 ft
- Selectmen's Stones–New England Viewpoint, 7 sights 4.3 mi · ▲ 475 ft
- Meyerhuber Pond–Bridle Loop, 4 sights 4.6 mi · ▲ 575 ft
- Lone Pine Trail & Whitney Road via New England Trail 4.6 mi · ▲ 667 ft
- Broomstick Ledges–New England Trail, 3 sights 5.8 mi · ▲ 589 ft
- Coan Pond Viewpoint–Dirt Church, 6 sights 6.1 mi · ▲ 718 ft
- Spot Pond & Whitney Road via New England Trail 6.6 mi · ▲ 606 ft
- Dodge Dump Truck–Bridle Loop, 3 sights 7 mi · ▲ 819 ft
- New England Viewpoint–Meyerhuber Pond, 9 sights 7.7 mi · ▲ 1,103 ft
- Coginchaug Cave–Bridle Loop, 8 sights 8.8 mi · ▲ 1,280 ft
- Stair Brook Falls–Meyerhuber Pond, 5 sights 9.8 mi · ▲ 1,260 ft
- Bridle Loop–Goat Hill Road, 5 sights 10.4 mi · ▲ 936 ft
- Guilford Sportsmens Club Pond–New England Trail, 3 sights 12.3 mi · ▲ 959 ft
- Quonnipaug Lake–Glacial Erratic, 8 sights 12.4 mi · ▲ 1,250 ft