Trout Brook Valley
Lots of really technical single track and a few fire roads. Closed during the Winter. Some trails are off limits to bikes. mtbr.com
Trumbull Rail Trail
First section of the rail trail, 3 miles, is unpaved. Next 3 miles is paved and there are plans to continue the trail to the Monroe Town line but there is a missing bridge which is barring the way at the moment. Good pl... singletracks.com
Indian Ledge Trail
The amphitheater in Indian Ledge Park has most recently hosted acts like The Beach Boys, Clearwater Revisited, Hall and Oates, KC and the Sunshine Band, REO Speedwagon and Train... patch.com
Roosevelt Forest
For a four-season nature experience, Roosevelt Forest in north Stratford, on the Shelton border, is a great destination for residents... patch.com
Housatonic Rail - Trail –...
Monroe residents use this largely forested 4.3- mile section of the Housatonic (known locally as the Monroe Railbed Trail) as a convenient bike route to William E. Wolfe Park. Visiting rail-trail users also gravitate around t... trails.com
Housatonic Rail - Trail –...
A shady respite from suburban Trumbull, this fairly flat trail overlooks the winding Pequonnock River for much of its 3.4 miles. Rapids and distinctive rock outcrops add interest. The trail begins on the railroad corridor, st... trails.com
Trumbull Old Mine Park
Just north of the town of Trumbull, off Connecticut Highway 25. The terrain is flat, except for a short, steep climb on a loose gravel jeep road and a steep descent on pavement leaving the park. Be ready to change riding tech... trails.com
Monroe Rail Trail
Rail Trail. Some Single Track branching off but nothing but little outtakes. Fun for family riding. singletracks.com
Derby Greenway
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes across O'Sullivan's Islan... traillink.com
Housatonic Rail-trail In Trumbull (Pequonnock Valley Greenway)
The Housatonic Rail-Trial in Trumble, a.k.a., the Pequonnock Valley Greenway, offers a shady respite from suburban Trumbull, this fairly flat trail overlooks the winding Pequonnock River for much of its 3.4 miles. Rapids a... traillink.com
Housatonic Valley Rail-trail In Monroe
The Housatonic Rail-Trail in Monroe is a northern continuation of the Trumbull segment of the rail-trail. Locals refer to it as the Monroe Housatonic Railbed Trail. The 4.3-mile trail is largely forested and is a convenien... traillink.com