Great Rides Boston - Trek Bikes

Wondering where to ride? We got you. Check out our curated collection of local road, family, and mountain bike routes. Here, you’ll find the best places to bike in Boston along with great cycling routes in Cambridge, Medford, Somerville, Watertown, and many more. Browse these options for guidance on where to ride in Boston, GPS files, and metrics on your ride, like distance and elevation.

Here are a few of our favorite Boston rides.

Beaver Brook North

Distance: 9 mi
248 Mill St, Belmont, MA 02478

Blue Hills Reservation

Distance: 105 mi
Houghton's Pond Recreation Hillside St, Milton, MA 02186

Cutler Park

Distance: 17 mi
Cutler Park Reservation, 84 Kendrick St, Needham, MA 02494

Great Brook Farm State Park

Distance: 22 mi
984 Lowell Street Carlisle Massachusetts 01741

Harold Parker State Forest

Distance: 55 mi
90-106 Harold Parker Rd, Andover, MA 01810

Landlocked Forest

Distance: 13 mi
Burlington Landlocked Forest, Lexington, MA 02420

Lynn Woods

Distance: 28 mi
118 Great Woods Rd, Lynn, MA 01904

Middlesex Fells Reservation

Distance: 61 mi
Lower Sheep Fold Parking Lot, Stoneham, MA 02180

Andala River

Distance: 30.3 mi
Elevation: +/- 665 ft
Cambridge, MA

Black Sheep Bomb!

Distance: 108.7 mi
Elevation: +/- 4955 ft
Cambridge, MA

Great Meadows

Distance: 37.3 mi
Elevation: +/- 1974 ft
Watertown, MA

Lexington

Distance: 28 mi
Elevation: +/- 1274 ft
Cambridge, MA

Lexington Long

Distance: 45.3 mi
Elevation: +/- 2040 ft
Cambridge, MA

Maynard Madness

Distance: 52 mi
Elevation: +/- 2227 ft
Watertown, MA

Sarah's Ride Long

Distance: 40.9 mi
Elevation: +/- 1565 ft
Cambridge, MA

Tamper 27

Distance: 27.2 mi
Elevation: +/- 1387 ft
Medford, MA

Fresh Pond

Distance: 3 mi
Elevation: +/- 46 ft
Cambridge, MA

Boston Common Ride - Long

Distance: 2.1 mi
Elevation: +/- 72 ft
Boston, MA

Charles River

Distance: 2.1 mi
Elevation: +/- 72 ft
Boston, MA

Charles River - Long

Distance: 6.2 mi
Elevation: +/- 86 ft
Boston, MA

Constitution Wharf

Distance: 10.8 mi
Elevation: +/- 179 ft
Boston, MA

Franklin Park

Distance: 6.8 mi
Elevation: +/- 102 ft
Boston, MA

Reservoir Ride Long

Distance: 3.1 mi
Elevation: +/- 47 ft
Stoneham, MA

Mystic Lakes

Distance: 6.1 mi
Elevation: +/- 165 ft
Medford, MA

Boxborough

Distance: 8.7 mi
Elevation: +/- 663 ft
Boxborough, MA

North Bridge

Distance: 15.8 mi
Elevation: +/- 447 ft
Concord, MA

Saxonville

Distance: 17.5 mi
Elevation: +/- 665 ft
Framingham, MA

Trunkline

Distance: 47.8 mi
Elevation: +/- 1503 ft
Franklin, MA

Holliston Epic

Distance: 34.4 mi
Elevation: +/- 1597 ft
Holliston, MA

Sudbury

Distance: 16.9 mi
Elevation: +/- 509 ft
Newton, MA

Rutland

Distance: 42.2 mi
Elevation: +/- 3186 ft
Rutland, MA

Cutler Park

Distance: 10.7 mi
Elevation: +/- 273 ft
Needham, MA