Dismal Swamp Trail – Chessie the Bear loop from Grassfield High School

Dismal Swamp Trail – Chessie the Bear loop from Grassfield High School

Moderate

3.0

(23)

riders

Dismal Swamp Trail – Chessie the Bear loop from Grassfield High School

02:54

66.1km

50m

Road cycling

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: October 8, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 56.8 km for 3.40 km

Open: • Public holidays & Monday-Sunday: sunrise-sunset (otherwise closed)

After 60.5 km for 130 m

Open: • Public holidays & Monday-Sunday: sunrise-sunset (otherwise closed)

Waypoints

Start point

Parking

Get Directions

6.94 km

Southern Branch Elizabeth River

Lake

58.2 km

Dismal Swamp Trail

Highlight (Segment) • Trail

Paved bicycle and walking trail along the canal. Plenty of facilities along the way, such as bathrooms and bicycle repair stands. Awesome colors on the trees in the fall.

Tip by

60.6 km

Chessie the Bear

Highlight • Monument

Chessie the Bear, an endearing wooden sculpture of a bear, and a photo opportunity!

Tip by

60.9 km

Bicycle Repair Station at Mile Post 4

Highlight • Rest Area

Rest stop at Mile Post 4'. Parking area and public restrooms. You will also find a bicycle repair station here where you can hang your bike up, have access to some tools and a pump.

Tip by

66.1 km

End point

Parking

Way Types & Surfaces

Way Types