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Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

Easy

4.7

(6231)

12,441

riders

Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

01:45

42.8km

30m

Road cycling

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: April 15, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 12.4 km for 130 m

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

After 12.8 km for 3.40 km

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

Waypoints

Start point

Parking

Get Directions

12.1 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

12.4 km

Chessie the Bear

Highlight • Monument

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

Tip by

12.6 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

26.0 km

Chesapeake Regional Airport

Highlight • Rest Area

Small regional airport. Both public and private. Serving the Chesapeake and Norfolk areas. Owned by the Chesapeake Airport Authority and used by light aircraft and smaller jets.

Tip by

42.8 km

End point

Parking

Way Types & Surfaces

Way Types

29.8 km

6.22 km

5.89 km

913 m

Surfaces

35.6 km

6.92 km

260 m

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Weather

Today

Wednesday 20 May

34°C

21°C

0 %

Additional weather tips

Max wind speed: 17.0 km/h

to get more detailed weather forecasts along your route

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

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Chessie the Bear – Dismal Swamp Trail loop from Dollar Tree

Bicycle Repair Station at Mile Post 4

Chessie the Bear

Dismal Swamp Trail

Chesapeake Regional Airport

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