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Chessie the Bear – Dismal Swamp Trail loop from Cavalier

Chessie the Bear – Dismal Swamp Trail loop from Cavalier

Moderate

3.3

(8)

riders

Chessie the Bear – Dismal Swamp Trail loop from Cavalier

02:10

47.0km

20m

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: June 15, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 240 m for 3.40 km

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

After 43.4 km for 3.40 km

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

Waypoints

Start point

Parking

Get Directions

27 m

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

305 m

Chessie the Bear

Highlight • Monument

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

Tip by

44.7 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

47.0 km

End point

Parking

Way Types & Surfaces

Way Types

20.7 km

18.1 km

7.80 km

524 m

Surfaces

27.8 km

18.8 km

524 m

Elevation

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

Weather

Tuesday 30 June

31°C

18°C

-- %

Additional weather tips

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Comments

August 24, 2024,Group Ride with the Swamp Pedalers

My buddy Kevin and I joined a local cycling group, the Swamp Pedalers, for a mostly casual ride around the Dismal Swamp trail. For the last 10 miles or so, i joined some of the faster riders and we did 18-20 mph with some brief sprints at 26 mph. It was a great ride.