4.8
(11)
473
riders
10
rides
Road cycling around Chesapeake offers a diverse landscape characterized by generally flat terrain and an extensive network of multi-use trails. The region features riverine paths and routes that traverse areas near swamps and open landscapes, providing a consistent riding experience with minimal elevation changes. This environment is ideal for no traffic road cycling routes, allowing cyclists to explore natural features such as forested wetlands and scenic waterways.
Last updated: April 27, 2026
20
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
19
riders
20.2km
00:58
10m
10m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

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5.0
(1)
13
riders
68.2km
03:00
40m
40m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
4
riders
42.8km
01:45
30m
30m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Chessie the Bear, an endearing wooden sculpture of a bear, and a photo opportunity!
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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.
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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.
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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.
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There are 9 dedicated no-traffic road cycling routes around Chesapeake featured in this guide. Most of these, 7 to be exact, are rated as easy, making them accessible for a wide range of cyclists.
Chesapeake is known for its generally flat terrain, making it ideal for road cycling. Routes often follow riverine paths and areas near swamps or open landscapes, providing a consistent riding experience with minimal elevation changes. The Dismal Swamp Trail – Chessie the Bear loop from Navy Exchange, for example, offers a very flat ride through forested wetlands.
Yes, many of Chesapeake's no-traffic routes are suitable for families due to their flat terrain and dedicated paths. The Chessie the Bear loop is an easy 20 km ride that's great for a family outing, offering a pleasant experience without significant challenges.
The routes, especially those near the Great Dismal Swamp National Wildlife Refuge like the Dismal Swamp Canal Trail, are excellent for wildlife viewing. You might spot diverse wildlife, including over 200 bird species and nearly 100 kinds of butterflies. Oak Grove Lake Park also offers opportunities to spot birds and other wildlife around its lake.
Yes, several routes are designed as loops, offering a convenient return to your starting point. The Chesapeake Regional Airport – Chessie the Bear loop from Walgreens is a moderate 57 km circular route, and the Chessie the Bear – Dismal Swamp Trail loop from Admiral Trailer Park is an easy 42 km option.
While cycling, you can encounter various points of interest. The Dismal Swamp Canal Trail features the famous 12-foot carved bear statue named "Chessie." You can also explore areas near Oak Grove Lake Park or the Elizabeth River Trail, which passes through parks and offers waterfront views. For more general attractions in the area, consider visiting the Battleship Wisconsin or the MacArthur Memorial.
Chesapeake's temperate weather allows for year-round cycling. However, spring and fall generally offer the most comfortable temperatures and beautiful scenery. Summer can be warm and humid, especially in the swamp areas, while winter is mild but can have cooler days. Be aware that mosquito activity can be higher in warmer, more humid months, particularly near wetlands.
Yes, some key trails are well-equipped. The Dismal Swamp Canal Trail, for instance, provides a bike repair/maintenance station, restrooms, and picnic areas, enhancing the cycling experience. Northwest River Park and Oak Grove Lake Park also offer amenities for visitors.
Parking is generally available at various access points for Chesapeake's trails. For example, parking is available at Elizabeth River Park for accessing the South Norfolk Jordan Bridge, and many parks like Northwest River Park and Oak Grove Lake Park offer dedicated parking facilities for visitors.
The no-traffic road cycling routes in Chesapeake are highly rated by the komoot community, with an average score of 4.7 stars. Reviewers often praise the region's flat, well-maintained paths, the serene natural beauty of areas like the Dismal Swamp, and the overall peaceful experience of cycling away from vehicle traffic.
While Chesapeake is generally flat, the South Norfolk Jordan Bridge offers a unique cycling experience with a 5% incline, raising riders 167-169 feet above the water. A round trip across this bridge provides panoramic views and a bit of a climb, connecting Chesapeake to Portsmouth.
Yes, Northwest River Park offers bike rentals, which can be a convenient option if you don't have your own bike or are visiting the area and want to explore its trails.


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