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Routes
Road cycling routes
United States
Virginia
Chesapeake

Chesapeake

The best traffic-free bike rides around Chesapeake

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.

Best no traffic road cycling routes around Chesapeake

  • The most popular no traffic…

Last updated: April 27, 2026

20

riders

#1.

Chesapeake Regional Airport – Chessie the Bear loop from Walgreens

57.2km

02:32

30m

30m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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Moderate

19

riders

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy
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Tips from the Community

Alex
May 15, 2025, Chessie the Bear

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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Frequently Asked Questions

How many no-traffic road cycling routes are available in Chesapeake?

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.

What is the terrain like on Chesapeake's no-traffic road cycling routes?

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.

Are there any family-friendly no-traffic cycling routes in Chesapeake?

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.

What kind of wildlife can I expect to see on these routes?

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.

Are there any circular no-traffic road cycling routes?

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.

What are some notable landmarks or attractions along the no-traffic cycling routes?

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.

What is the best time of year to cycle these routes?

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.

Are there facilities like restrooms or picnic areas along the trails?

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.

Is parking available at the trailheads for these routes?

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.

What do other cyclists say about road cycling in Chesapeake?

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.

Are there any unique cycling experiences in Chesapeake with some elevation?

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.

Can I rent bikes in Chesapeake?

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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