4.8
(11)
473
riders
55
rides
Road cycling routes in Chesapeake city are characterized by generally flat terrain and an extensive network of multi-use trails. The region features diverse landscapes, including tranquil forests, expansive wetlands, and scenic riverfronts. These conditions provide an ideal setting for road cyclists seeking varied experiences across well-maintained paths.
Last updated: May 5, 2026
5.0
(1)
7
riders
19.0km
00:51
20m
20m
Cycle the easy 11.8-mile Elizabeth River Trail in Norfolk, enjoying waterfront views, historic sites, and the unique "Glowline".
3.0
(1)
3
riders
100km
04:03
90m
90m
This moderate 62.2-mile (100.1 km) road cycling loop connects Norfolk and Virginia Beach, offering diverse urban, coastal, and park scenery.

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38.0km
01:29
30m
30m
This easy 23.6-mile road cycling loop from Portsmouth to Churchland, Virginia, offers flat terrain and takes about 1 hour and 29 minutes.
20
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
20
riders
20.2km
00:58
10m
10m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
17
riders
42.7km
01:47
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
18
riders
58.0km
02:29
30m
30m
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.
4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
6
riders
50.1km
02:05
60m
60m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Very interesting ship
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A very impressive battleship from World War II, which, after several decommissionings and recommissions, remained in service until the 1990s, where it was regularly modernized. It was only finally struck from the Naval Vessel Register in 2006 and donated to the city of Norfolk as a museum ship. You can tour many areas of the ship, including the upper deck and the interior. Despite the relatively high admission price, a visit to the ship is definitely worthwhile for anyone interested in technology and naval history. If you'd like to see a few more sights, you should purchase the Passport for Fun for just over $50. This allows you to visit the ship, the Oceanographic Museum, the Botanical Garden, and the Norfolk Zoo, in addition to the ship. A little tip: Navy personnel in uniform are admitted free!
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Pop into Equinox Coffee—rumored to be the spot for cyclists on 2800 Colley Ave in Norfolk—to refuel during or after your ride. They serve quality espresso and lattes in a cozy, friendly space with bike racks outside and clean restrooms inside.
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Town Point Park serves as a vibrant hub on the Elizabeth River Trail in downtown Norfolk. Start or pause your ride here—enjoy waterfront views, public art, and access to the park’s amenities. You’ll find bike racks, nearby restrooms, and seasonal fountains. From here, you can reconnect with the 10.5-mile riverside trail that leads to Nauticus, the USS Wisconsin, and charming neighborhoods. It’s the perfect urban cycling spot to combine city sights with easy trail riding.
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Chessie the Bear, an endearing wooden sculpture of a bear, and a photo opportunity!
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Beautiful path along the river. Many events take place here in the summer.
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The park is open sunrise to sunset. Many tree lined, shaded miles of hiking, cycling and horse trails throughout the park. Great fishing spots and campground too.
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Chesapeake offers a wide variety of road cycling routes, with over 50 routes available on komoot. These routes cater to different preferences, including 34 easy, 18 moderate, and 1 difficult option.
The most popular months for road cycling in Chesapeake are May and June, thanks to the temperate weather conditions. However, the generally mild climate makes it suitable for cycling throughout much of the year.
Chesapeake is known for its generally flat terrain, making it very suitable for road cycling. Routes often feature well-paved surfaces and extensive multi-use trails, winding through diverse landscapes from tranquil forests and wetlands to scenic riverfronts.
Yes, many of Chesapeake's road cycling routes are suitable for families due to the flat terrain and well-maintained multi-use trails. The Elizabeth River Trail, for example, is an easy 11.8-mile route offering waterfront views and urban scenery, perfect for a family outing.
Road cycling in Chesapeake offers views of diverse natural features and landmarks. You can explore the expansive Great Dismal Swamp National Wildlife Refuge, cycle around Oak Grove Lake Park, or enjoy the trails at Northwest River Park. The Dismal Swamp Trail is particularly popular for wildlife observation.
Absolutely. For those seeking a longer challenge, the Norfolk to Virginia Beach metric century loop is a moderate 62.2-mile route offering varied urban and coastal landscapes. Another option is the Northwest River Park – The Blackwater Trading Post loop from Ingleside Road, which spans over 70 miles.
Yes, many road cycling routes in Chesapeake are designed as loops, providing a convenient way to start and end your ride at the same point. Examples include the Chessie the Bear – Dismal Swamp Trail loop from Ballahack Boat Ramp and the Chessie the Bear loop from Cornland Park.
The road cycling routes in Chesapeake are highly rated by the komoot community, with an average score of 4.6 stars. Reviewers often praise the region's generally flat and well-maintained multi-use trails, as well as the diverse scenery ranging from tranquil forests to scenic riverfronts.
For unique urban and waterway vistas, consider cycling the walking path on the South Norfolk Jordan Bridge. It offers a 5% incline and panoramic views from 169 feet above the water. The Elizabeth River Trail also provides excellent waterfront and urban scenery.
Chesapeake is very beginner-friendly for road cyclists, with 34 easy routes available. The Elizabeth River Trail is an excellent choice, offering a relatively short distance and minimal elevation gain. Another easy option is the Portsmouth to Churchland, Virginia loop.
When cycling through areas like the Great Dismal Swamp National Wildlife Refuge, you might spot a variety of wildlife. This refuge is home to over 200 species of birds, nearly 100 species of butterflies, and mammals such as flying squirrels, red foxes, and even black bears. Oak Grove Lake Park is also known for butterflies, dragonflies, and songbirds.
Yes, several routes allow you to experience the Great Dismal Swamp. The Chessie the Bear – Dismal Swamp Trail loop from Ballahack Boat Ramp is a popular 11.9-mile route that takes you directly through this unique natural area, offering opportunities for wildlife observation.


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