4.8
(39)
352
hikers
34
hikes
Family friendly hiking trails in Chesapeake City traverse a diverse landscape characterized by extensive forests, wetlands, and numerous waterways, including the Elizabeth River and Lake Drummond. The region offers a mix of natural parks and protected areas, providing varied ecosystems for exploration. Hikers can experience waterfront views, mature hardwoods, and unique wetland environments, making it suitable for outdoor activities year-round.
Last updated: April 25, 2026
13.1km
03:17
0m
0m
Hike the 8.2-mile Dismal Swamp Canal Trail, a flat, historic route through the Great Dismal Swamp National Wildlife Refuge.
7.27km
01:49
0m
0m
Embark on an easy hike along the Washington Ditch Trail, a flat and well-maintained path stretching 4.5 miles (7.3 km) through the serene Great Dismal Swamp. You will experience a…

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5.0
(7)
58
hikers
2.96km
00:44
0m
0m
Hike the easy 1.8-mile Oak Grove Lake Park Trail, a flat loop around Oak Grove Lake with scenic views and wildlife spotting opportunities.
4
hikers
4.13km
01:02
0m
0m
Hike the easy 2.6-mile Elisabeth River trail loop in Norfolk, Virginia, enjoying waterfront views and historic landmarks like the Battleship
5.0
(4)
3
hikers
2.66km
00:40
0m
0m
Hike the easy 1.7-mile (2.7 km) Chesapeake Arboretum North Loop through a dense hardwood forest with views of Lake Hughes.
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Beautiful path, accessible to everyone
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Very interesting ship
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There are a couple of these mermaids
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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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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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Nice place to jog as there are trees along most of the trail to provide shade and a wind barrier. The trail itself is mostly packed dirt or gravel and a loop is 1.5 miles around making it a nice place to train for the 5K, 10K and Half Marathon distances.
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It's incredibly impressive what people have always been capable of.
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Chesapeake offers a wide selection of family-friendly hiking options, with over 30 easy trails perfect for all ages. In total, you'll find around 35 routes suitable for various skill levels, ensuring there's always a new adventure waiting.
Chesapeake's temperate weather makes it suitable for hiking year-round. Spring brings blooming flora, while autumn offers beautiful foliage. Even in winter, the trails are often accessible and provide a peaceful experience. Summer can be warm, so early mornings or late afternoons are best.
Yes, several trails in Chesapeake are well-suited for strollers. The Oak Grove Lake Park Trail, for example, is an easy, paved loop around the lake, perfect for strollers and young walkers. The Dismal Swamp Canal Trail also offers a long, flat, and generally smooth surface ideal for strollers.
Chesapeake's trails showcase diverse natural beauty, from vast forests and wetlands to scenic waterfronts. You can expect to see mature hardwoods, pine forests, and marsh overlooks. Many trails offer views of lakes like Lake Hughes and Oak Grove Lake Park, as well as access to rivers and canals. Keep an eye out for diverse wildlife, especially birds and butterflies.
Absolutely! Circular routes are great for families as they bring you back to your starting point. The Oak Grove Lake Park Trail is an easy 1.8-mile loop around a lake, offering scenic views and wildlife spotting. Another option is the Chesapeake Arboretum North Loop, which takes you through beautiful themed gardens and wooded areas.
The komoot community highly rates the family-friendly trails in Chesapeake, with an average score of 4.8 stars. Reviewers often praise the well-maintained paths, the peaceful natural settings, and the accessibility for all ages. Many appreciate the opportunity to observe local wildlife and enjoy scenic lake or river views.
Many parks and trails in Chesapeake are dog-friendly, but leash rules are generally enforced to ensure the safety and enjoyment of all visitors and wildlife. It's always a good idea to check specific park regulations before you go, but trails like the Dismal Swamp Canal Trail are popular choices for walks with your leashed canine companions.
Yes, several trails feature interesting landmarks. For instance, the Chesapeake Arboretum North Loop guides you through themed gardens and past Lake Hughes. The Dismal Swamp area, including the Dismal Swamp Trail, is a significant natural landmark known for its unique ecosystem and wildlife. You can also visit Northwest River Park for its extensive trail system and waterfront access.
Absolutely! The Oak Grove Lake Park Trail is an excellent choice for wildlife viewing, with opportunities to spot various birds and aquatic life around the lake. The trails within the Great Dismal Swamp National Wildlife Refuge, such as the Washington Ditch Trail, are also prime locations to observe diverse flora and fauna, including many bird species.
Most major parks and trailheads in Chesapeake offer dedicated parking facilities. For example, Oak Grove Lake Park and the Chesapeake Arboretum have ample parking. For trails like the Dismal Swamp Canal Trail, there are designated parking areas at various access points along its length.
Many of Chesapeake's family-friendly trails offer beautiful water views. The Oak Grove Lake Park Trail loops directly around a serene lake. The Elisabeth River trail loop provides scenic access to the river, and the Dismal Swamp Canal Trail runs alongside the historic Intracoastal Waterway, offering unique canal views.


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