Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Login or Signup

Routes
Hikes

Chesapeake

Routes
Hikes

Chesapeake

The best family-friendly hikes and walks in Chesapeake city

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.

Best family friendly hiking trails in Chesapeake city

  • The most popular family friendly hiking route is Dismal Swamp Canal Trail

Last updated: April 25, 2026

#1.

Dismal Swamp Canal Trail

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.

Navigate with device

Send to Phone

Save

Moderate

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…

Easy
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

5.0

(7)

58

hikers

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.

Easy

4

hikers

Hike the easy 2.6-mile Elisabeth River trail loop in Norfolk, Virginia, enjoying waterfront views and historic landmarks like the Battleship

Easy

5.0

(4)

3

hikers

Hike the easy 1.7-mile (2.7 km) Chesapeake Arboretum North Loop through a dense hardwood forest with views of Lake Hughes.

Easy
Sign up for free to see 30 more hikes in Chesapeake city.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Chesapeake

Family-friendly hikes around Chesapeake

Family-friendly hikes in Great Dismal Swamp National Wildlife Refuge

Tips from the Community

Isamoor92
January 4, 2026, Oak Grove Lake Park

Beautiful path, accessible to everyone

Translated by Google

0

0

Very interesting ship

Translated by Google

0

0

There are a couple of these mermaids

Translated by Google

0

0

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!

Translated by Google

0

0

Alex
May 15, 2025, Chessie the Bear

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

0

0

Beautiful path along the river. Many events take place here in the summer.

Translated by Google

0

0

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.

1

0

It's incredibly impressive what people have always been capable of.

Translated by Google

2

1

Frequently Asked Questions

How many family-friendly hiking trails are available in Chesapeake?

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.

What is the best time of year for family hikes in Chesapeake?

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.

Are there any stroller-friendly trails suitable for families with very young children?

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.

What kind of natural features can we expect to see on family hikes in Chesapeake?

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.

Are there any circular routes that are good for families?

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.

What do other hikers enjoy the most about family-friendly hiking in Chesapeake?

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.

Are dogs allowed on family hiking trails in Chesapeake?

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.

Are there any specific landmarks or points of interest along these family-friendly routes?

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.

Are there any easy trails that offer a good chance to see wildlife?

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.

Where can we find parking for these family-friendly trails?

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.

Are there any family-friendly trails near water?

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.

Most popular routes in Chesapeake city

Hiking in Chesapeake city

Most popular attractions in Chesapeake city

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Didn’t find what you were looking for?

Check out more Hikes throughout Chesapeake below and find the perfect route in your destination.

Great Dismal Swamp National Wildlife RefugeChesapeake

Nearby adventure guides

Things to Do around Chesapeake

Natural areas to explore nearby

Things to Do in Plum Tree Island National Wildlife Refuge

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy