Best trails in Chesapeake

1007 Reviews
Looking for a great trail near Chesapeake, Virginia? AllTrails has 18 great hiking trails, running trails, mountain biking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around First Landing State Park or Merchants Millpond State Park, we've got you covered. You'll also find some great local park options, like Indian River Park or Oak Grove Lake Park. Just looking to take a quick stroll? We've got 18 easy trails in Chesapeake ranging from 0.6 to 16.5 miles and from 0 to 22 feet above sea level. Start checking them out and you'll be out on the trail in no time!
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Map of trails in Chesapeake
Top trails (18)
#1 - Indian River Park Trail
Indian River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(202)
Length: 2.1 mi
Indian River Park Trail is a 2.1 mile moderately trafficked loop trail located near Chesapeake, Virginia that features a river and is good for all skill levels. The trail is primarily used for nature Show more
#2 - Oak Grove Lake
Oak Grove Lake Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(205)
Length: 1.9 mi • Est. 46 m
Oak Grove Lake is a 1.9 mile heavily trafficked loop trail located near Chesapeake, Virginia that features beautiful wild flowers and is good for all skill levels. The trail offers a number of activitShow more
#3 - Molly Mitchell, Otter Point and Indian Creek Loop
Northwest River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(80)
Length: 4.2 mi • Est. 1 h 42 m
Molly Mitchell, Otter Point and Indian Creek Loop is a 4.2 mile moderately trafficked loop trail located near Chesapeake, Virginia that features a lake and is good for all skill levels. The trail offeShow more
#4 - Chesapeake Arboretum North and South Loop
Chesapeake Arboretum
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(129)
Length: 2 mi • Est. 49 m
NOTE: As of January 2020, the south loop bridge is closed. The Chesapeake Arboretum has more than two and a half miles of hiking trails for all abilities. For those with walking difficulties there aShow more
#5 - Dismal Swamp Canal Trail
Chesapeake, Virginia
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(78)
Length: 16.5 mi • Est. 6 h 40 m
The Dismal Swamp Canal Trail is a former section of Virginia State Rt. 17, now a multiuse trail open to bicycling, walking, running, horseback riding, and boating. The north trailhead is located at thShow more
#6 - Deer Island and Shuttle Trail Loop to Otter Point Overlook
Northwest River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(47)
Length: 2.6 mi • Est. 1 h 3 m
Beautiful View of Northwest River from Picnic Area where otters are sometimes observed. Northwest River Park has it all! There are over 7 miles of hiking trails including 2 miles of biking trails andShow more
#7 - Great Bridge Battlefield and Waterways Park Loop
Great Bridge Battlefield & Waterways Historic Kark
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(65)
Length: 1.2 mi • Est. 29 m
Great Bridge Battlefield and Waterways Park Loop is a 1.2 mile loop trail located near Chesapeake, Virginia that features a river. The trail is good for all skill levels and offers a number of activitShow more
#8 - Miller Avenue Biking and Walking Trail
Indian River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray StarGray Star(46)
Length: 3.4 mi • Est. 1 h 24 m
Heavily used by bikes. It has lots of jump courses set up. The back section off the end of Miller Avenue is the most heavily used. Nice wooded trails. You can do an outside loop of 2 miles but thereShow more
#9 - Indian Creek Trail
Northwest River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(26)
Length: 3.8 mi • Est. 1 h 32 m
A nice walk in the woods but not as much to see as some of the trails in the park. Located inside Northwest River Park.Show more
#10 - Molly Mitchell Trail
Northwest River Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(29)
Length: 2.7 mi • Est. 1 h 5 m
Molly Mitchell Trail is a 2.7 mile lightly trafficked out and back trail located near Chesapeake, Virginia that features a river and is good for all skill levels. The trail is primarily used for hikinShow more
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