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Chesapeake, Virginia

Looking for the best hiking in Chesapeake? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Chesapeake. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Chesapeake

  • Williamsburg, Virginia

    Bike Jamestown Island

    5.1 mi / 45 ft gain
    The trail is open to cyclists and pedestrians, but does share the road with some vehicle traffic. The speed limit is slow and often there is little traffic. There also is no parking at the actual trail head, so one must begin at the Visitor Center Parking lot. The trail will show off the natural ...
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  • Williamsburg, Virginia

    Waller Mill Reservoir & Tower Trail

    4.0
    2.64 mi / 213 ft gain
    Waller Mill Reservoir & Tower Trail is a loop trail that takes you by a lake located near Williamsburg, Virginia.
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  • Williamsburg, Virginia

    Hike the Riverview Trail

    4.0
    7.5 mi / 150 ft gain
    From the parking area at the visitor center, pick up the Backbone Trail marked with gold blazes.  The trails are well marked with signage and arrows.  Follow the Backbone Trail for 2 miles under you reach the trail junction of Powhatan Forks Trail.  After a half mile the this trail splits with th...
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