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

  • Chesapeake, Virginia

    Hike Indian River Park

    5.0
    2 mi / 0 ft gain
    When you're short on time and you need your daily dose of nature, Indian River Park is a quick little 'getaway'. It is best to park at Rokeby Center.  When you arrive to the park you'd be surprised that this little patch of nature exists in the middle of the town. The trail can be hard to follow ...
    Read more
  • Norfolk, Virginia

    Norfolk Botanical Gardens

    3.0
    3.74 mi / 308 ft gain
    Norfolk Botanical Gardens is a loop trail that takes you by a lake located near Norfolk, Virginia.
    Read more
  • Virginia Beach, Virginia

    Lake Lawson Loop Trail

    3.0
    1.5 mi / 305 ft gain
    Lake Lawson Loop Trail is a loop trail where you may see local wildlife located near Virginia Beach, Virginia.
    Read more
  • Virginia Beach, Virginia

    Cape Henry Trail

    10.06 mi / 72 ft gain
    Cape Henry Trail is an out-and-back trail that takes you by a lake located near Virginia Beach, Virginia.
    Read more
  • Virginia Beach, Virginia

    Hike the Bald Cypress Trail

    4.0
    1.8 mi
    This is an easy hike that meanders a bit more than any of the other trails in the park. It is also the most diverse in what you will see. The trail itself ranges from an easy foot path with a pine needle bed trail then passes through swamps and bog's via well crafted wood boardwalks with great vi...
    Read more
  • Virginia Beach, Virginia

    Hike the Osmanthus Trail

    4.5
    3 mi / 150 ft gain
    This loop hike is accessed from a short walk from the Bold Cypress Trail and the visitor center.  There are no views along this trail but the what I enjoyed was the pine needle covered trail itself.  The pine needles are like a soft carpet padding the trail.  I enjoy trailing running this loop mo...
    Read more
  • Virginia Beach, Virginia

    Bald Cypress Trail

    4.0
    1.72 mi / 26 ft gain
    Bald Cypress Trail is an out-and-back trail where you may see beautiful wildflowers located near Virginia Beach, Virginia.
    Read more
  • 64th Street, Virginia

    Hike the Osprey Trail at First Landing State Park

    4.3
    3.4 mi
    Get to First Landing State Park early. Whether it's a weekday in the summer or a Saturday in the winter, the park will be full of families, bikers, trail runners, dog walkers, and all manner of city folk (from DC, Baltimore, and Richmond) trying to meet their outdoor quota during a vacation or se...
    Read more
  • Virginia Beach, Virginia

    Hike the First Landing South Loop

    4 mi / 0 ft gain
    This loop starts from the First Landing State Park 64th Street Entrance parking lot. There is a $7 entrance fee to the State Park (it increases to $10 between April - October on the weekends), which can be paid when you arrive. When looking at the trail map I wanted to find a loop that would cove...
    Read more
  • Chesapeake, Virginia

    Hike the Northwest River Park East Loop

    3 mi / 0 ft gain
    When arriving at the park drive to Parking Lot 4 to park, this will give you the closest access to the trail head. Start heading Southeast along the Molly Mitchell Trail and continue on it until you reach the Shuttle Trail and take a left. You will only remain on this trail for a very short segme...
    Read more
  • Newport News, Virginia

    Hike Noland Loop Trail

    4.8
    4.8 mi / 154 ft gain
    Great hike right in the city of Newport News.  It is a loop trail that is 4.8 miles and has a moderate level of traffic.   Easy, good for all skill levels Pet friendly Water and wooded views with lots of shade throughoutClearly marked trail No bikesParking at Mariners Museum and at Lions Bridge; ...
    Read more
  • Virginia Beach, Virginia

    Catch A Sunset at the Munden Point Park Pier

    4.0
    0.1 mi / 0 ft gain
    Once in the park, you want to make your way to the most northern section of the park for the best sunset shots. Park in front of (south) of the softball field and follow the paved bike path right in front of you. The path heads north toward the water. Walk the 200 yard long path to the pier for e...
    Read more
  • Virginia Beach, Virginia

    Bike into False Cape State Park

    4.7
    Located in South Eastern Virginia Beach VA, False Cape State Park is only accessible by bike, foot, or tour. To get here, you must head in to Sandbridge Beach and drive south on Sandpiper Road until you pass the Little Island Pier parking on your left. After this point, there will be no more buil...
    Read more
  • Virginia Beach, Virginia

    Bike Camp False Cape

    It's hard to beat an outdoor adventure that keeps you near the ocean's edge. For this destination, getting there is possibly the best part. The trail is well kept and level; perfect for an easy bike ride or hike. An easy trail due to lack of incline (after all, it is by the sea). For the first fe...
    Read more
  • Virginia Beach, Virginia

    Catch Sunset on the Wild Shores of Back Bay National Wildlife Refuge

    5.0
    At the far south end of Virginia Beach’s Sandbridge community lies a seldom visited natural treasure, Back Bay National Wildlife Refuge.  The expansive beaches feel wilder than the shores just a few miles north and are littered with the footprints of sandpipers, rather than that of humans.  On th...
    Read more
  • Yorktown, Virginia

    Hike through Historic Yorktown

    5.0
    2.5 mi / 59 ft gain
    This is a fantastic hike through the history of the early United States. And one with many interactive exhibits and recreation opportunities. From the Visitor Center, head onto the path towards the Yorktown Historic District. The historic district begins at the Dudley Digges House. Buildings that...
    Read more