Chesapeake, VA

Easy access to natural beauty and a great sense of culture are what attract people from all over the world to Chesapeake, Virginia. A hotspot for outdoor enthusiasts, foodies, and history-boughs, it’s easy to see why it’s the Commonwealth’s third largest city.

Boasting some of the best weather in the state, the Chesapeake region won’t disappoint when you’re looking to enjoy some time outside. Home to a large portion of the 167-square-mile Great Dismal Swamp, 3,000 acres of Lake Drummond’s inky surface, and stands of old growth forests - this place is an outdoor enthusiast’s dream come true. Trails that follow canals, bridges that span brackish lowlands, and quaint neighborhoods with a coastal feel will show you a side of Virginia that you never knew.

Get Outside in Chesapeake!

Top 10 Chesapeake Adventures
  1. Paddle the Dismal Swamp Canal Located just 12 miles from the city is the oldest continually operating man-made canal in the United States - first opened in 1805. This 22 mile long waterway was once part of a large-scale logging operation although today it is used primarily for recreation. And it’s a good thing because this navigable flat-water is beautifully quiet and holds countless species of wildlife for you to enjoy.
  2. Geocache in Northwest River Park The Northwest river runs through the southeastern corner of Chesapeake and on into North Carolina. The park can be found just off of Indian Creek Road, a short drive from town. With 763 acres, 66 campsites, 2 cabins and some modern amenities, this park offers a little bit for everyone. Choose from several different geocaching coordinates to explore the park and find hidden treasures.
  3. Canoe Lake Drummond Drive to the western entrance of Great Dismal Swamp, or find one of the feeder ditches to make your way by boat, to the highlight of Great Dismal - Lake Drummond. This natural lake is thought to have been formed by a meteorite, which may be why its bowl shape is so pronounced. Be sure to take notice of the massive bald cypress trees that mushroom from the water’s surface and keep your eye out for unique wildlife like alligators, black bears, and the southern flying squirrel.
  4. Hike the trails at the Chesapeake Arboretum (part of the VA Birding & Wildlife trail) No eastern adventure would be complete without being inspired by beautiful forests. The Chesapeake Arboretum, located 5 miles from town will give you a new sense of appreciation for old growth forests. A beautifully maintained trail system will have you wondering why humans cut down such beautiful organisms. Your eyes will be in the sky as you notice the many species of birds that call these trees home as you walk along an exclusive part of the VA Birding and Wildlife Trail.
  5. Run Bell’s Mill If a good sweat is more your speed then take time to visit Bell’s Mill Park, just a few miles from the Arboretum. A two and a half mile loop winds through open meadows and swampy wetlands giving you a good distance for a quick workout. If you’re a bit of a distance runner, make a couple of loops and link into some of the surrounding neighborhoods that line the Elizabeth River.
  6. Fish in the Elizabeth River. North of town is a public boat landing for the Elizabeth River where you can access the famed fishing spot and catch speckled trout. Ask any old-timer where the best fishing in town is and he’s likely to point you far from here - only to see you there at sunset. Be sure to take a look at the South Norfolk Jordan Bridge while your here as it spans the Elizabeth in great style.
  7. Walk the Dismal Swamp Canal Trail The earliest stories of adventure in the Dismal Swamp were on foot. Early in the Civil War many runaway slaves escaped to this boggy area as a refuge from ill-willed pursuers. Now you can take a first hand look deep into the dismal swamp from the comfort of a well-maintained trail while learning the history, and importance, of these biodiverse ecosystems.
  8. Fish from Bob’s Fishing Hole Get outfitted and find your way to the banks of a great little spot to watch ‘em rise. The Northwest River winds all through here and offers great bass, crappie, and catfish waters. Get your line wet and try to pull out a fish bigger than Bob’s - good luck!
  9.  Trek across the South Norfolk Jordan Bridge’s walkway The South Norfolk Jordan Bridge is an engineering feat that rises to 160 feet and spans the gap between Chesapeake and Portsmouth. This maximum height makes it the tallest bridge in coastal Virginia and its pedestrian walkway allows you to see, and feel, just what a marvel it is.
  10. Walk around Oak Grove Lake 65 acres of hardwood forest alongside wetland terrain make this park a gem so close to the city. Enjoy a mellow stroll around the lake or a picnic at one of the facilities. The crystal clear waters with sandy shorelines will make you feel as though you’ve escaped to another world - only to be back in Chesapeake within minutes.

In the Area

Explore Chesapeake, VA
  1. Big Ugly Brewing New to the Chesapeake area is Big Ugly Brewing. Serving their Split Window Saison, Sunbeam Blonde, Rockers IPA, Ape Hanger Stout, and The Magic Bus Berlinerweisse this brewery is quickly becoming a destination among the other craft brewers in the eastern shore. Suite 104, 1296 Battlefield Blvd S, Chesapeake, VA 23322 - (757) 609-2739
  2. Cutlass Grille This place takes barbecue to a whole new level. They call it Jamaican jerk and it lives up to its name. Prepare yourself to enjoy some of the best food you’ve had in your life. True to its Jamaican roots, this place meshes caribbean style with southern swagger. The place is rarely empty so go early and bring your appetite. 805 Battlefield Blvd N, Chesapeake, VA 23320 - (757) 382-0015
  3. Adventure Kayak Tours - If you’re looking for an adventure then these guys have you covered. Ocean, flat-water, and custom adventures built to suit your inclinations throughout coastal Virginia. Tours with Adventure Kayak have been known to spot dolphins, catch fish of all types, and explore some of the secret spots the locals won’t tell you about. Beginners and experts welcome with no group minimum, expect to get wet and to have the time of your life! 757-237-8776 ~ adventurekayaktours@gmail.com

Native Knowledge

Local Lore
  • “Hiking and trail running at Northwest River Park is a high adventure in a low elevation town. I like getting my shoes muddy here on the 6-mile outer loop around the park. It’s the best glimpse of the river’s wilderness you can get on two feet.”
    Shawn C. Callahan, Outdoor Programmer
    Chesapeake Parks
  • "Kayaking in Chesapeake provides the unique opportunity to take a step back in time. Witnessing first-hand the sights and sounds of an ancient eco-environment. Once spanning over 1 million acres, these Cypress swamps have harbored human cultures for over 13,000 years. Tracing the steps of George Washington in The Great Dismal Swamp should be "must do" on any adventurer's bucket list. Endless miles of historic, awe-inspiring waterways is the reason Chesapeake is Coastal Virginia's premier kayak destination."

    -Kevin Fonda, Owner
    Adventure Kayak Tours
  • “Kayaking and canoeing on Smith’s Creek and the Northwest River is the close to home wilderness experience that I seek out each spring. I like putting in at the Baum Road launch, part of Northwest River Park, for the 1.5-mile paddle to the river. This unspoiled river runs for miles west and south with little human development and lots to explore.”

    Shawn C. Callahan, Outdoor Programmer
    Chesapeake Parks