20 Adventurous Reasons to Stop In Chesapeake, VA

If you have only seen the road signs for Chesapeake, VA on your way to Virginia Beach or North Carolina’s Outer Bank, you don’t know what you’re missing.

Battlefield Museum in Chesapeake VA
credit Chesapeake CVB

Table of Contents

Why visit Chesapeake Virginia?

There are a wide variety of adventures to take in the coastal Virginia town of Chesapeake. Throughout the city, you can explore 22 miles of rivers, canals, and other waterways.

Enjoy a day of hiking, bird watching, or fishing at one of the city parks. There are plenty of opportunities to enjoy entertainment and the arts at Chilled Ponds and the Chesapeake City Park, or pop down for the Chesapeake Jubilee. 

credit Chesapeake CVB

History buffs will enjoy spending time along Chesapeake’s African American Heritage Trail, Great Bridge Battlefield, Chesapeake 9-11 Memorial, and the re-enactment of the Battle of Great Bridge.

Those who enjoy getting on the water can grab a canoe, kayak or paddle board, and take to the Chesapeake waterways. You can explore the off-the-beaten-path or join a group and Paddle for the Border to North Carolina.

The city of Chesapeake parks, historical sites, and entertainment venues can fill a few hours or a whole weekend. 

Eating crab in Chesapeake VA
credit Chesapeake CVB

Where is Chesapeake VA?

Chesapeake is one of the many cities that was once part of Norfolk County in the United States. Today, it is generally considered part of the metropolitan area that includes Virginia Beach, Norfolk and Newport News in South Hampton Roads.

KayaXpedition Line of Kayaks
credit Chesapeake CVB/ Angela Douglas Photography

Explore the Great Outdoors in Chesapeake

Great Dismal Swamp Canal Trail

Get some fresh air and enjoy hiking, jogging, horseback riding, or biking along the 8.2-mile multi-purpose trail, the old US Route 17, as it goes along the Dismal Swamp Canal. 

Along your journey, you will discover historical habitats. The historical park also has picnic areas to enjoy a picnic after exploring the trail.

The start of the Dismal Swamp Stomp in Chesapeake VA
credit Chesapeake CVB/ Angela Douglas Photography

Dismal Swamp Stomp Running Festival

In the spring, take part in the Paddle for the Border or the Dismal Swamp Stomp Running Festival.  They have a 5K and half marathon run along with a kid’s ½-mile run through the wetlands during the festival.  The festival features live music, awards, and yummy food.

Kayaking in Dismal Swamp

If you want to spend more time around Edgar Allen Poe’s “The Raven” inspiration, then head to Ballahack Road, where you can launch canoes, kayaks, and small boats to explore the Dismal Swamp that stretches to northeast North Carolina.

As you paddle the waterways, look for the Atlantic white-cedar and rare tupelo gum-bald cypress trees that make up about 20% of the forest.  For those not comfortable heading into the swamp by themselves, take a guided kayak tour with Adventure Kayak Tours.

The 112,000-acre wetlands in the Great Dismal Swamp provides undisturbed wildlife exploration, pristine natural habitats, a chance for foggy, mysterious photographs, and a haunting, beautiful landscape to explore.

credit Chesapeake CVB/ Stewart Ferebee Photography

Paddle for the Border

Be one of 300 participants who canoe and kayak for three hours along 7.5-miles from the Dismal Swamp Canal to the Virginia/North Carolina border on a Saturday in May. The trip is peaceful and elegant as you float past the Atlantic White Cypress trees, river otters, deer, and maybe even a black bear.

This historic waterway is full of rich history when George Washington first surveyed the area, and the canal was a refuge to slaves traveling along the Underground Railroad system.

Lake Drummond and The Dismal Swamp in the Great Dismal Swamp National Wildlife Refuge
Visit Suffolk VA

Lake Drummond

In the Great Dismal Swamp National Wildlife Refuge center, you will find tall cypress trees surrounding the shallow Lake Drummond. This lake is the perfect canoe or kayak destination.

The fishing is excellent, the lake is picturesque, many birds come to the lake to feed and drink, and the sunsets are magnificent. 

Fisherman will be reeling in catfish, perch, and crappies while the bird lovers enjoy sighting snow geese and tundra swans in the winter, and great egrets and blue heron in the summer.

Note: Spring is the best time for crappie fishing.

Sailing on the Northwest River Park in Chesapeake VA
credit Chesapeake CVB/ Stewart Ferebee Photography

Northwest River Park

Along the Northwest River in southeast Chesapeake, the 763-acre Northwest River Park has a lot to offer visitors. 

For nature lovers, put your walking shoes on and enjoy flora and fauna along the eight miles of hiking and biking trails. There is also an equestrian area for horse owners looking for a new spot to take a stroll.

Birds along the Northwest River

This area of Chesapeake is home to more than 200 species of birds. Spring and summer are the perfect time to see peewees and bluebirds, while during the fall and winter, the dark-eyed juncos and song and fox sparrows are abundant. 

Throughout the year, keep your eyes peeled for hawk or bald eagles along the Virginia Birding and Wildlife Trail.

Northwest River Fishing and Boating

The park rents both canoes or paddle boats, making it easy to get on the water. Smith Creek and Indian Creek are great for paddling and offer boaters a beautiful sunset opportunity.

From the banks or boat, enjoy fishing the stocked six-acre lake.

Boating on Lake Lesa in Northwest River Park Paddle
credit Chesapeake CVB

Activities in Northwest River Park

The park also has various picnic areas, a playground, horseshoe pits, a disc golf course, and the Dude Ranch mini-golf course to keep you entertained all day long.

Camping in Northwest River Park

To extend your stay, pitch your tent at one of the 66 campsites or rent one of the two cabins.  At night enjoy searching the dark sky for stars and planets. 

If the time is right, you can join the Back Bay Amateur Astronomers’ Sky Watch monthly meeting at the Equestrian Area.

The Visit Chesapeake website’s events section has more information and a schedule of events for the park.

Great Bridge Lock Park in Chesapeake VA
credit Chesapeake CVB Angela Douglas Photography

Great Bridge Lock Park

Great Bridge Lock Park is a 19-acre park overlooking the intersection of the Elizabeth River and the Albermarle and Chesapeake Canal. This network of waterways is part of the Intercoastal Waterway that boaters use to get from Maine to Key West, FL.

Along the shore, there are interpretive signs that explain the lock system. Throughout the year, this is a great place to view yachts passing through.

The park offers visitors a two-lane boat ramps, walking trails, picnic shelters, and a playground.

credit Chesapeake CVB

Deep Creek Park

The Deep Creek Park is a great spot to stop and enjoy a picnic lunch and let the kids run for a while.  The park also has an ADA Accessible playground for children with disabilities.

The picnic area has shelters and grills to roast up a few hot dogs and hamburgers when you get hungry.

You can also hike the one-mile trail that connects to the Dismal Swamp Canal Trail along the park’s perimeter.

This park is dog-friendly.

credit Chesapeake CVB

Chesapeake Park

Chesapeake Park, or simply City Park, encompasses 90 acres of which two-thirds is open space for flying kites, running around, and enjoying a friendly game of flag football.

Throughout the year, the park is home to outdoor festivals and concerts like the Chesapeake Jubilee and Chesapeake Park Whisper Concert Series.

The park also has a great skate park to test your latest moves, the Fun Forest playground, a dog park, and horseshoe pits to see who can get the most ringers.

Chesapeake Jubilee in Chesapeake VA
credit Chesapeake CVB/ Angela Douglas Photography

Chesapeake Jubilee

The Chesapeake Jubilee is a vast 4-day festival that includes the Kiwanis Club of Chesapeake’s Annual Shrimp Feast and the world-renowned Zambelli fireworks.

Since 1983, live entertainment, carnival rides, and games galore have attracted locals and visitors alike.

Fun Forest

When the kids need a break from visiting museums and the beach, head to the Chesapeake Park’s three-acre Fun Forest, where children can play and imagine until their heart is content.

The playground offers children a shaking bridge, swings, slides, paleontologist Fossil Dig site, and underground telephones to strengthening their coordination and motor skills.

Turkey at the Hickory Ridge Farm
credit Chesapeake CVB/ Stewart Ferebee Photography

Hickory Ridge Farm

Hickory Ridge Farm is an 18-acre, family-owned farm that has a petting zoo and delicious seasonal produce.

You can visit and pick strawberries in the spring, grab summer produce from June – August, and pick up Virginia pumpkins in the fall.  They also sell local honey. 

Gum Tree Farm

The children in your family will love visiting the animals at Gum Tree Farm. Across the farm’s 50 acres, they will be able to see the friendly pigs, goats, sheep, ducks, turkeys, cows, a horse, and a donkey.

Learn more about how the farm works by taking a tour that explains how the farmers dye wool and the farm’s history. Also, learn about how the farm is producing fiber from fibrous plants.

credit Chesapeake CVB/ Angela Douglas Photography

Chesapeake Arboretum

In the center of Chesapeake, VA, the Chesapeake Arboretum sits on this 48-acres encompassing part of the Virginia Birding and Wildlife Trail. It is one of Virginia’s treasures and nature’s classrooms filled with flora and fauna, including the antique rose garden, where you can learn more about the environment and horticulture through the plant displays.

As you stroll around the property’s three miles of trails, enjoy the fragrant themed gardens, 18th-century Calem Williamson farmhouse, Lake Hughes, and a picnic area.

Chesapeake Battlefield Overlook in Chesapeake VA
credit Wendy Debman

Explore Chesapeake’s History

Great Bridge Battlefield and Waterway Museum

In commemoration of the historical Battle of Great Bridge, this museum and battlefield located along the Intracoastal Waterways, offers a beautiful Historical Pathway with interpretive markers detailing the American Revolution battle, a museum and visitor center, and an outdoor auditorium.

The museum features both changing exhibits and a permanent gallery.

There is a monument in remembrance of the Patriot soldiers who lost their lives here at the park entrance.

To learn more about Virginia’s first American Revolution land battle, take one of the free docent tours the park offers daily.

Visit during December to see the recreation of the 1775 Battle of Great Bridge.

The Cornland School in Chesapeake VA
credit Cornland Foundations

African American Heritage Trail

Explore the incredible history of African men and women who passed through Chesapeake during the Revolutionary War and Civil War, and along the Underground Railroad, all while listening to their stories on the companion podcast.

This self-guided driving tour begins at Battlefield Park, where you learn about the resilience and heroism that continues to the historic 1700s historic community of Cuffeytown as you walk in their footsteps.

Stops along the trail
  • Battlefield Park
  • Unknown and Known Afro-Union Civil War Soldiers Memorial
  • Dismal Swamp Canal
  • Superintendent’s House
  • Cornland School
  • Cuffeytown

Battle of Great Bridge

During an annual two-day December event (normally the first weekend in December), come to Battlefield Park South to watch the re-enactment of the Revolutionary War’s Battle at Kemps Landing and the Battle of Great Bridge. 

This event retells the battle story of how the Continental Army drove the British government from the colony to claim Virginia.

Step back in time with war encampments, character portrayals, demonstrations of early American trades, and children’s activities on the original Battle of Great Bridge site.

There is a Daughters and Sons of the American Revolution wreath-laying ceremony on Saturday at 11:00 AM that begins at the Great Bridge Battlefield & Waterways History Museum at Battlefield Park.

The re-enactment event is free to attend.

Chesapeake 9-11 Memorial

Chesapeake has a memorial on City Park Drive where locals and visitors can pay respect to those who perished in the 9/11 attack.

A World Trade Center beam was used to create the memorial.  You will also find some limestone from the Pentagon and rock from Shanksville, PA at the site.

Places Indoors to Visit in Chesapeake

Chilled Ponds

There is no better way to spend a hot summer day than than on the ice at Chilled Ponds. The 90,000 square feet Ice Sports Complex has open skate times throughout the day.

Chilled Ponds is the practice facility for the ECHL Norfolk Admirals and local youth and adult leagues.  They also host birthday parties and have a learn-to-skate program.

Chesapeake Planetarium

Inside the Chesapeake Municipal Center is Virginia’s oldest planetarium. Guests can explore galaxies, the planets, and our solar system during shows.

NOTE: Check the planetarium’s schedule for opening dates, shows times, and when telescope observation times are available.

Campfire at Northwest River Park in Chesapeake VA
credit Chesapeake CVB

Camping in Chesapeake, VA

Chesapeake Campground

Pitch your tent or pull your camper into one of more than 100 campsites at the Chesapeake Campground. They offer a range of sites, from tent sites to full hookup sites.

The campground makes the perfect home away from home with its mini-golf course, pony rides, basketball and tennis courts, exercise room, and a golf driving range. You can also rent a bike or canoe to explore the area by water.

The camp store has all the provisions you will need, including snacks, CDs, games, and a few souvenirs.

Steward RV Campground

* Only open to active and retired military *

Steward RV Campground is a military campground open to all active duty, retired military, National Guard, Reservists, and DoD Civilians.

The campground has 14 sites with either partial or full hookups. Current and former military personnel can enjoy a stay here and take advantage of the picnic pavilions, fitness center, volleyball courts, and bowling center.

Each site comes with a grill and picnic table.  The campground does have restrooms with showers.

Pets are welcome.

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