Labor Day weekend may mark the unofficial end of summer, but there is still plenty of time to make the most of the season in Chesapeake. From live music under the stars and outdoor adventures to local history and family fun, the long weekend is a perfect excuse to get out and explore.
Whether you're planning a weekend getaway or looking for something close to home, here are a few ways to spend Labor Day weekend in Chesapeake.
Kick Off the Weekend with a Walk Through History
Start Saturday morning where history happened with a Battle Walk. Follow in the footsteps of the Battle of Great Bridge and learn about the first major Revolutionary War armed conflict in Virginia and the role it played in the fight for independence.
The free guided walk takes place Saturday, September 5, from 9:00 to 10:30 a.m. Registration is required.
While you're in the area, make time to explore the Great Bridge Battlefield & Waterways Museum and Battlefield Park along the Atlantic Intracoastal Waterway.
Spend the Day on the Water
Soak up one more summer adventure on Chesapeake's waterways. Grab a kayak, canoe or stand-up paddleboard and explore some of the city's scenic places to paddle.
At Northwest River Park, visitors can get out on Lake Lesa or spend the day exploring the park's trails, fishing areas and other outdoor activities. If you are new to paddle sports you can book a kayaking excursion with Adventure Kayak Tours. This guided tour include kayak or stand-up paddleboard, instruction, and the history of some of Chesapeake's most beautiful spots.
Already love getting out on the water? Make your Labor Day adventure count toward Paddle the Peake, Chesapeake's paddling passport. Check in at participating locations as you explore the city's waterways and work your way toward rewards along the way.
Look to the Stars
Keep your Saturday adventure going after the sun goes down with Skywatch at Northwest River Park. The Back Bay Amateur Astronomers invite visitors to spend the evening viewing stars and planets through telescopes in the park's Equestrian Area.
Skywatch begins around sunset on Saturday, September 5, and is free and open to the public. The program is weather dependent, so be sure to confirm before heading out.
Step Into Chesapeake’s Past
Make history part of your long weekend with a visit to Chesapeake's Historical Village. Explore stories that span thousands of years, from the region's Indigenous history and the development of the Dismal Swamp Canal to maroon communities and Chesapeake's African American heritage.
The six-acre site brings together indoor and outdoor experiences, including historic structures such as Cornland School, one of Chesapeake's oldest surviving Black schoolhouses.
Pair your visit with other historic sites around Chesapeake for a weekend that connects local stories to the people and events that helped shape the region and the nation.
Bring the Family Along
Looking for something the whole family can enjoy? Chesapeake has plenty of options.
Head to Fun Forest at Chesapeake City Park for an outdoor adventure, lace up your skates at Greenbrier Family Skating Center, or challenge the family to a few frames of bowling at Lucky Strike Chesapeake. For a slower pace, pack a picnic and explore one of Chesapeake's parks or trails.
With outdoor recreation and plenty of indoor options, you can keep the family entertained no matter what the weather brings.
End the Weekend with Symphony Under the Stars
One of Chesapeake's favorite Labor Day weekend traditions returns Sunday, September 6, when the Virginia Symphony Orchestra takes the Bagley Stage at Chesapeake City Park for Symphony Under the Stars.
Bring a blanket or lawn chair, find a spot on the lawn and enjoy an evening of live music beneath the stars. Food trucks will be on-site if you'd rather pick up dinner while you're there.
Parking and concessions open at 6:30 p.m., with the concert beginning at 7:30 p.m. Admission and on-site parking are free.
Make a Weekend of It
Three days means plenty of time to explore more of Chesapeake. Grab a bite at a local restaurant, browse local shops, hit the trails or spend a little more time on the water.
However you choose to spend the long weekend, Chesapeake has plenty of ways to squeeze a little more fun out of summer before fall arrives.
Explore more Chesapeake events and start planning your Labor Day weekend.
