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13 Cool Things to do Labor Day Weekend in the Chesapeake Bay Region

Labor Day Weekend fun is in visit Maryland's southernmost town. See 400 blue crabs compete in one of the most celebrated crustacean events in America, The National Hard Crab Derby & Festival in Crisfield, MD includes a parade and evening concerts.

Check out the latest livestock Maryland has to showcase, including horses, steer, goats, and cows at the Maryland State Fair in Timonium. The lunch suggestion is the crab patty - A sandwich that has a crab cake AND a soft shelled crab. Oh my! Then indulge yourself with deep-fried Berger cookies , red velvet funnel cakes, and deep fried Oreos.
Chesapeake Bay sounds include wildlife, boats, parades, sports fans, and the Monty Alexander Jazz Festival. Labeled one of the best festivals for Jazz, this Easton based festival adds the energy to Labor Day weekend.
Can’t wait for 2021’s America’s Cup (currently held by New Zealand)? Check out the Deal Island Skipjack Races & Island Festivalon August 31st – Sept 2nd. Deal Island is on the MD side of the eastern shore by the VA state line. Did you know that a Skipjack is the primary boat used for harvesting oysters from the Chesapeake Bay? Go check it out!

Time to get shakin’ with Groovin' By the Bay Concert Series. at Mill Point in Hampton, a free concert on the evening of Sept 1st.

Vertical Horizon, Cracker, and Moon Taxi lite up the stage at American Music Festival at Virginia Beach. With additional boardwalk stages this event offers every music genre.

Music and running goes hand and hand. I guess why Rock ‘n’ Roll is perfect for this half marathon. The annual Rock ‘n’ Roll Half Marathon is a world wide event that stops in Virginia Beach each year.

Hanging out at a former landfill? You would if it was a 165 acres with a mountain, lakes, playgrounds, a skatepark and walking paths. The world-renowned Mount Trashmore Park is an environmental feat and perfect for exploring during Labor Day weekend.

If you traveling the eastern shore this Labor Day weekend try to stop in to Smith Island (Maryland side) and try the Smith Island Cake. The unique cake arrangement and the number of flavors make the trip worth it.

The Chesapeake Bay’s pride and joy is the crab cake. As the summer winds down, make sure you enjoy the delicous dish at any dockside bar or seafood town.

Start the holiday weekend with a Friday happy hour Free Wine Tasting. The Virginia Beach Winery offers samples and tastings to delight everyone’s palette.

Sailing, boating, seafood, and maritime heritage are all on display as the Hampton History Museum exhibits “Hampton One: Working, Building, and Racing on the Water". This is a chance to explore the history of the Chesapeake Bay and the importance of the bay in Maritime.

As August concludes gather the last of local cucumbers, nectarines and peaches at your local produce stand. September will continue to produce beans, cantaloupes, eggplant, peppers, sweet corn, watermelons, and tomatoes.