15 Things to Do This Labor Day Weekend on Virginia’s Eastern Shore

Are you ready to enjoy a long weekend of fun on Virginia’s Eastern Shore? As the perfect end to a long summer, you can enjoy some of the best things to do around Virginia’s Eastern Shore this Labor Day weekend.

Enjoy a concert & LOVEFEST in the park in Cape Charles

This weekend, enjoy music from The English Channel as well as all the festivities of LOVEFEST in Cape Charles Central Park! A great way to enjoy your Saturday evening.

Take a guided ecotour

Ready to explore the incredible nature on Virginia’s Eastern Shore? Hop on an ecotour with one of our incredible guides to not only see the beauty of our area, but learn from them about the ecosystem, the history, and even personal stories of their adventures through our waterways. According to our Locals’ Choice competition, the locals’ favorites are Burnham Guides, Captain Barry’s Back Bay Cruises, and Cowboy Cruise Co. 

Dive into Eastern Shore History

Although it may seem unassuming, the Eastern Shore of Virginia is one of the nation’s oldest areas and many important historical figures called this peninsula home. Learn all about it at our museums and historical sites! Explore our Museums

Try a new food truck

Our food truck scene on Virginia’s Eastern Shore has exploded over the summer! Try one of our incredible food trucks and you just might find your new favorite food! Check out places to eat on the Shore.

Take your adventure to new heights on a hang-gliding experience!

What better way to experience the Eastern Shore than from the air? Check out Virginia Hang Gliding and explore the Shore from the sky!

Enjoy fine dining at one of our incredible restaurants!

Experience incredible dishes in the most beautiful setting on Virginia’s Eastern Shore! Check out our Local’s Choice 2024 winners to find our local’s favorite spots to eat.

Walk one of our small towns

Our small towns are perfectly walkable! Throw on your walking shoes and explore our towns on foot. Enjoy our small businesses, beautiful parks, waterfront views, and stop in to one our museums! Check out this ESVA map to guide you on your wanderings.

Find your new favorite ice cream flavor

Each of our towns has their own creamery. Check them out and you just might find your new favorite flavor! Our locals’ top picks are Island Creamery , Brown Dog Ice Cream, and Mister Whippy.

Enjoy a craft beer at one of our local breweries

Our beautiful peninsula is the perfect place to create incredible beer. Experience Cape Charles Brewing Company on your next visit and sample a flight of flavors inspired by the Shore!

Go sailing

Soak in the last of summer on the beautiful Schooner Windsong sailboat out of Cape Charles!

Try our local’s favorite tacos

With so many variations to this classic comfort food, you can’t go wrong with tacos! Try our locals’ favorite spots on your next visit. Our locals’ top three spots for tacos on Virginia’s Eastern Shore are Pico Taqueria, Lily’s Little Mexico, and Taqueria El Ranchito. Ready to explore taco trucks around the Shore? Check out our Taco Trucks Trail!

Enjoy a picnic on the beach

Is there anything more romantic? Grab delicious foods and drinks from our specialty gourmet shops (our locals’ favorites are Whiteraven’s Nest, North Street Market, and Wine, Coffee, and Gourmet or check out more places to shop here) and head to one of our gorgeous beaches for a picturesque afternoon.

Shop at a farmers and artisans market

Enjoy the best of our local farmers and artisans at our local markets! Shop at our locals’ choice top three – the Chincoteague Island Farmers and Artisans Market, Quail Cove Farms,the Onancock Market!

Cross a state park of your bucket list

Kiptopeke State Park is one of the most unique and varied state parks you can think of! With the Hawkwatch platform, trails, playgrounds, the beach, concrete ships, fishing, and more available to visitors, there is so much to enjoy!

Wrap up your trip with an incredible ESVA sunset

What’s better than a sunset in paradise? End your trip on a high note with a beautiful ESVA sunset! Find spots on the coastline to watch a sunset here.

While you’re adventuring around Virginia’s Eastern Shore, be sure to tag us in your photos and videos and use #visitesva to share.

Want to keep track of all of your wanderings? Use our Labor Day bucket list to cross off each stop on your way around the Shore. You’ve got a great weekend ahead of you – happy exploring!