Itineraries

How to Spend Your Labor Day Weekend in Virginia Beach

Crowd at an outdoor festival by the ocean, featuring a statue and a skateboarding ramp, with tents and event signage visible.

We love it when holidays grant us the opportunity to extend our weekend fun, and Labor Day brings with it an opportunity to squeeze in one last taste of summer. With plentiful weekend-long experiences sure to fill your (sand) bucket, you won’t lack in options. Whether you visit us for a day, for the weekend or for an extended getaway, we hope you enjoy mixing and matching the experiences of your choice from our picks below.

A plate of a dozen oysters on ice with a lemon wedge and a small cup of sauce in the center.
A plate of a dozen oysters on ice with a lemon wedge and a small cup of sauce in the center.

Friday, August 29

It’s 5 o’clock somewhere, and there’s a work week behind you and worth toasting to. So, find your Virginia Beach happy hour and get the long weekend started! 

Want to dive right into beach mode? Kick things off in elevated coastal style with handcrafted cocktails, shareable plates and plenty of oysters at The Atlantic on Pacific, or toast to the weekend beachside at Tulu Seaside Bar & Grill. 

Plan to wind down your evening at the Virginia Beach Oceanfront to enjoy Live! On Atlantic – free live performances and entertainment across various Atlantic Avenue parks.

 

Beach scene with a large Neptune statue holding a trident, a boardwalk with palm trees, and people walking or lounging on a sandy beach by the ocean.
Beach scene with a large Neptune statue holding a trident, a boardwalk with palm trees and people walking or lounging on a sandy beach by the ocean in the Oceanfront region in Virginia Beach.

Saturday, August 30

Kick off your first full day in Virginia Beach with a quintessential VB brunch at Doc Taylor’s, a one-time doctor’s home serving up delicious comfort breakfast and lunch food, bloody Marys and mimosas, just footsteps away from the Oceanfront beach.

Once you’ve fueled up with some yummy food, spend the day basking in the sun and enjoying the warm waters and calm waves of the Atlantic Ocean. When hunger strikes, head to VB’s favorite local sandwich shop, Taste Unlimited, and order yourself the North Ender to lunch like a local. Make your way back to the sand with a ride on a four-wheeled surrey; you’ll burn off some lunch and take in the Virginia Beach Boardwalk in a classic (and fun) way! 

When the sun starts to set, the real show begins. This Labor Day weekend, grab your spot on the sand and soak in free live music all weekend long as part of the Oceanfront Concert Series season finale. National acts like Gin Blossoms, Better Than Ezra and Sister Hazel will take the stage at oceanfront parks, filling the night air with everything from rock hits to nostalgic sing-alongs. Bring your beach blanket or chair and settle in for an unforgettable evening of music by the sea — every night starting at 7 p.m.

A marsh landscape at sunset with still water reflecting a pink and purple sky, surrounded by grasses, trees, and fallen branches.
A marsh landscape at sunset with still water reflecting a pink and purple sky, surrounded by grasses, trees, and fallen branches.

Sunday, August 31

Want to change up your beach scene – or your Sunday Virginia Beach scene altogether? We’ve got you covered.

Gear up for the day with an invigorating hike through preserved marshland dotted with Bald Cypress Trees adorned with Spanish moss at First Landing State Park. Then, grab a Honey Cinnamon Latte and a tasty bite at nearby American Brew before strategizing your spot in the sand at the Chesapeake Bay Beach. The Chesapeake Bay offers two miles of beaches to enjoy, spanning from the Lynnhaven Inlet to the Chesapeake Bay Bridge, so take your pick! And be sure to leave plenty of time on the itinerary for a seafood lunch (or dinner) at one of the nearby seafood restaurants serving up their fresh menus dockside.

Want to stay away from the beach altogether but still want to enjoy some traditional Virginia Beach fun? Embark on a Mural Walking Tour throughout the ViBe Creative District to take in colorful and thought-provoking murals created by local artists. Prefer to soak up the local culture indoors? Check out the last few days of the Virginia Museum of Contemporary Art, where admission is always free.

In the evening, soak in the uptown vibes at the Virginia Beach Town Center. Enjoy a classic martini at Twist then grab a tasty bite at one of Town Center’s multitude of restaurants and bars, including Three Notch’d Brewing Co., Cantina Laredo, Bravo Cucina Italiana, Keagan’s Irish Pub and so much more, before winding down your Friday with laughs at the Funny Bone Comedy Club, featuring comedian and actor Don “DC” Curry for a weekend-long special engagement.

 

Aerial view of a coastal town with a row of houses, wide sandy beach, and calm ocean under a clear sky.
Aerial view of a coastal town in Sandbridge with a row of houses, wide sandy beach and calm ocean under a clear sky.

Monday, September 1 – Labor Day

Change up your pace today with a scenic drive through the lush farmland of Pungo and onto Little Island Park in Sandbridge. Lay on the beach, walk along the ocean’s edge on the Little Island Pier or ride fat tire bikes on the sand (you can rent them nearby from Surf and Adventure Co.). 

We have a feeling this might be one of the most relaxing Mondays you’ve spent yet. Cheers to that!

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