Virginia Beach is always up for a good time, especially during holiday weekends like Labor Day weekend. This year, Labor Day will be celebrated on Monday, September 4, and there’s plenty of fun to be had leading up to it. This Labor Day weekend, bask in a “runners high” at a 10-mile race along the boardwalk, explore the outdoors, take in contemporary art or sip craft cocktails on a rooftop with friends. Whatever your vibe, here are eight things to do in Virginia Beach over Labor Day weekend 2023 that you won't want to miss.


Get a Running Start at the Chartway Virginia Beach 10 Miler & 5K  

Head into Labor Day weekend with a running start at the Chartway Virginia Beach 10 Miler & 5K. On Saturday, September 2, the event starts with a 5K along the Oceanfront. If you’re looking for a bigger challenge, register for the 10-mile run on Sunday, September 3, when the route will take you past iconic Virginia Beach landmarks such as the King Neptune Statue and the Atlantic Avenue Ferris Wheel, crossing the finish line close to the historic pier. You can even register for both races as part of the “Live the Life Challenge.” Both runners and walkers are welcome. To top off the fun, each day will feature a post-race celebration with live music, cold beer and good food. 

Chartway 10 Miler


Have Brunch at Rockafeller’s Restaurant  

Perhaps your idea of a great vacation morning starts around 11 a.m. with some delicious food and a view. If so, head to Rockafeller’s Restaurant for Sunday Brunch this Labor Day weekend. Order fresh seafood dishes such as the Rock’s Seafood Omelet with shrimp and bay scallops, Crab Eggs Benedict, She Crab Soup, and Shrimp Hushpuppies – a playful take on a Southern classic. Ask for a seat outside on the deck to watch as boats come and go in Rudee’s Inlet.  

Rockafeller's Restaurant


Enjoy Beach-Side Entertainment at Live! On Atlantic  

Experience the night come to life along the picturesque Oceanfront resort area with Live! On Atlantic. See sidewalks and streets become stages for performance artists, magicians, jugglers, musicians and more. Although Live! On Atlantic occurs takes place almost every night, Labor Day weekend is sure to hold plenty of fun surprises around every corner and is suitable for visitors of all ages.  

Live! on Atlantic Oceanfront American Music Festival



Enjoy Rooftop Drinks at O Bar

Nothing says “long weekend” quite like a relaxed evening in a rooftop garden enjoying delicious drinks with your besties. Head to Orion’s Roof Garden & Dining and revel in panoramic rooftop views overlooking the Atlantic and Chesapeake Bay as you sip specialty cocktails, like a Japanese Old Fashioned (a classic with a twist) – or if you’re a fruity drink lover, the bourbon-based Blackberry Smash with blackberry, yuzu and mint. Orion’s is located atop the Marriott Virginia Beach Oceanfront and reservations are required through OpenTable

colorful asian cuisine played with two hands reaching for food with chopsticks


Explore Local Waters by Kayak  

Is a day spent outside on sparkling waters ever a bad day? You know the answer to that, so make a plan to explore local waters on one of many Virginia Beach kayak tours. If a calm day paddle sounds ideal, book with Chesapean Outdoors, which offers a tour launching from First Landing State Park, and take in the scenery of Broad Bay and Linkhorn Bay as you paddle your way through quiet waters. If you’re hoping to spot marine life during your trip, try Kayak Nature Tours and head to a prime location for dolphin spotting.  

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Tap into Your Daring Side at The Adventure Park at Virginia Aquarium 

At The Adventure Park at Virginia Aquarium, guests can live life on the edge – the edge of a zipline platform, that is. The park, adjacent to the Virginia Aquarium & Marine Science Center, offers 17 treetop trails, 33 ziplines and over 250 different adventure challenges like low-rope and high-rope courses, aerial obstacle courses and tree swings for the little ones. This Labor Day weekend, opt for a family challenge and test your limits at this thrilling attraction. 

tree top adventure park at dusk with glowing purple lighting


Get Artsy at the ViBe Creative District

Bring out your artsy side this Labor Day weekend at ViBe Creative District, a unique arts and culture hub lined with art shops by local artists, restaurants and larger-than-live wall murals. Snap a photo or two by a colorful public art piece or head to the nearest coffee shop, such as Bad Ass Coffee of Hawaii or Three Ships Coffee, for a caffeine boost or sweet treat. Don’t leave without stopping into a few artisan shops like Igor’s Custom, which offers impressive hand-painted signs or Jars of Dust, where you can find handcrafted stoneware ceramic pieces.

Artist: TALENT


Explore the Military Aviation Museum 

Experience history take flight at the Military Aviation Museum in Pungo, one of the world’s largest collections of World War I and II military aircraft. The museum allows history and aviation buffs the chance to get up close and personal with over 50 aircraft over its 130-acre property, which is designed to mimic an actual airport facility. The museum offers group tours, story time for children, flight demonstrations and even offers open cockpit flight experiences on weekends for those looking to take their Labor Day experience to thrilling heights.  

man holding a boy looking at an airplane outside at a museum