A three day weekend in Virginia Beach means three days of fun, sun and exploring all that our coastal city has to offer. From unbeatable outdoor adventure to unrivaled coastal cuisine, and everything in between, spend a long weekend with us in Virginia Beach for a getaway you won’t soon forget.
Whether you’re a history buff or just looking for an educational trip for the whole family, there’s no shortage of ways to experience history up close in Virginia Beach. From the landing place of America’s first European settlers to historic buildings and world-class museums, our roots in America’s past run deep here. With so much to do, a long weekend in Virginia Beach will certainly be one for the history books.
Day One | Explore America’s Beginning
Start your first day by exploring the doorstep of America in the Chesapeake Bay District. At the north end of Virginia Beach, located within the Fort Story military base, the Cape Henry Memorial Cross was placed in 1935 to commemorate the 1607 landing of English settlers who sailed across the Atlantic Ocean on three small ships: the Discovery, the Susan Constant, and the Godspeed. Upon landing, the settlers from the London Company erected a cross on the newly-anointed Cape Henry in gratitude of God and to affirm England’s claim to the area. After exploring several days, they travelled up the James River and established the first permanent settlement in the new world at Jamestown.
Just steps from the Cross stands the original Cape Henry Lighthouse, the first lighthouse authorized by the U.S. government, dating from 1792. It was also the first federal construction project under the Constitution, for an original contract amount of $15,200 (an additional $2,500 was required to finish the lighthouse). The lighthouse is open to the public and a breathtaking view can be enjoyed from its observation platform. It was designated a National Historic Landmark on January 29, 1964. In 2002 the American Society of Civil Engineers designated the lighthouse a National Historic Civil Engineering Landmark.
After a morning spent exploring these historic landmarks, head across Shore Drive to experience the prehistoric First Landing State Park, another registered Natural Landmark, which offers a glimpse into the enchanted forest the used to cover much of the area. The park consists of 2,888 acres that front the Chesapeake Bay, with 1.25 miles of beach and more than 19 miles of interpretive hiking trails through protected salt marsh habitat, freshwater ponds, beach, dunes, forest, tidal marsh and cypress swamp. First Landing is the most visited state park in Virginia and contains one of the most endangered habitat types in the world, the maritime forest community.
The trail center, accessed through the south entrance off of Shore Drive, is the main hub for accessing the nine interpretive trails that run through the park. Hikers can choose from nine hiking trails through the park’s seven distinct ecosystems, including the Cape Henry Trail. This six mile trail is the park’s longest, stretching from the northern border to southernmost entrance off of Atlantic Avenue, and is the only trail accessible to both hikers and bicyclists. For a scenic hike through the enchanting cypress swamps, Bald Cypress Trail offers a 1.5 mile loop, including several boardwalks and platforms overlooking the low wetlands, making for several great photo-ops.
Day Two | Take A Step Back to America’s Golden Age
Begin your day by taking a step back in time to our country’s Golden Era with brunch and a morning cocktail at the vintage naval-themed Anchor Allie’s Bistro, with a location in both the Chesapeake Bay District and Town Center. For a unique take on an omelet, we recommend their Bridge “Bomblette,” which combines seasonal local berries with creamy brie and a drizzle of honey, making for the perfect combination of sweet and savory. Their breakfast cocktails change regularly, but we have yet to try one we haven’t loved!
Continue the theme of the day by heading down to the Pungo area for a visit to the Virginia Military Aviation Museum. Take a ride on a vintage 1941 Boeing Stearman open-cockpit biplane or step even further back in time to the Jurassic Era with a stroll through their “Jerrassic” Park, named after museum owner, Jerry Yagen. Located in the Pungo agricultural district, the museum holds the largest private collection of 65 planes from the first 50 years of military aviation, and most of the aircraft have amazingly been restored to their original flying condition.
After a day at the museum, fuel up at The Bunker, at the Virginia Beach Oceanfront. This military-themed restaurant and taphouse comes from the people at Young Veterans Brewing Company, so you know the beer is good. This veteran-owned, military-themed spot is a must visit for veterans and non-veterans alike. As if the creative and tasty brews weren’t enough reason to visit, the WWII-themed artwork for each beer, prominently displayed on the walls, makes this worth the trip in its own right. It doesn’t hurt that the staff also knows their stuff and will get you set-up with the perfect beer for your preferences every time. We’d recommend the Pineapple Grenade Hefeweizen or the I Love Jet Noise Double IPA, but it’s really hard to go wrong with any of the beers here.
Day 3 | Discover the Virginia Beach of Yesteryear
Begin your last day the right way with breakfast at Doc Taylor’s, at the oceanfront. The old seaside doctor's office is cranking out delicious diner-style breakfast favorites that will get you off on the right foot. This spot is such a locals' favorite, that the menu features several items named for regular customers that have frequented the diner over the years.
Let your breakfast settle as you explore the most historic buildings on the boardwalk, like DeWitt Cottage, built in 1895. The cottage is now home to the Atlantic Wildfowl Heritage Museum, which exhibits artifacts from our wildfowling history and contemporary wildfowl artwork, such as decoys and decorative carvings. The museum also features volunteer carvers each day, so you can see how these works of art are created.
Another historic oceanfront building, The Virginia Beach Surf and Rescue Museum, is housed in a former U.S Life Saving Station which built in 1903 on the Virginia Beach Boardwalk. Today, the museum preserves our coastal city’s maritime history through exhibits on local surfing legends, super storms that have hit Virginia Beach, shipwrecks, local lifeguards and more.
Spend the afternoon exploring Virginia Beach’s role in our country’s heritage at by taking a peek into the day to day lives of our earlier residents. Learn about one of Virginia’s first colonists and see a dramatic turned staircase at the oldest home, Adam Thoroughgood House, circa 1719.
Down the road from the Thoroughgood House, the Lynnhaven House, circa 1725, is a stunning example of early Virginia vernacular architecture with several artistic design elements.
After the tours, unwind with a beer at Farmhouse Brewing. Our newest brewery, located in one of our older houses, comes from the folks at Back Bay Brewing, and brings a truly unique beer drinking experience to Virginia Beach. Operating out of a restored 1912 inland farmhouse, the Farmhouse is bringing locally-sourced brews and ciders to our coastal city. With tasting rooms upstairs and downstairs, food trucks, a farmers market and an acre and a half of gardens growing figs, blueberries, hops and other ingredients that will be used in their beers, this place has it all. Outside, pets are welcome and you can enjoy bocce ball, ladder golf, and cornhole, with stunning views of the farmhouse yard and the gardens, operated by Farmer John, formally of Pungo’s New Earth Farm.