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Community, Things to Do

Local Vacations: Five Virginia Road Trips

July 23, 2026 by Elizabeth Krischer

Our summer road trip series continues, and this time we’re heading next door. Virginia has a wealth of experiences that everyone in the family will love. We’ve narrowed it down to five destinations so you can pick one or all of them—in one big road trip! 

Ponies at the ocean. A drive through the mountains. History under your feet. Find your ideal vacation in one of these Virginia getaways.

Arlington and Alexandria

Distance from Annapolis: About 40 miles or 1 hour of driving

Let’s start by crossing the Potomac. Both Arlington and Alexandria are worth visiting, and you don’t have to choose. Just a 15-minute drive will get you from one to the other. Both towns have storied pasts that are part of the history of the U.S. Alexandria has picturesque, small-town charm (which Annapolitans will appreciate), while Arlington is known for its nightlife. But there’s plenty to do for all ages.

Things to Do

  • Arlington National Cemetery: A visit to Arlington is not complete without paying your respects at Arlington National Cemetery. Arrive in the morning to either explore on your own or buy tickets for a tour. With more than 600 acres to traverse, a hop-on, hop-off tour is an easy way to maximize your time. You’ll see President Kennedy’s gravesite, the Tomb of the Unknown Soldier, Arlington House, and more. 
  • Climb UPton: For adventure-seekers, this three-level climbing structure has challenges for every skill level. Kids as young as five can get in on the fun as long as they’re accompanied by an adult. Then let gravity take over on the zip line or free-fall attraction.
  • Woodlawn and Pope-Leighey House: These two homes represent important aspects of history and architecture, 150 years apart. The Woodlawn home began as a plantation until it was sold to a Quaker family who turned it into a free labor colony. And the Pope-Leighey House is the only Frank Lloyd Wright home open to the public in the D.C. area. You can buy tickets to tour one or both of the homes. 
  • Torpedo Factory Art Center: Get up close and personal with some amazing artists in this center. This is not a traditional museum experience, but a collection of working artist studios. Plus, the building is home to the Alexandria Archaeology Museum, where you can learn about excavations of prehistoric, maritime, and Civil War artifacts.
  • Chessie’s Big Backyard & Our Special Harbour: Alexandria’s Franconia Family Recreation Area has accessible play spaces for kids of all abilities. The Harbour is a Chesapeake Bay-themed splash pad and spray park. Sensory-friendly Wednesdays add another opportunity to include all kids in the fun. And Chessie’s Big Backyard has a playground, a trail, and a treehouse!
  • Mount Vernon: George Washington’s home is not only a well-preserved house, but also a walk through history. Interactive exhibits, lush gardens, and friendly farm animals help visitors explore the estate like 18th-century folks. Wreath-laying ceremonies at both George Washington’s tomb and the memorial to people enslaved on the estate honor the lives of everyone who had a hand in the making of this country. Whether you have an interest in early American agriculture, history, or everyday life, there will be something for you.

Places to Eat

  • Breakfast: Good Company Doughnuts & Café, Kaldi’s Social House, Lightning Coffee
  • Lunch: Busboys and Poets, Bob & Edith’s Diner, or Westville
  • Dinner: Vola’s Dockside, Virtue Feed & Grain, or Chadwicks

Shenandoah Valley

Distance from Annapolis: 114 miles or 2.5 to 3 hours of driving

The mountain ranges of the East Coast include some of the oldest in the world. The Appalachian range, including the Blue Ridge Mountains, has been here for hundreds of millions of years. The drive is beautiful, with farms, wineries, forests, and—of course—sweeping mountain landscapes. You’ll be singing “Oh Shenandoah” all the way home.

Things to Do

  • Skyline Drive: Travel along the crest of the Blue Ridge Mountains by car to see a spectacular view. It’s within Shenandoah Valley National Park itself, so you can use it to get to a hiking trail, or the drive can be its own activity. According to the National Park Service, the entire drive only takes about three hours. However, you’ll want to leave time to make stops for taking lots of pictures.
  • Hiking: There are more than 500 miles of trails throughout the park. Both backpackers and day hikers will love the natural diversity and wildlife of the park. The Appalachian Trail from Georgia to Maine includes 101 miles in Shenandoah. For your visit, you can hop on the trail and meet a few thru-hikers before wishing them well on their way. 
  • Stargazing: The Big Meadows area of the park, near the (appropriately named) Big Meadows Lodge, has a perfect view of the night sky. The open field and higher elevation provide enough space to see thousands of stars. Wait until dark and join dozens of other stargazers for breathtaking views. 
  • Art and Entertainment: Whether you’re staying at one of the lodges or just visiting, you can join in on lessons and performances. There are classes on painting and traditional basket weaving. And a lineup of musicians and dancers will entertain and educate audiences. These are the perfect relaxing activities after a long day out in the wilderness.
  • Luray Caverns: Not far from the national park, Luray Caverns is an unreal wonder that kids will love. The paths are well-lit and well-paved, so you don’t have to leave behind your stroller. Tickets to Luray include visits to nearby attractions such as a historical toy museum, a motor museum, and a ropes course. But the caverns are enough of a reason to venture outside of the park.

Places to Eat

  • Breakfast: Rudy’s Diner
  • Lunch: Big Meadows Lodge
  • Dinner: Skyland

Williamsburg

Distance from Annapolis: About 190 miles or 3.25 hours of driving

An ideal location for active families with young kiddos, Williamsburg offers a mix of history and excitement, whether you prefer water slides or carriage rides. Be sure to leave plenty of room in your schedule for each family member’s preferred activity. The kids will get to ride roller coasters, then Dad can watch a reenactment, and Mom will get some time in the beautiful gardens before you continue your Virginia journey.

Things to Do

  • Colonial Williamsburg: Walk through early American history and learn about colonial life during the Revolution. And if you can’t get enough, the site of Jamestown is a short drive away. 
  • Busch Gardens: A full day of fun can be had at this theme park, with rides, games, shows, and more. There is so much to do, you could make this the only reason for your trip to Williamsburg.
  • Wagsters Magic Theatre: There are two kinds of people: those who think magic is lame and those who like having fun. Even the former will love the Wagsters shows, with both classic and new tricks. The intimate venue will give you the best seat in the house, wherever you are.
  • Yorktown Fishing Pier: No one needs a license for fishing off the Yorktown pier, even those from out of state. According to their website, there are abundant fish and other marine life to see—including dolphins! And there are any number of ships passing through. Bring your fishing rod or just take a walk to see the view.
  • Williamsburg Botanical Garden: Have a picnic and see the plants and pollinators on all two acres of the grounds. Volunteers working hard to care for the plants are also there for you to ask about tips and tricks for your own horticultural endeavors back at home.

Places to Eat

  • Breakfast: The Brunch Company, Colonial Pancake House, Another Broken Egg Café
  • Lunch: Shorty’s Diner, Fat Tuna Grill, Burgers on the Edge
  • Dinner: Second Street Bistro, King’s Arms Tavern, Amber Ox Public House

Virginia Beach

Distance from Annapolis: About 244 miles or 4.5 hours of driving

Perfectly located where the Atlantic meets the Chesapeake, Virginia Beach has enough activities and fun for all water lovers. It has a small beach town’s pace but a big city’s amenities. So if you’re not a “lie on the beach all day” kind of person (sometimes it’s not easy to relax!), you can get up and explore.

Things to Do

  • Virginia Aquarium: Some of your favorite marine critters are at the Virginia Aquarium & Marine Science Center. There are sharks, rays, sea turtles, river otters, and so much more. Get hands-on with their touch tank before letting your kids loose in the indoor and outdoor play areas. Or go climbing at their very own Adventure Park!
  • Dolphin Boat Tour: Also through the aquarium, a boat tour lets you see bottlenose dolphins traveling through these waters. (And if you decide to come back in the winter, they have whale-watching tours, also!)
  • Atlantic Park Surf: Perfect for those who are experts at hanging ten and those who have never touched a surfboard, you’ll have a blast at the Atlantic Park Surf wave pools.
  • Virginia Museum of Contemporary Art: Spend some time viewing all kinds of art from conceptual to meticulously handmade. Then create your own work in the family-friendly ARTlab.
  • Owl Creek Landing: Get an owl’s-eye view from the canopy and walk along the treetops. The view will be amazing right up until you take the long ride down…and it is long! In fact, Owl Creek Landing has the longest steel slide in America. Kids and adults (probably braver than me) will have a thrilling ride the entire way.

Places to Eat

  • Breakfast: The Egg Bistro (two locations), Doc Taylor’s Restaurant, Commune
  • Lunch: Hair of the Dog Eatery, Rick’s Cafe, Bay Local Eatery
  • Dinner: Icehouse Restaurant, Waterman’s Surfside Grille, Arbuckle’s

Chincoteague and Assateague

Distance from Annapolis: About 142 miles or 3 hours of driving

The beaches of Chincoteague and Assateague Islands are destinations for horse girls (and boys) everywhere. The wild ponies—or, to be more precise, feral ponies—have been on the islands for hundreds of years. But they aren’t the only reason to see this beach. Check out the wildlife, people, and even rockets that local adventurers will enjoy.

Things to Do

  • See the Ponies: If you visit at the end of July, you can witness the Pony Swim, where they are herded by Saltwater Cowboys from Assateague to Chincoteague. The website suggests sticking around until the final day, when most of the crowds are gone and the ponies return to Assateague at their leisure.
  • NASA’s Wallops Flight Facility: If you’ve had enough of seeing the ponies (which I doubt, but let’s pretend), you can see some rockets blast off. Watch large-scale launches and sounding rocket launches from the Visitor Center’s Launch Viewing Area. Bring a picnic blanket for an unforgettable experience.
  • Delmarva Discovery Center: The natural world and cultural heritage of the Delmarva Peninsula are on full display at this museum. There are reptiles to meet, a cypress swamp trail to traverse, and a kids’ room to play in.
  • Museum of Chincoteague Island: Learn about Chincoteague, or the “beautiful land across the water” as named by Native Americans. The Museum of Chincoteague Island has exhibits on local history from prehistoric to the 20th century. There are interactive exhibits including a touch table for kids.
  • Assateague Lighthouse: This lighthouse, originally built in 1833, is an impressive, red-and-white-striped landmark in the Chincoteague National Wildlife Refuge. While it is still used as a navigational aid by the U.S. Coast Guard, island visitors can climb up to the top. 

Places to Eat

  • Breakfast: AmaRin Coffee USA, Beach Road Round-Up, Sandy Pony Donuts & Açai Bowls
  • Lunch: Mr. Baldy’s Family Restaurant, Having a Meltdown, Pico Taqueria
  • Dinner: Blackfin Island Grille & Tapas Lounge, Barn to Beach Market and Deli, Ocean Deli

For families who love a road trip, you don’t have to travel far for both excitement and relaxation. Lovers of history, art, nature, and thrills will enjoy a vacation to any one of these spots. That’s why they say that “Virginia is for Lovers!” So make room in your calendar this summer for a trip to Virginia.

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Category: Community, Things to DoTag: road trip, trip, vacation, Virginia See all posts by Elizabeth Krischer

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