When it comes to summer fun, consider taking a day trip or two and experience the Main Streets of Virginia’s small towns. Quaint shops, unique dining establishments and more await you as you explore and rack up family memories. Here are a few towns with Main Streets worth checking out

 

Gloucester Village

Gloucester Village is steeped in history, with a historic courthouse dating back to the late 1600s. As you stroll along Gloucester’s Main Street, be sure to stop and admire the wall murals throughout the area presented by The Cook Foundation. Mural images run the gamut, depicting Black History, the life of Pocahontas, and nature, including waterfowl and daffodils. 

Main Street has more than two dozen retail shops that range from antiques and art to flowers, jewelry and boutiques. When you need to fuel up, try Lulu Birds Kitchen, a scratch kitchen that serves “eclectic American” dishes including salads, steak, seafood and pasta. The kids and kids-at-heart, of course, will also want to stop at Sweet Tooth Café and Bakery for cupcakes or ice cream (or both!). “We have Northern Neck Popcorn Bag here too, which is always a family favorite,” says Jenny Crittenden, executive director of Gloucester’s Main Street Preservation Trust. Grownups, meanwhile, might also wish to pop over to Gloucester Brewing Company for happy hour.

Staunton

With its scenic views and unique buildings and landscape designs, Staunton’s Main Street was once honored by Architectural Digest as one of the “Most Beautiful Main Streets Across America.” The Historic Staunton Foundation offers guided architectural walking tours each Saturday April through October, or you can explore the area on your own with Traipse, a free phone app that will provide you with information about various sites in the historic business district. 

Recommended stops for your family during your visit include Pufferbellies, a children’s toy and bookstore; Yelping Dog Wine bar, which specializes in gourmet grilled cheese; and The Split Banana. “Who doesn’t like grilled cheese?” says Kathy Moore, a public relations representative for Staunton. “The Split Banana is also a great place. They have fresh, homemade gelato in great flavors. There is always a line out the door.”  The Staunton Music Festival, focusing on classical music, returns in-person in August.

Culpeper

The central location of Culpeper, the intersection of Davis and Main Streets, has been home to a lunch counter and café since 1928. “Today’s Frost Café still uses the counter and soda fountain from the original Gayheart Drug Store and Luncheonette,” says Paige Read, director of Economic Development & Tourism. “Set out from Davis and Main to explore shops that offer antiques, refurbished furniture, old-time sweets, fresh-baked treats and a whole lot more.” 

Read recommends stopping by La Bee Da Loca, where Felecia Chavez shares her experiences as a beekeeper. Upstairs, the shop is dedicated to telling the story of the honey bee, while downstairs, guests can buy honey and bee-related products as well as pieces from local artisans. “Kids love seeing the hives hard at work,” Read says. 

Meanwhile, one of Culpeper’s popular dining establishments is actually three restaurants in one: It’s About Thyme, offering European cuisine in a casual atmosphere; Thyme Market, which carries an extensive list of market-style selections; and The Cooper Fish, which serves custom prepared fresh catch seafood. 

Follow that up with a scoop of ice cream at Scoop on Davis, an old-time ice cream dip shop. More adventurous families might want to consider heading over to State Climb for some rock climbing, or Rockwater Park, where you can hike or play disc golf. The park also has an obstacle course, a climbing boulder and a splash pad for little ones.

Bedford

Bedford is known for the National D-Day Memorial, and as the town suffered the largest loss per capita of soldiers during the World War II D-Day invasion. The Bedford Boys Tribute Center on Main Street houses many personal artifacts of those soldiers. “It’s a moving place to learn the more personal stories of our soldiers that were lost, and the town they left behind,” says Nicole Johnson, director of Tourism. 

Also on Main Street, Johnson suggests visiting The Blue Lady Café and Ippolito Candy. “The café features sandwiches and salads and is a popular lunch destination,” Johnson says. “Ippolito Candy features handmade chocolates, made right there in the store. They make custom chocolates, candy and cakes. They go all-out with decorating for every holiday.” 

If you prefer Italian, there is the family-friendly Bella Italia, and Magic Ice Cream has a large deck with picnic tables and umbrellas. Bedford’s Main Street is also home to the Bedford Museum & Genealogical Library and the Bedford War Between the States Museum. 

Every September, the town hosts Centerfest, one of Virginia’s largest street festivals with vendors, food, kid’s activities, live music, and more! And, like many towns, Bedford also has the famous Virginia LOVE sign.

Ashland

Train enthusiasts will have a field day visiting downtown Ashland, located just outside of Richmond. Railroad tracks can be found down the center of the town’s main drag, and the visitor center is housed inside the train station. Ashland hosts a variety of events around the train tracks, including a Halloween event, the Light Up the Tracks Christmas Village and Ashland Train Day. 

Ashland Museum is home to a fully restored 1926 C&O red caboose, while the town also boasts The Depot, a restored historic venue and community event space. Other attractions include Bell Book & Candle, which offers a selection of books on the historic rail and Virginian history as well as a variety of children’s books, and The Caboose Market & Café along the railroad tracks, which has a seasonal menu of farm-to-table fare and carries a selection of beverages, locally made products and a variety of cheeses. 

Animal lovers might want to drop by Changing Reins, which specializes in equestrian equipment, apparel, and accessories and more, or the Fin & Feather Pet Center pet store. 

Grab a burger at Trackside Grill on your way in or out of town. Downtown Ashland is both pedestrian-friendly and cyclist-friendly, so you may consider bringing your bikes along for the trip.