10 Best Small Towns in Virginia

Middleburg

Middleburg is a powerhouse destination in Virginia, albeit a small one. Known as the “horse and hunt capital of the nation,” the town is filled with history, culture, and architecture you simply can’t walk or drive past without snapping a picture. The main thoroughfare, Washington Street, is lined with stone buildings, brick sidewalks, and businesses that look as if they could star in a Hallmark movie. There are also quite a few first-rate accommodations in Middleburg, making it an extra-charming weekend retreat. The stately Red Fox Inn & Tavern, which has roots dating back to 1728, sits prominently in the middle of town, and both Salamander Middleburg and Goodstone Inn & Restaurant are just a short drive away.

Lexington

Lexington might technically be categorized as a city, but as soon as you enter the historic downtown, an area listed on the National Register of Historic Places, it’s difficult to describe this part of Virginia as anything other than a picturesque small town. Home to Washington and Lee University and Virginia Military Institute (VMI) plus a roster of local businesses you can navigate to via antique brick sidewalks—I love Lex Running Shop, Purveyors on Main, and Lexington Mercantile—Lexington is full of energy, charm, and unique experiences. Lime Kiln Theater combines all three of those characteristics, offering an annual summer lineup of live performances from its legendary outdoor venue (an old limestone quarry and kiln).

Meadows of Dan

Meadows of Dan is more than just a stop on the Blue Ridge Parkway; it’s a small town that deserves a hefty dose of recognition. For starters, this is where you’ll find Primland, a repeat winner in Travel + Leisure‘s World’s Best Awards and a favorite resort among golfers, hikers, and travelers searching for a luxe outdoor experience. Meadows of Dan also lays claim to one of the most photographed spots on the parkway (the historic Mabry Mill), an old-fashioned candy factory, and several endearing places to grab something to eat—including Primitive Coffee Market, Jane’s Country Cafe, and Poor Farmers Market.

Bedford

The town of Bedford has significantly evolved since I last called it home. When I was younger, I couldn’t have imagined there would be an art gallery with an expertly curated selection of local work (Goose Creek Studio), an all-day cafe with a flavorful menu of sandwiches and other lunch staples (Town Kitchen & Provisions), or a boutique hotel (Hotel Fauna is set to open later this year). What hasn’t changed, though, is Bedford’s incredible proximity to the Blue Ridge Parkway, its admiration of history, or its walkability.

Before heading up to hike one of three peaks that make up the Peaks of Otter—Flat Top, Sharp Top, and Harkening Hill—pop into Mountain Fruit & Produce for apple fried pies and local jam. Spend an afternoon learning World War II history at the National D-Day Memorial, then venture back to town to get your steps in around “The Loop,” a three-mile pedestrian sidewalk that provides walkers with a nice stretch of scenic views.

Cape Charles

There are two small towns on the Eastern Shore that I recommend—the first is Cape Charles. You may initially be drawn to this part of the state for water views and fresh seafood, but Cape Charles will quickly demonstrate its appeal is multifaceted. Spend a day at Cape Charles Beach, explore freshwater wetlands and a maritime dune woodland at Cape Charles Natural Area Preserve, and get some shopping in at Peach Street Books, Gull Hummock Gourmet Market, and Moonrise Jewelry. Of course, it wouldn’t be a true Eastern Shore trip without oysters, so try not to leave without having dinner at The Shanty.

Chincoteague

Another Eastern Shore favorite, Chincoteague is the type of small town where you could easily spend a week—if not longer—and never grow bored. If you love to get out on the water and fish, you won’t find a better place to spend your time. If you prefer to read on the beach, take long sandy walks, or go shelling, it’s your dream vacation destination. You can also time your visit for late July, when the annual Pony Penning occurs; 2025 marks year 100 for the tradition. The event brings locals and tourists to the area as Virginia’s herd of wild ponies is moved from Assateague Island to Chincoteague Island. It includes the famous Pony Swim, where the animals swim the six-minute journey across the Assateague Channel.

Floyd

Creativity plays a defining role in the culture of many small towns in Virginia, and nowhere is this more apparent than in Floyd. The mountain town is located atop the Blue Ridge Plateau, and it’s one of the biggest stops along Virginia’s heritage music trail, also known as The Crooked Road. People come from far and wide to listen to bluegrass music at the weekly Friday Night Jamboree at Floyd Country Store or attend FloydFest, a multiday music festival in July. Other reasons to plan a visit to Floyd include Buffalo Mountain Ziplines, which claims to have Virginia’s highest and longest zip line, and plenty of local bites—follow the Floyd Farm Trail to discover some of the best local farms and farm stores.

Abingdon

You don’t need to travel to Virginia’s biggest cities to experience a diverse culinary scene; one of the most impressive dining destinations is a small town tucked in the southwest corner of the state. You’ll want to come hungry to Abingdon, where the food offerings extend beyond a couple of local favorites. Inside The Tavern, housed in Abingdon’s oldest building, the team serves up European-inspired entrees, all whipped up with a Southern touch. Dine on cheeseburger egg rolls or fried oyster tacos at Jack’s 128 Pecan, fill up with tonkatsu ramen at Foresta, or get your caffeine fix at The Girl & The Raven.

Wytheville

If you’re road tripping along I-81, schedule in some time to stop in Wytheville, a small town with several claims to fame. Not only does it have one of the smallest churches in the U.S., a water tower painted to resemble a rainbow-striped hot air balloon, and a 100-foot-tall lookout tower with panoramic views (found at Big Walker Lookout), but Wytheville also has a 100-year-old diner with famous hot dogs, Skeeter’s World Famous Hot Dogs, and one of the most well-known motorcycle trails in this part of Virginia, The Claw of the Dragon.

Woodstock

Some of Virginia’s best antique stores, breweries, vineyards, restaurants, farmers markets, and scenic views are hidden away in small towns across the state. Case in point: Woodstock, Virginia. This historic town in the Shenandoah Valley is ideal for a long weekend. Poke around Spring Hollow Antiques, sip wine at Muse Vineyards or beer at Woodstock Brewhouse, have a bite to eat at Woodstock Garden Cafe, and peruse the local produce at South Street Barn Market (open year-round on Saturdays). More adventurous travelers should also make a point to explore nearby Seven Bends State Park or hike up to the Woodstock Tower.