After leaving the small town I grew in, I realized how much I missed Virginia’s small communities. I spent most of my childhood near the Blue Ridge Mountains and was hours from major East Coast cities. It took me several years to fully appreciate the charms of Virginia’s small towns. I was able to see the beauty of a main street with shops owned by locals, the pleasure of being in a place where you know everyone, and how appealing it is to live somewhere with access to the great outdoors. But after nearly a ten-year absence, Virginia I was drawn back into a world filled with rolling hills and four distinct seasons. There is also a love of music, history and old-fashioned comfort foods.
I may have a strong affinity for the mountain towns As a travel writer and a native Virginian, I can say that the Commonwealth is filled with dozens of incredible small towns to add to your list of places to visit. Some are better than others. In my experience as both a travel journalist and a Virginian native, the Commonwealth contains dozens upon dozens incredible small towns. However, some are more impressive than others.
So without further ado, here are the best small towns in Virginia—from a quaint getaway in the heart of horse country to a remote escape on the Eastern Shore.
Middleburg
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Middleburg Virginia is home to a number of powerhouse destinations, even if they are small. The town, also known as “the horse and hunt capital” of the United States, is so rich in history, culture and architecture that you can’t drive or walk by without taking a photo. Washington Street is lined with brick sidewalks and stone buildings that could be in a Hallmark film. Middleburg is a charming weekend getaway with many first-rate accommodation options. The stately Red Fox Inn & TavernThe city’s oldest building, dating back to 1728 is located in the center of town. Salamander Middleburg You can also find out more about the following: Goodstone Inn & Restaurant You are only a short distance away.
Lexington
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Lexington The city of Richmond is technically a town, but when you walk through the National Register of Historic Places-listed historic downtown it’s hard to imagine this as anything other than an idyllic 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. Lexington Mercantile—Lexington is full of energy, charm, and unique experiences. Lime Kiln Theater The legendary outdoor venue, an old limestone quarry/kiln, hosts a summer-long live performance lineup.
Meadows of Dan
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Meadows of Dan This small town deserves more than just a place to stop along the Blue Ridge Parkway. You’ll first find Primland, a repeat winner in Travel + Leisure‘s World Best Awards. It is also a popular resort for golfers and hikers looking for a luxury outdoor experience. Meadows of Dan boasts one of most photographed spots in the parkway, the historic Mabry’s Mill. old-fashioned candy factory. several endearing places to grab something to eat—including Primitive Coffee Market, Jane’s Country Cafe, and Poor Farmers Market.
Bedford
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The town of Bedford Since I last called it my home, the city has evolved significantly. As a child, I never imagined that there would be a local art gallery featuring curated works by experts.Goose Creek StudioA cafe that serves lunch all day long, with tasty sandwiches and other staples.Town Kitchen & Provisions), or a boutique hotel (Hotel Fauna It is scheduled to open in the second half of this year. Bedford’s proximity to the Blue Ridge Parkway and its love of history haven’t changed.
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 pie and local jam. Enjoy an afternoon of learning about World War II. National D-Day MemorialThe Loop, a pedestrian-only three-mile sidewalk with scenic views for walkers.
Cape Charles
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There are two small towns on the Eastern Shore that I recommend—the first is Cape Charles. Cape Charles is a multifaceted town that offers more than just water views and seafood. Cape Charles Beach is a great place to spend a day. You can also explore the freshwater wetlands, maritime dune woods, and wetlands at Cape Charles Natural Area Preserve. Peach Street Books, Gull Hummock Gourmet Market. Moonrise Jewelry. You can’t have an Eastern Shore trip and not have oysters. Don’t forget to eat them at least once. The Shanty.
Chincoteague
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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. There is no better place to fish or spend time on the water. You can spend your vacation reading on the beach or going shelling. The annual shelling festival is in late July. Pony Penning In 2025, the tradition will celebrate its 100th anniversary. This event attracts locals as well as tourists to the region, as Virginia’s wild pony herd is moved from Assateague Island and Chincoteague Island. Pony Swim is a popular event, in which the ponies swim six-minutes across Assateague Channel.
Floyd
Floyd is a small town in Virginia where creativity plays an important role. The mountain town, located on the Blue Ridge Plateau in Virginia, is one of the most popular stops along the heritage music trail known as The Crooked Road. Bluegrass music is played at the weekly bluegrass festival, which attracts people from all over. Friday Night Jamboree Floyd Country Store or Attend FloydFest, a multiday music festival in July. Floyd is also worth a visit for other reasons. Buffalo Mountain Ziplines, which claims to have Virginia’s highest and longest zip line, and plenty of local bites—follow the Floyd Farm Trail Find out about the best local farms, farm stores, and more.
Abingdon
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It’s not necessary to visit the largest cities of Virginia to find a diverse dining scene. One of the most interesting places is a small village in the southwest of the state. Come hungry to Abingdon where there are more than just a few local favorites. Inside The TavernThe team offers European-inspired cuisine with a Southern flair. Enjoy fried oyster tacos or cheeseburger eggrolls at Jack’s 128 PecanFill up with tonkatsu ramen at Foresta, or get your caffeine fix at The Girl & The Raven.
Wytheville
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Wytheville is a small, historic town that has many claims to fame. The town is not only famous for its historic buildings, but also for its many attractions. one of the smallest churches in the U.S., The 100-foot lookout tower at the top of the mountain offers panoramic views. Big Walker LookoutWytheville is home to a 100 year-old diner that serves hot dogs famous around the world. Skeeter’s World Famous Hot DogsOne of the most popular motorcycle trails in Virginia is located here. The Claw of the Dragon.
Woodstock
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In small towns, you’ll find some of Virginia’s best antique shops, breweries and vineyards, restaurants, farmer’s markets, scenic views, and breweries. Woodstock, Virginia is a great example. The Shenandoah valley’s historic town is perfect for a long-weekend getaway. Explore the town Spring Hollow AntiquesSip wine Muse Vineyards Beer at Woodstock BrewhouseHave a bite at Woodstock Garden CafeBrowse local produce South Street Barn Market (open all year on Saturdays). Explore the nearby area for more adventurous travelers. Seven Bends State Park You can hike to the top of the mountain Woodstock Tower.
