Updated April 2025 by Heather Bien
The Commonwealth of Virginia is home to picturesque pockets of countryside and small-town charm. From posh wineries and boutique hotels to bucket-list adventures and historic sites, there’s something for every type of traveler within these six small towns in Virginia. Take a look!
Middleburg, VA
The “Horse and Hunt” Capital of the Country
Middleburg will plop you into a Jane Austen scene in the English countryside. Picturesque landscapes, low stone walls, and stately horse farms are standouts of this town just an hour from D.C. in wine-famous Loudon County.
The settlement was established in 1728 as a fieldstone tavern on an old Native American trail by a cousin of George Washington. That tavern became the Red Fox Inn, which is still the heart of Middleburg today. At the turn of the 19th and 20th centuries, the town became a popular destination for fox hunting and steeplechasing, earning it a reputation as the “Nation’s Horse and Hunt Capital.”
The historic downtown is lined with chic boutiques, dapper men’s stores filled with tartan plaid and leather-clad riding gear, and cuisine that spans from fireside tavern fare to farm-to-table gourmet. Posh lodgings are sprinkled all over Middleburg.
You can’t go wrong with a room at the historic Red Fox Inn, the five-star Salamander Resort, or the elegant Goodstone Inn & Restaurant, which has been named one of America’s best restaurants (and best wine restaurants). Salamander’s Harrimans Virginia Piedmont Grill garners rave reviews for its flavorful, locally inspired dishes, while Hunters Head Tavern and Red Fox Inn’s restaurant serve fresh takes on traditional tavern fare. Try Common Grounds for delicious espresso and bagel sandwiches.
The National Sporting Library & Museum has a trove of fine art, books, and exhibits about Middleburg’s heritage and the tradition of country pursuits like angling, steeplechasing, fox hunting, flat racing, polo, and more. Nearby mountains create a scenic backdrop and an ideal grape-growing climate. Twenty wineries are within half an hour’s drive, like local favorites Greenhill Vineyards and Boxwood Estate Winery.
Whether you’re looking for a luxe spa retreat, a fun vineyard day, or a taste of equestrian life, Middleburg’s got it!
Lexington, VA
Civil War History Meets College-Town Cool
This gem of a small town is tucked away in the Shenandoah Valley but close enough to I-81 to make it accessible from many big cities. It’s got a rich history, two colleges (Washington & Lee and Virginia Military Institute), and outdoor scenery galore. The two institutions have created an ever-growing demand for boutique hotels, wine bars, and trendy shops.
With only a few stoplights, you can explore downtown and both campuses easily on foot. Once you’ve hit the in-town sites like W&L’s University Chapel & Galleries and the VMI Museum, there is more to see nearby.
Stay at The Georges, a thoughtfully restored, 200-year-old inn ranked #4 Best City Hotel in America in the 2021 Travel + Leisure World’s Best Awards. In the morning, locals grab their own mug off the wall at Lexington Coffee Shop and head for the serve-yourself station of delicious, locally roasted brew.
Just down the road, Pure Eats makes fresh donuts and bagels for an easy breakfast. This is no better Lexington lunch than Blue Sky, and waiting in the inevitable queue is worth it. People flock to this family-run corner eatery for homemade focaccia, soups, and sandwiches.
Bistro On Main and Southern Inn are cozy, old-school staples for supper, or you can enjoy the creative fare at The Red Hen or Haywood’s. Grab a fireside nightcap in the TAPS living room or a local brew at the super-cool Heliotrope Brewery.
Outdoor wanderers shouldn’t miss the Chessie Nature Trail, a flat, six-mile trail along an old rail bed, and the Maury River, running from Lexington all the way to Buena Vista. For a more challenging trek with incredible views, head up House Mountain, or tube down Goshen Pass. Just miles down the road is Natural Bridge State Park, one of the nation’s top natural wonders. Whether or not you’re traveling with kids, Boxerwood Nature Center & Woodland Gardens is a whimsical, off-the-beaten-path gem worth exploring.
Abingdon, VA
Outdoor Adventure Meets On-Stage Culture
Close to the Tennessee border is the eclectic little town of Abingdon. Known as a respite for many Appalachian Trail hikers, it’s filled with funky, hospitable people and businesses. Book a room at a quaint bed and breakfast — like Black Fort’s Inn — or opt for the stately four-star Martha Washington Inn & Spa (lovingly called The Martha) for a well-situated home base. It’s across the street from the famous Barter Theatre, the longest-running professional Equity theatre in the United States. No matter what’s playing, you can plan on an entertaining night.
One of the most extraordinary things about this town is its connection to the Virginia Creeper Trail. Pick one of these bike shops in town to rent your bikes and get shuttled to the top of the 35-mile-long trail. It’s almost all downhill from there. This famous bike trail meanders down an old rail bed that hugs rivers and streams and crosses the Appalachian Trail a few times. Dotted with a few chances to refuel with snacks and ice cream, you’ll work up a great appetite for the rest of your Abingdon weekend.
If The Tavern is Abingdon’s oldest and most famous restaurant, Foresta is its modern, eclectic new counterpart serving up elevated Italian and Asian fusion dishes, and 128 Pecan is a no-frills farm-to-table option. Grab a cocktail at Rain, or order a cup of coffee at Wolf Hills Coffee as you walk through the Abingdon Farmers’ Market.
Hot Springs, VA
A Draw for Three Centuries of Travelers
Have you ever wondered where you can find the oldest resort in America? Hot Springs, VA, is the place. The Omni Homestead Resort was founded in 1766 — before the United States was even a nation. For three centuries, travelers have come from near and far to take to the hot springs that naturally bubble up from the earth in this mountain town.
The Warm Springs Pools, which have boasted fans including Thomas Jefferson, maintain their original historic architecture but have been completely renovated into stunning and relaxing modern bathhouses.
Whether you want to escape the summer heat or discover a cozy winter getaway, Hot Springs is one of Virginia’s most idyllic small towns. Hidden away in the lush mountains of Bath County, this is where you’ll find outdoor adventures, like kayaking the Jackson River or hiking the Hidden Valley Trail.
The primary focus of a Hot Springs weekend is relaxation, but you can also sprinkle in culture with a trip to the Warm Springs Gallery or a stop at the Garth Newel Music Center. Pop downtown for a tasting of Virginia wine at Rock Roadhouse Winery’s tasting room.
The Homestead has a range of restaurants, but if you want to go into town, the Milk House Market is a favorite stop for lunch, while the Waterwheel Restaurant at the Inn at Gristmill Square combines fine dining with a historic setting.
Irvington, VA
Waterfront Charm Meets Virginia’s Oyster Culture
The Northern Neck is one of the most storied regions in Virginia, and thanks to The Tides Inn, the tiny town of Irvington has made a name for itself. This waterfront hotel underwent a massive renovation in recent years. While it already had a dedicated fan base of generations of families who return year after year, it’s now a destination for those new to exploring the region.
From oyster excursions to sunset happy hours to a bike ride into town, this is the ultimate coastal getaway.
While Irvington may be small, it’s packed with shops and restaurants. Grab breakfast at The Local, happy hour at 77Social, and dinner at Dredge. Stroll down the main drag to check out storefronts, including Irvington Home Goods, Dear Neighbor, and Objects Art and More. Want a splurge-worthy dinner? Sit down for a Chesapeake Bay-inspired meal at Salt & Meadow at the Tides.
If you’re in town from May through October, don’t miss the Irvington Farmers’ Market, which features vendors and artisans from across the region.
Once you’ve bopped around Irvington, head over to nearby White Stone for shopping at Pink Lemon and Pointe Provisions. Snag some baked goods from Out of the Oven Bakery and dinner at Adrift, where the menu changes regularly.
Cape Charles, VA
A Beach Town with a Quaint Historic District and Calm Waters
If you’re used to beach towns with crowded boardwalks and sky-high hotels, throw all those visions out the window. Cape Charles is a small town on Virginia’s Eastern Shore that’s as charming as it gets. With a quaint historic district and swoon-worthy Victorian architecture, this beachfront village is more relaxing than rowdy.
From Peach Street Books to Brown Dog Ice Cream, there are darling spots around every corner. Check out Deadrise Italian for delicious pizza, Mason Avenue Bakery for fresh croissants, or Cape Charles Distillery for something a little stronger.
Of course, the main reason to head to Cape Charles is the stunning landscapes. The water is famously calm here, making it the perfect getaway if you’re traveling with children. You can also explore over 560 acres of beachfront nature and coastal habitats at Kiptopeke State Park.
While vacation rentals are available throughout Cape Charles, don’t forget to look into bed and breakfast options, like the Fig Street Inn or the Bay Haven Inn.
One thing you can expect around every corner in Abingdon, Lexington, Middleburg, Hot Springs, Irvington, and Cape Charles is friendly locals ready to help you discover why they love their towns. Go see why small-town Virginia truly is for lovers!
This article contains hotel affiliate links. We may receive a commission if you make a reservation after clicking on one of these links.
**********
Keep up with all of the amazing things going on around the South. Subscribe to StyleBlueprint!
