Virginia attracts millions of visitors every year with its beautiful national parks, its phenomenal museums, and its historic monuments and landmarks. However, on top of the big names – namely Richmond, Arlington, and Norfolk – Virginia also has some exceptionally picturesque and charming towns that need added to your travel list.
Damascus, Washington County
Love the outdoors? Pack up your gear and hit the road for Damascus! The Virginia Creeper Trail (see in pic), full of hiking opportunities like the Appalachian, Iron Mountain, and Appalachian Trails, will make you give it another moniker - “Trail Town USA”. If you’re working on burning fuel, just visit one of the restaurants at the Old Mill Inn in town; they serve delicious casual grub and offer locally brewed beers and live tunes from the folks down at Damascus Brewery.
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Bedford, Bedford County

Nestled between the Blue Ridge Mountains and Piedmont plateau is Bedford, town visitors often overlook but is packed with traditional small-town ambiance. Definitely stop by National D-Day Memorial, a poignant tribute to the Allied soldiers who fought and died in that significant World War II campaign, as well as the Bedford Boys Tribute Center to browse their belongings. Bedford’s quaint Main Street also makes a wonderful setting for a casual shopping spree.
Farmville, Prince Edward and Cumberland Counties
In the heart of Virginia on the border of Prince Edward and Cumberland counties is Farmville, one of the great college towns on my road trip, full of both historic sights and outdoor activities. Longwood University and Hampden-Sydney College mean the area gets a strong college vibe. Another natural highlight of Farmville is the High Bridge (pictured) soaring 125 feet above the Appomattox River and a favorite for hikers and bikers. And don't skip the awesome local museum that chronicles the 1951 Moton school strike, the start of an influential civil rights demonstration that happened right in town.
Onancock, Accomack County
A laid-back harborside enclave, the town conveniently locates itself in relation to Chesapeake Bay, and it's no surprise that people enjoy kayaking, sailing, and fishing here. But the town's charms don't stop there. An excellent arts scene features miniature galleries, boutique stores brimming with handcrafted products... And a tiny independent picture house named the Roseland Theatre which usually pla.
South Boston, Halifax County
Ideal for those looking for a quiet South Boston base for exploring southern Virginia, South Boston offers all of this and more. South Boston Speedway, a small and fast-running racetrack, caters well to sports enthusiasts with regular NASCAR meetings staged there. The Main Street in South Boston is a pleasant mix of local independents and a great array of diners, restaurants, pizzerias and more!
Norton, Wise County
Though it is possibly the smallest incorporated city in the Commonwealth of Virginia, that only means there's more opportunity to get to know Norton and all its inviting attractions. Between beauty spots including Flag Rock Recreation Area and the Upper Norton Reservoir, family activities at the local cinema and bowling alley, and a variety of dining choices including Mexican dishes, pizza, and traditional American cuisine, you're sure to be satisfied.
Coeburn, Wise County

Tucked away in Virginia's southwestern Appalachian Mountains, Coeburn serves as an ideal place for getting back to nature. Take the short walk along the beautiful Little Stony National Recreation Trail where you can find falls called the Little Stony Falls. Close by, you will also discover the amazing High Knob Recreation Area, which has one of the highest campsites in the region. For an adrenaline-fueled afternoon, visit a local track that hosts its own fun variety of weekend auto racing.
Cape Charles, Northampton County
Whether you want a dreamy beach town with some flair or are just looking to slow down and relax, Cape Charles is it! This waterfront city, located in the state of Virginia’s eastern shore, has a charming fishing pier made of wood. You’ll find late-century historic architecture within the quaint historic district, and clear, calm waves will lead to pristine sandy beaches. Enjoy watersports, hiking, or boating during your time at the beach, or check out Cape Charles on land where you can meander through local boutiques for artisan wares or tour historic homes.
Warrenton, Fauquier County
This building is the third courthouse and dates to the 19th Century, an original from 1795 that stood there previously. Along with the other numerous and beautiful buildings in the Old Town of Warrenton, such as the old Jailhouse and a Presbyterian church used as a Civil War hospital, it creates a perfect location for a weekend escape. A long-standing farmer's market exists along with some really great pub restaurants to really top off a trip here.
Final Thoughts
While Virginia's major cities hold plenty of appeal, the heart of the Commonwealth lies within its small towns. From the mountain trails of Damascus and Coeburn to the quiet waters of Cape Charles, these destinations offer rich local history, great food, and easy access to nature.
Whether you are planning a weekend road trip or looking for a quiet coastal escape, taking time to visit these spots gives you a true look at Virginia's local character.
Frequently Asked Questions
What is the best town in Virginia for outdoor activities?
Damascus is often considered one of the best spots for outdoor enthusiasts. Known as "Trail Town USA," it serves as a central hub for major routes like the Virginia Creeper Trail, the Appalachian Trail, and the Iron Mountain Trail.
Which small towns in Virginia are great for a coastal or waterfront trip?
Cape Charles and Onancock are top choices on Virginia’s Eastern Shore. Cape Charles offers sandy beaches, calm waters, and historic architecture, while Onancock is ideal for kayaking, sailing, and exploring local art galleries along the Chesapeake Bay.
What historic sites can you visit in Farmville, Virginia?
Farmville features the High Bridge, a historic rail structure sitting 125 feet above the Appomattox River. The town is also home to the Robert Russa Moton Museum, which marks the site of a 1951 student strike that played a major role in the American civil rights movement.
Are these small Virginia towns suitable for a weekend getaway?
Yes. Destinations like Warrenton, Bedford, and South Boston are ideal for short trips. They offer a mix of local shops, historic walking areas, regional dining, and quick access to nearby parks and scenic drives.