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The 16 Most Charming Small Towns in Virginia

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The nation’s capital is great and all, but if you’re looking for a low-key vacation that serves up breathtaking natural beauty, rich history and dreamy Southern hospitality, look no further than the neighboring state. Don’t believe us? Check out our roundup of the most charming small towns in Virginia and you’ll be more than ready to pack your bags and spend some time in the Old Dominion.

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1. Woodstock

Woodstock, Virginia was never home to the famous music festival…but it is rich in history and charm, nevertheless. In fact, this gem, situated in the heart of the beautiful Shenandoah Valley region, is the fourth oldest town in the state. Stroll the downtown district and admire the well-preserved colonial architecture, including a courthouse designed by Thomas Jefferson himself, and be sure to pop into the gourmet food stores, antique shops and boutiques that line the streets. Plus, some of the state’s finest breweries and vineyards are just on the outskirts of town, and Seven Bends State Park—an idyllic place to spend a day hiking and swimming in the lake—is just a stone’s throw away.

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2. Cape Charles

Located on the Chesapeake Bay, Cape Charles is the Virginia town to visit if you’re looking for a coastal vacation. No matter where you stay in this charming, Victorian-era community, you won’t be far from a public entrance to the pristine bayside beaches. Cape Charles is also on the National Register of Historic Places, and you’d be hard-pressed to find a higher concentration of turn-of-the-century architecture on the East Coast. This small town isn’t frozen in time, though; on the contrary, it’s a lively spot with numerous boutiques, art galleries, breweries and restaurants to explore.

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3. Abingdon

Nestled at the foot of the Blue Ridge Mountains, Abingdon is a paradise for outdoorsy types. Hiking and camping opportunities abound at the nearby Grayson Highlands State Park and the famous Virginia Creeper Trail—a scenic spot for jogging, biking and horseback riding— begins right in Abingdon’s town center. Plus, when you need a break from outdoor sporting activities, you can always take a peaceful stroll through the gorgeous 20-block historic district, or soak up the artsy vibes while sipping a glass of local wine at one of the many restaurants downtown.

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4. Middleburg

Known as the nation’s horse and hunt capital, this Loudon County destination has a population of approximately 800 people. In other words, if Southern small town charm is what you’re seeking, Middleburg won’t disappoint. Of course, equestrian activities are on offer, but if you don’t feel like hitting the polo fields, you can always head to the National Sporting Library & Museum to learn about the town’s rich history, or tour the historic Aldie Gristmill for a taste of the region’s industrial heritage. It’s also worth noting that the picturesque Middleburg countryside is home to some of the state’s finest wineries, so you can get a taste of some quality vino during your visit, too.

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5. Chincoteague

Here, a small port town on Virginia’s Eastern shore with major appeal. For starters, there’s Chincoteague National Wildlife Refuge, which boasts unspoiled beaches, hiking trails and, most famously, lots of wild ponies. (Psst: Visit in the summer for the annual Pony Swim, and you can see the memorable event first-hand, whilst enjoying a full-week of festivities, too.) Finally, given its location on the Eastern Seaboard, it should come as no surprise that you can find an abundance of swoon-worthy and oh-so fresh seafood at any of the numerous gourmet restaurants in town.

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6. Warrenton

Another destination for all things equestrian, Warrenton is a Fauquier County town that’s commonly referred to as ‘horse country,’ and was even home to Virginia’s first Gold Cup Race back in 1922. Historic sites to visit include the famous 1959 statue of Chief Justice John Marshall at the old courthouse, as well as the Fauquier Museum of History, which is located in the former home of a Confederate military commander. You can also soak up more history with a visit to one of the nearby Civil War battlefields, or simply enjoy the natural splendor of the area by exploring the many mountain trails and caves just outside of town.

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7. Damascus

Damascus has earned its nickname as “Trail Town, USA,” due to its prime location at the intersection of the Virginia Creeper Trail and Appalachian Trail. This quaint town also provides easy access to Mount Rogers National Park, which is home to the (namesake) tallest summit in the state. Needless to say, there is no shortage of outdoor recreation activities in and around Damascus—and the hiking trails serve up plenty of breathtaking natural beauty, to boot. If you’re looking for a serene escape from city life, Damascus surely fits the bill.

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8. Farmville

Folks who are looking for family-friendly outdoor adventure might consider paying a visit to Farmville—a little bijou on the banks of the Appomattox River that boasts hip college town vibes and lots of Southern charm. Home to Longwood University, the town itself is small, but bustling and vibrant. Aside from its desirable ambience, Farmville also offers visitors easy access to the High Bridge Trail—a winding trail that begins in the center of Farmville and finishes with a hike over a stunning historic bridge that hovers 125 feet above the Appomattox River. (And, yes, the views are spectacular…assuming you aren’t too afraid of heights to stomach it, that is.)

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9. Lexington

Despite its modest size, Lexington has a slightly more metropolitan feel than some of the other small towns on our list. Most notably, this Virginia destination boasts cultural attractions galore—including a variety of historic sites (like Lee Chapel and the Stonewall Jackson House), as well as museums, art galleries and performance venues. If you’re paying a visit to Lexington, be sure to snag a table at one of the many top-rated restaurants while you’re in town.

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10. Smithfield

Smithfield has a character all of its own: low-key vibes, authentic Southern hospitality and a sleepy feel that belies the vibrant cultural attractions on offer. For starters, Smithfield is the birthplace of Virginia ham—a delicacy that’s best enjoyed with peanuts at a local eatery. Wharf Hill, the Mansion on Main, and St. Luke’s church are a few of the major historical sites you should visit…but mostly, Smithfield is a place you go to sit on the porch and smell the bacon.

11. Onancock

This welcoming harbor town on the Eastern Shore boasts a walkable waterfront and marine activities aplenty, including kayaking, boat tours, and access to the Tangier Island Ferry—a time machine that transports you to a remote Chesapeake Bay Island where the natives still speak a Restoration-era dialect. If you prefer to stay on solid ground, you can always explore the scenic nature trail runs along the Onancock creek, or treat yourself to a meal at an award-winning restaurant followed by a show, be it a first-run film at Roseland Theater or a live performance at the North Street Playhouse. In other words, this unique and charming spot has a little bit of everything on offer.

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12. Culpeper

Here’s another quirky town with something for everyone: History buffs will have a field day, so to speak, at Culpeper’s several well-preserved Civil War battlefields, gourmands will appreciate the top-notch farm to fork fare served up at the local restaurants, and everyone in your travel party is sure to find a treasure at one of the town’s boutiques and antique stores. It’s also worth noting that this up-and-coming town is just an hour and a half from Washington D.C., and you’d be hard-pressed to find a better place to take a break from the hubbub of the capital city.

13. Kilmarnock

Kilmarnock, which belongs to Virginia’s River Realm in the Northern Neck of the state, is known for having a friendly small-town atmosphere, but with more urban amenities than most. Tour one of the town’s museums, like the Kilmarnock Museum or Steam Boat Museum, or enjoy a day outdoors on the Baylor Park Nature Trail—a prime and oh-so pretty spot for birding and wildlife watching.

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14. Manassas

Manassas has a significant Civil War past, which visitors can get a taste of by taking a stroll through the Old Town Historic District or spending a day at the Manassas Museum—an institution dedicated to the town’s rich history. That said, there’s modern flair to be found here, too. In fact, charming mom-and-pop shops, lively restaurants and art galleries can be found on nearly every storybook street in town.

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15. Staunton

Exquisite Victorian homes, swoon-worthy restaurants, independent stores and cozy cafes line the streets of Staunton—a cultural hub in the Shenandoah Valley that’s prized for its vibrant music and arts scene, which includes the American Shakespeare Center and Heifetz International Music Institute. Beyond that, Staunton’s location between the Allegheny and Blue Ridge Mountains makes it an ideal home base for anyone looking to spend some time in the Great Outdoors.

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16. Occoquan

Sitting pretty on the banks of the Occoquan River, this picturesque town is paradise for foodies and shopaholics alike. Indeed, there are more than 60 boutiques, restaurants and gourmet food stores to explore. If you’re hungry for more, you’ll be pleased to know that Occoquan is located just 23 miles outside of Washington D.C.—but we suspect the town’s inviting, laid-back vibe will be enough to make you want to stay put.