10 Most Charming Towns to Visit in Virginia

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Virginia isn’t only for lovers, it’s for history lovers, beach lovers, and more, with a wealth of beautiful destinations that are well worth a visit. There are so many options in this diverse state, from small coastal towns to those with mountain beauty. Discover your next getaway spot at one of these top charming towns to visit in Virginia.

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Fredericksburg
Fredericksburg, VA skyline

Fredericksburg

A popular weekend getaway in Virginia, Fredericksburg is filled with charms and a rich history as the home to a number of significant battles in the Revolutionary and Civil Wars. Step in, and you’ll feel like you’ve been transported back in time, with its tranquil neighborhoods lined with historic homes and other structures that house a surprising variety of interesting shops and outstanding restaurants. The Historic District contains over 350 buildings dating back to the 18th and 19th centuries. Plus, there are more than 15,000 Union burials at the Fredericksburg National Cemetery and preserved portions of Civil War battlefields.

Abingdon
Whites Mill, Abingdon

Abingdon

Abingdon is surrounded by the picturesque Blue Ridge Mountains, making it an ideal destination for those who want to enjoy outdoor adventures and more. You can walk, bike, jog or hop on a horse on the Virginia Creeper Trail which begins right downtown, while the historic downtown district is perfect for a stroll with its cobblestone sidewalks. After a day of play, indulge in a relaxing treatment at the Martha Hotel & Spa or catch a play at the famous Barter Theatre. Wolf Hills Brewing Co. offers outstanding craft-brewed beers and often hosts live music to go along with it.

Chincoteague
Chincoteague, Virginia

Chincoteague

The town of Chincoteague became famous after Marguerite Henry’s children’s book Misty of Chincoteague was made into a film in 1961. The story focuses on the Chincoteague wild ponies located on neighboring Assateague Island, where they’ve lived for hundreds of years. The ponies wander the beaches, the marsh, and the islands, munching the dune and marsh grasses. Every year, the Chincoteague Volunteer Fire Company brings a herd of 150 ponies from Assateague Island to Chincoteague Island. Known as “the swim,” it brings thousands of spectators to watch them. You’ll also find lots of cozy hotels, a variety of outstanding eateries, and the Chincoteague National Wildlife Refuge, which covers more than 14,000 acres of beach, dunes, marsh, and maritime forest. The entire island is a sanctuary, offering practically endless opportunities for outdoor activities.

Middleburg
The Red Fox Inn & Tavern in Middleburg, Virginia

Middleburg

Middleburg, located in Loudoun County, is one of the best small towns in Virginia. Although it only takes up six blocks and has a population of less than 1,000, it’s loaded with history and surrounded by some of the most impressive horse countries you’ll find anywhere in the nation. The Middleburg Historic District is made up of many magnificently preserved 18th and 19th-century buildings. Listed on the National Register of Historic Places, it includes the Red Fox Inn, which opened in 1728 as a stopping point for travelers. The inn is the town’s most famous landmark and is actually older than Middleburg itself, which was founded in 1787. If you’re a wine enthusiast, Middleburg also makes a great base for exploring the multiple wineries in the surrounding area.

Staunton
Beverly Street, in downtown Staunton, Virginia

Staunton

Some say Staunton is Virginia’s best-kept secret. Settled in 1732, it was once the state capital and is also home to the birthplace of President Woodrow Wilson. Built in 1846, it sits atop the historic Gospel Hill. Visitors can take a self-guided tour through seven galleries that outline Wilson’s early years through the First World War. The town also hosts the American Shakespeare Center, the world’s only authentic replica of the Blackfriars Theater, and it has its own living museum, the Frontier Culture Museum of Virginia, which tells the tales of thousands of colonial immigrants who migrated to America. Thanks to city planners who were careful not to interrupt the views in the historic districts with power lines and the like, Staunton has done an excellent job at retaining its appeal from days past. You’ll find countless Victorian homes to admire up and down the streets – be sure to take time to marvel at the impressive Trinity Church with its Tiffany window.

Lexington
Lexington, Virginia

Lexington

Lexington has an exceptional concentration of historic sites and museums for the history buff with its strong connections to military history and the Civil War. You’re sure to appreciate the many music venues, theaters, art galleries, and restaurants – Lexington also boasts a number of highly-rated farm-to-table eateries.

Culpeper
Culpeper, Virginia

Culpeper

Culpeper is dotted with Victorian and Colonial homes, art galleries and antique shops, retailers selling one-of-a-kind items and handcrafted goods, world-class restaurants, and classic diners. Its Main Street is even home to some fantastic wineries and the only legal moonshine distillery in the state, Belmont Farm Distillery. Explore the town’s rich history from prehistoric times through today, including the founding of the nation, at the Museum of Culpeper History, and walk in the footsteps of soldiers who lived and died here during the bloody battles of the Civil War at the Graffiti House at Brandy Station, Cedar Mountain Battlefield, and Kelly’s Ford.

Smithfield
Wentworth-Grinnan House, Smithfield

Smithfield

Named one of “America’s Happiest Seaside Towns” by Coastal Living in 2015, Smithfield oozes small-town Southern charm. It was founded on the Pagan River near Jamestown and boasts a long history as part of the Virginia Colony dating back to 1634. It’s famous for its hams as the world’s largest pork processor, so you can expect to see lots of it on the menu at area restaurants and the frequent community BBQs. Cultural attractions include the Isle of Wight Museum, Historic Fort Huger, The Old Courthouse of 1750, and Fort Boykin Historic Park. Take a walk through the pretty historical downtown to check out historic homes and the grand Smithfield Inn.

Warrenton
Warrenton, VA

Warrenton

Named for Revolutionary War hero General Joseph Warren, this Fauquier County town was incorporated in 1810 and offers an interesting mix of old and new, historical and urban. The courthouse and old jailhouse, which was part of Warrenton during its earliest years, have been impeccably preserved and now serve as museums that house Civil War exhibits, jail cells, and Native American artifacts. Buildings, many from the 19th century, remain the same as they were when they were first constructed, however, their original purpose has been changed so that they now house galleries, boutiques, and specialty shops.

Occoquan
Occoquan

Occoquan

Occoquan was the home of the first automated grist mill in the entire country. Named one of Virginia’s top small cities by CitiesJournal, it sits along the banks of the Occoquan River. This small riverside town has a population of under 1,000, but it’s big when it comes to charms. Founded in 1765 with the construction of tobacco warehouses and grist mills, today Occoquan is considered an artists’ community and offers lots of delights, like ghost walks, boating and fishing, and more than 100 shops and restaurants. You’ll even find a Scandinavian spa and a tea room – the Pink Bicycle Tea Room isn’t the stuffy type, kids and tea lovers alike enjoy visiting here. If you want to enjoy a fun night out, head to the Cock & Bowl where you can dine on European fare, sip Belgium brews, and listen to live music.

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