Here Are 10 of the Most Beautiful, Charming Small Towns in Virginia

Virginia is known for many things: history, natural beauty, and (bless our hearts) lots of southern charm. But one of Virginia's best features is the abundance of small towns and communities throughout the state. A small town can be anything from a couple of hundred people to 10,000, and what sets it apart is the community and camaraderie you receive when you visit. These small towns in Virginia move at a slower pace. They often exude a sense of nostalgia from a time long past, where everyone knows your name, the restaurant knows your order, and you can't walk into any building without catching up with a few acquaintances. From the beautiful corners of the Southwest to the far Eastern Shore, you'll find plenty of delightful small towns where you can still get this experience.

We think it's worth mentioning that every town in Virginia is worth a visit. While we’ve provided a list of some of our favorite cities in Virginia, it’s by no means an exhaustive list. For the time being, here are a few of the most charming towns in Virginia that have garnered national and statewide praise for their community, beauty, and all-around quality of life.

1. Chincoteague

First settled in the 1700s, Chincoteague gained the spotlight in the late 1940s with the publication of "Misty of Chincoteague," a story about one of the island’s now-famous wild ponies. Today, Chincoteague (and sister island, Assateague) is best known for its Annual Pony Swim and Auction, but also offers pristine beaches, amazing seafood, boat tours, home tours, and an all-around chilled-out beach town experience.

From horseback riding to kayaking around the island, a day trip to this charming small town in Virginia is pure perfection. I'd recommend visiting Chincoteague in the summer so you can take advantage of the longer days and endless outdoor adventures.

2. Abingdon

Abingdon is nestled in the Blue Ridge Mountains of Southwest Virginia. Rich with history, this small town was once home to the Cherokee Nation and, by the mid-18th century, had been explored by the likes of William Byrd and Daniel Boone. Named after Martha Washington’s ancestral home in England, Abingdon became a town in 1778 and remains so today. Its historic downtown is home to a thriving arts and culture scene, featuring venues like the historic Barter Theatre, as well as galleries, museums, and markets.

Whether you want to take a day trip to Abingdon or spend a long weekend in this charming small town, you'll never be bored. Check out our feature piece where we highlight all of the best things to do in Abingdon for some travel inspiration.

3. Smithfield

This lovely waterfront town in Virginia, known for its world-famous ham, boasts a long history as part of the Virginia Colony dating back to 1634. Founded on the Pagan River near Jamestown, Smithfield eventually became the "Ham Capital of the World."

Today, Smithfield Foods, a Fortune 500 company, is the world’s largest pork processor and hog producer in the U.S. So, is it good food that makes this town so happy? Perhaps, but an incredible community spirit certainly helps. With concerts in the park, community BBQs, and countless other local events, this town makes the most of its stunning historical downtown featuring sites like the Smithfield Inn, as well as historic homes, schools, and churches.

When you're planning your trip to Smithfield, be sure to visit Windsor Castle Park. This 208-acre park is an awesome, family-friendly outdoor space that's done a wonderful job of blending play and nature.

4. Middleburg

There are towns, and then there are small towns such as Middleburg in Loudoun County. Although it only takes up six blocks and boasts a population under 700, this small town in Virginia is packed with history and surrounded by some of the most beautiful horse country anywhere in the nation.

The Middleburg Historic District, made up of many beautifully preserved 18th- and 19th-century buildings, is listed on the National Register of Historic Places and includes the Red Fox Inn. Considered one of the oldest continuously operating inns in the U.S., it was founded in 1728 and is Middleburg’s oldest structure. Since the early 1900s, Middleburg has been a destination for fox hunting and steeplechase events, earning it the title of "Horse and Hunt Capital of the United States." Today, the town is home to the National Sporting Library research center for horse and field sports. And, it's one of the most quaint towns in Virginia as well.

Consider staying at this unique Airbnb in Middleburg when you're planning your trip. It's just the right mix of quirky and homey. And it's a slam dunk for animal lovers.

5. Lexington

Although it’s home to two colleges, VMI and W&L, Lexington is much more than "just" a college town. Surrounded by the breathtaking beauty of the Shenandoah Valley, this quiet little haven offers charm and history in abundance.

History buffs will love the historic sites and museums at every turn. If you are more interested in shopping, we suggest exploring historic downtown, which offers an array of specialty shops, boutiques, art galleries, antiques, and more, along with a surprisingly large selection of local restaurants and cafes. Lined with historic homes and buildings, the streets of Lexington retain the beauty of days gone by, making it easy to see why this town has been recognized as one of the best small towns in Virginia.

6. Onancock

Onancock is quite possibly one of the greatest hidden gems of the Eastern Shore. In fact, Onancock was called "the Gem of the Eastern Shore" by none other than Captain John Smith himself and was founded in 1680 as Port Scarborough. With a live theater, award-winning restaurants, local artists, craftsmen, sculptors, actors, dancers, musicians, and glassblowers, there's no shortage of things to see and do in what we think is one of the most quaint towns in Virginia.

Visit former Native American villages, kayak to local wineries, and go sailing. Or just sit in a pub on the water and listen to live music. You simply can’t go wrong with Onancock when you're looking to explore cute towns in Virginia.

7. Staunton

Staunton is no stranger to praise. Founded in 1732, this lovely little town in the Shenandoah Valley offers historic architecture, culture, and a friendly down-home atmosphere that makes its place in the rankings well-deserved. Surrounded by beautiful mountains, Staunton provides culture a-plenty with sites like the American Shakespeare Center and The Frontier Culture Museum, and offers no shortage of sensational specialty shopping, dining, and nightlife opportunities. Add in a great cost of living and tons of southern charm, and you'll understand why it's one of the best small towns in Virginia.

8. Occoquan

Occoquan sits on the Occoquan River. This riverside town in Virginia may have a population of around 1,000, but it does not fall short of charm. Named from an Algonquian Indian word meaning "at the end of the water," the town was founded in 1765 with the construction of grist mills and tobacco warehouses.

Today, Occoquan is an artists' community, featuring shops, dining, ghost walks, boating, and fishing … all with brick sidewalks lit by old-fashioned gaslights. The historic town square may only cover six square blocks, but it is home to over 100 shops and restaurants, making Occoquan a small town with big-town convenience. While you're visiting, swing by the Secret Garden Cafe; you won't regret it! This casual restaurant in Occoquan sits in an old home from the 1840s, and the vibes and the menu are both sensational.

When it comes to the best towns in Virginia, Occoquan certainly fits the bill.

9. Farmville

Farmville sits just south of the geographic center of the state, meaning that it is "literally" in the heart of Virginia. Located next to High Bridge Trail State Park and home to Longwood University, one of the nation’s oldest public institutions, Farmville is filled with history, quaint charm, friendly people, and a high quality of life.

Every year, the town hosts the Heart of Virginia Festival, a festival where local businesses come together with vendors and musicians from around the country to provide arts and crafts, traditional foods, music, and fireworks. Recognized as a stunning town in Virginia and surrounded by natural beauty, this quaint town in Virginia serves as the area’s economic hub with local businesses, specialty shops, restaurants, and cultural activities.

10. Warrenton

Located less than an hour from Washington, D.C., and only 35 minutes from Dulles Airport, this quaint town in Virginia provides a perfect blend of new and old, urban and historical. The jailhouse and courthouse that served as the earliest beginnings of the town in 1790 have both been beautifully preserved and now serve as museum buildings housing Native American artifacts, Civil War exhibits featuring Colonel John S. Mosby (a Warrenton resident), and original jail cells.

Another key feature of Old Town Warrenton is the statue of Chief Justice John Marshall (who served from 1801–1835. Also a haven for horse enthusiasts, the Warrenton Hunt began in 1883, the Warrenton Horse Show in 1900, and the Virginia Gold Cup Race in 1922. Today, Warrenton offers a diverse history and small-town charm that make it an idyllic place to live. If you've got a sweet tooth, swing by the Red Truck Bakery and have a slice of the world's best pie.

What are your favorite small towns in Virginia? Did it make our list? If there is a town you believe deserves a spot on our list, let me know by filling out this nomination form. I'd love to hear from you.