The best Main Streets in Virginia are in the state’s small towns. While it’s true that Virginia has some impressive big cities, it’s really the small towns that give our state so much charm and character. No matter the season, a visit to one of these places is bound to result in a newfound appreciation for the Old Dominion. And while we sincerely believe that each small town is worthy of a trip, the following is a list of cutest small towns in Virginia that have some of the best downtowns in Virginia. Ready to start exploring?

1. Abingdon
Abingdon, VA, USA
Visit Abingdon VA / Facebook
Tucked away in the mountains of southwestern Virginia, Abingdon is filled to the brim with charm. Exploring downtown, you'll find an array of friendly shops, art galleries, cozy cafes, and more. Some of the most famous landmarks include the historic Barter Theatre and the William King Museum. Learn more about what makes Abingdon such a fantastic day trip in Virginia any time of the year.
2. Bedford
Bedford, VA 24523, USA
Destination Bedford Virginia / Facebook
There's so much to appreciate about Bedford, Virginia. It's here you'll find the National D-Day Memorial, considered to be among the most famous attractions in the state. For those looking for outdoor adventures, there's no shortage of hikes, walks, and beautiful scenery surrounding the town. Peaks of Otter is one such outdoor attraction that belongs on any outdoor enthusiast's bucket list. Here's more on the outdoor adventures near Bedford, Virginia.

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3. Lexington
Lexington, VA 24450, USA
Lexington, Virginia and the Rockbridge Area Tourism / Facebook
The small mountain town of Lexington is positively loaded with history. Conveniently located off of I-81, this charming destination is relatively easy to get to. Strolling downtown, you'll find this college town is filled with antique stores, art galleries, coffee shops, restaurants, and all kinds of historic landmarks. Learn more about planning your visit to Lexington, Virginia. It's truly one of the most walkable downtowns in Virginia.
4. Staunton
Staunton, VA 24401, USA
allisonmseward12 / flickr
Did you know that Virginia was home to the American Shakespeare Center's Blackfriars Playhouse? Head to downtown Staunton, Virginia, and you'll be able to experience a play performed as it would have been hundreds of years ago. In fact, it's the world's only re-creation of Shakespeare's indoor theatre. After catching a show, enjoy one of the town's impressive restaurants, coffee shops, or gift stores. This sweet small town has one of the best Main Streets in Virginia. It has even been called one of the best small towns in America, and it's not hard to see why!
5. Middleburg
Middleburg, VA 20117, USA
Visit Middleburg / Facebook
No list of charming small towns in Virginia is complete without mentioning Middleburg. This picturesque small town has history that dates back to the Revolutionary War, and visiting is a bit like stepping back in time. The area is also known for its pristine natural surroundings, which lend themselves to wineries and horse farms. While you're in town, be sure to visit the Red Fox Inn & Tavern. Established in 1728, it's among the oldest taverns in the entire country. For more inspiration on planning your trip to Middleburg, you can check out our previous article: It's Impossible To Drive Through This Delightful Virginia Town Without Stopping.

So what do think about these charming small towns in Virginia? We know we barely scratched the surface, so be sure to share some of the downtown areas you enjoy visiting the most! For even more small-town love, check out our list of the best Main Streets in Virginia.

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More to Explore

small towns in Virginia

Jessica Bohl | September 16, 2022

What are some great tiny towns in Virginia worth a visit?

There are hundreds of tiny towns in Virginia, meaning towns with populations of less than about 1,000 people. But just because they may be small does not mean these towns aren’t worthy of a visit. Take, for instance, the tiny town of Scotland. With just about 100 residents this charming river town is great for bird watching and soaking in the lovely ambiance. So hop aboard the Jamestown-Scotland ferry and enjoy the peaceful ride across the James River. Fincastle is a tiny town with big history. This town of barely 350 residents is where Lewis and Clark set out to explore the Louisiana Purchase. It’s also home to the historic courthouse designed by Thomas Jefferson.

What are some picturesque small towns in Virginia?

If you are moved by small towns that are picture-perfect, there are plenty in Virginia you will want to visit. Chincoteague is a beautiful, small coastal town. With pristine beaches and lovely sunrises, it’s worth checking out for a day or the weekend. With streets lined with post-Victorian houses and shops, Cape Charles is as photo worthy as they come. Sitting near the mouth of the Chesapeake Bay, this charming seaside town will transport you to quieter, quainter times.

What are some friendly small towns in Virginia?

If you’re looking for a small town where everyone knows your name, then you will love some of Virginia’s small towns. Luray is known for its famous caverns, but locals also love its live music, local winery, and Jazz-era hotel. Floyd is another friendly town in Virginia. There, you’ll find homemade meals, porch-pickin’, and handmade crafts. It’s a welcoming place you will want to check out!

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