I have to be honest: even though I’m a Baltimore gal, Virginia easily wins over Maryland for best small towns. Its history is mush better preserved and there’s a diverse landscape from the bayside to the Blue Ridge Mountains (a place said to be among the most beautiful in the entire world).

I’ve been to Virginia several times, but I decided to go around, driving to the state’s small towns to experience them for myself. These are the ones that made the cut to this blog post, the ones I found most charming and worthy of a recommendation.

So without further adieu, here’s my list of cute towns to visit in Virginia.

Note: This post has been in my drafts for a looong time pending visiting, and returning, to a number more towns in Virginia. So this is definitely not an exhaustive list and more will be added as I visit, but for the time being, these are the ones I have visited to help inspire you in your Virginia travels.

Charlottesville, Virginia

History: Charlottesville had been inhabited by the Monacan peoples before the colonists came. It was a very small place after the colonists settled there and became the home of Thomas Jefferson in 1768. Circa 1800, the area became a planned, gridded town and 1819 saw the founding of the University of Virginia. The town grew after the introduction of the railway system and also survived the Civil War.

Today: Charlottesville is a very vibrant town with a lot of places to shop and dine. It has the downtown area, which is very popular with the youth because, you know, the University of Virginia. There’s lots of bars, restaurants to visit, local stores – including some great antique shops – and just an overall vibrant vibe. I think it’s quite different from how people might imagine it to be.

Things to do: Aside from visiting the cute town, the most popular thing to do in Charlottesville is visit Monticello. You can also stop by the University of Virginia to see the architecture, and even the room in which Edgar Allan Poe stayed.

Chincoteague, Virginia

Right next to Maryland is a cute town called Chincoteague. But the town isn’t the main draw here: it’s special breed of ponies.

History: Until fairly recently, Chincoteague was not largely inhabited because of its marshy area and was rather used as an area to store livestock and hunt shellfish. In the 19th century, the local ponies called “Chincoteague ponies” (also called “horses”) swam across the channel after being bred and this became a yearly tradition. In 1925, the town burned down in a fire and the pony swim was marketed to bring tourists to the area to raise money to rebuild the town.

Today: Chincoteague is still a very small place but it’s definitely worth the trip out to see the wildlife and the ponies. The town is quite small but has a few local shops to explore and one of my favorite beachside past-times: mini golf.

Things to do: The big must-do is the Chincoteague National Wildlife Refuge, which is a large refuge which supposedly houses the Chincoteague ponies. Unfortunately I’ve never personally seen any ponies there, which is why I always recommend the Chincoteague Pony Center, which has guaranteed pony sightings.

Click here to see my Chincoteague travel guide.

Culpeper, Virginia

History: In the 18th century, the area was owned by the Culpeper and then by marriage Fairfax family. That’s not interesting in itself, but they commissioned a 17-year-old George Washington to survey the land, which is indeed quite interesting. During the Revolutionary War, the Culpeper “Minute Men” militia was formed.

Today: Culpeper’s a cute town with several restaurants and small stores with the Blue Ridge Mountains visible in the distance. The charming old town, which looks like it dates to the 19th-20th centuries, is quite small at two or three blocks, but it was filled with cute stores and restaurants open on a Sunday, so I just had to add Culpeper to the list. It’s a cute place!

Things to Do: Culpeper is surrounded by battlefields to visit, including Cedar Mountain and Kelly’s Ford. There’s a small Museum of Culpeper History if you’d like to get to know more about the town, plus the Bergandine House (18th century).

If you’re interested in Civil War history, a few miles away is the Graffiti House which had a large amount of Civil War-era graffiti inside. The building is thought to have been a hospital and patients wrote and drew things on the walls.

Fredericksburg, Virginia

Fredericksburg is easily considered one of Virginia’s most beautiful and historic towns – and it’s very easy to see why.

History: The area that makes up Fredericksburg today was originally used for hunting and fishing by the Mannahoak tribe. It was colonised shortly after Europeans came and the proximity Rappahannock River made it a popular port particularly for the tobacco trade. In 1728, Fredericksburg was made an official port. It was a center for munitions creation during the Revolutionary War and again saw war in the 1860s. The Battle of Fredericksburg was fought in December 1862.

Today: Fredericksburg is an excellent example of a town that has retained its historic integrity while being modernised. A lot of the beautiful federal buildings still stand. Some may not like this, but many were outfitted in the 20th century with large storefront windows (I’m not sure what the architectural term is), so there’s also a taste of the 20th century – something I personally like. Several of the buildings have been painted too.

It’s also quite central between DC and Richmond and other areas of interest in northern-ish Virginia. It would make a great base if you’re looking for a place to stay to explore Virginia’s colonial and civil war history.

Things to do: There’s quite a bit of antique shopping to be done in Fredericksburg. You can also see colonial era history at the Mary Washington House (where George Washington’s mother lived) and the Rising Sun Tavern which dates to 1792. There are also the colonial homes Kenmore Estate, which is very beautiful, and Chatham Manor which I’ve yet to visit. You can also get a fill of Civil War era history at Fredericksburg Battlefield.

Leesburg, Virginia

History: Leesburg was founded in 1758 when it became the seat of Loundoun County and the town was planned around the courthouse. The area became quite prosperous and continued to grow and maintain its economic stability due to its proximity to Washington, DC (just as it maintains today).

Today: Leesburg is a very cute town with a big 19th century feel. It’s very lively and has a lot of locally-owned shops and restaurants. Leesburg is also located in Virginia’s wine country so it’s a popular wedding destination. Note that you might need to make reservations or check with certain restaurants before visiting as they can often close for wedding parties.

Things to Do: Leesburg is more known for its surrounding wineries, so after a visit to the town, you can head on a road trip to explore some wines. In town, you can stay and learn some of the city’s history at Dodona Manor. I’ve never been because it’s expensive, but for years I’ve wanted to go to The Conche, which is a chocolate-based restaurant. It looks exquisite.

Leesburg also hosts lots of events. I happened to go to their Flower & Garden Festival in April which was a good time. Be sure to keep an eye out for other events.

Lexington, Virginia

History: Lexington was established in 1778. Washington & Lee University (then Augusta) had been established before in 1749 and Lexington later became the home of the Virginia Military Institute in 1839. It’s always been a college town. It witnessed the Civil War and was the home and final resting place of Stonewall Jackson.

Today: Lexington’s one of the bigger places on this list but still a college town. It’s definitely one of the most charming places on this list to me and retains its 19th century heritage the best. I most recently visited on a Sunday which was apparently a bad choice because most everything was shut, but I still enjoyed walking along the streets and seeing the cute stores and lovely buildings.

Things to Do: Both university have museums. The Museums at Washington & Lee University has a chapel and a handful of art museums open on weekdays, and the Virginia Military Institute Museum has a museum on different aspects of Virginia’s military past – including the preserved horse of Stonewall Jackson (which may or may not be a traumatic childhood memory of mine!).

You can learn some local history at the Campbell House and a little outside the town center is the Miller’s House Museum. Probably the most notable thing to do is visit the Stonewall Jackson House and Museum, where the Confederate general once lived. (I didn’t visit because I’m not a fan, but maybe I should have?)

Middleburg, Virginia

History: Colonists had used Middleburg as a resting point since the early 18th century but it became an established town in 1787. It’s also steeped in Civil War history and later, Civil Rights history when John F. Kennedy visited to campaign for Civil Rights.

Today: Middleburg is a small but quite charming town with a handful of restaurants and a bunch of locally owned stores. I remember when I visited, I felt a bit out of place since Middleburg seems a lot more bougie than the places I normally visit – and what I’d expect from rural-ish Virginia. I think it’s because the area is known for horse races. The town itself is also not that big, but it really stuck with me because I loved all the stone buildings – and there’s quite a few of them. It’s definitely a place to keep on your list.

Things to Do: One of the main things to do in Middleburg is see its local shops, many of which sell fine antiques and art. There’s the Red Fox Inn which is said to be one of the oldest in the United States. I’d love to eat there but I cannot afford it (again, bougie!). Another draw of Middleburg is the horse racing and the National Sporting Library & Museum but if you read my blog, you’ll know I don’t support that kind of thing.

Occoquan, Virginia

History: The Occoquan area had long been settled by the Doeg tribe when European colonists came. In 1700, the English started erecting tan yards, mills and warehouses where Occoquan currently stands. It operated as an industrial town for centuries. A huge fire destroyed much of the town in 1916 and the mill burned down a few years later, but the town rebuilt and continued to maintain its industrial heritage.

Today: The town is one of the cutest, quirkiest places I’ve ever been. I actually remember visiting as a kid and thinking, “wow! I’ve never seen a place like this before!” The mix-matched architecture tells its centuries-old story, from colonial stone buildings to 20th century houses, and Victorian and even Tudor revival styles. Many buildings utilise their upper stories so it’s also one quite vertical. There are several cute, locally owned shops and a few places to eat if you come to explore Occoquan.

Things to Do: You can stop into the small Mill House Museum to see some of the town’s history. Something fun to do is explore the Occoquan River via kayak with Penguin Paddling. They’re right on the boardwalk, which you can also walk along on your own to take in views of the river. You can also dine on the waterfront at a handful of restaurants.

Staunton, Virginia

History: Staunton has a bit earlier colonial history, having been established in 1732. In the mid 19th century it became a transport hub because of the railroads – which you can quite clearly see with the old train station and the architecture dating to the heyday of the railway.

Today: Staunton is probably one of the biggest places on this list. The town itself is quite large but even the old town section (the part I always focus on) is several blocks in each direction. It feels like walking in the 19th-20th centuries but with a modern touch. There are several shops and a few places to eat, including including the Staunton Antique Center. It reminds me very much of Frederick, Maryland, so if that’s a place you like then you’ll probably also like Staunton.

Things to Do: Staunton’s one of the bigger towns on this list. Take the time to really walk around and see its historic districts. One of the most notable things to do in Staunton is the Woodrow Wilson Library and Museum which is where Woodrow Wilson was born. Outside the old town there’s also the Frontier Culture Museum giving a glimpse at colonial life. I didn’t have time for it so I’ll have to go back!

Warrenton, Virginia

History: Warrenton grew as a small development around the time of the Revolutionary War. It grew in the 19th century and was very close to many battles of the Civil War. Warrenton had always seen development, even though on a slow and small scale, from its founding till today. However lots of the town by a fire in 1909.

Today: “Warrenton” encompasses a large area of suburbia, but the historic downtown is the focus here. It’s a bit small but very cute and even though Warrenton dates to much earlier, the old town gives a feel of the 21st century built on bones of the past. There are several local places to shop and eat. Every time I’ve been, there’s been a lot of people out and about.

Things to Do: Warrenton has a Farmer’s Market during the warmer months. The Old Town is also home to many events, so definitely have a look at that before visiting. I got to visit during their Juneteenth festival, which was quite fun.

Williamsburg, Virginia

History: Williamsburg was inhabited by the Powhatan tribe before colonisation. Afterword, the colonial town of Williamsburg became the capital of Virginia in 1699. It grew and even hosted America’s first legislative assembly until 1780, when the capital changed to Richmond. The town grew poorer and less relevant over the decades until 1900, when Reverend Dr. W.A.R. Goodwin decided to turn the town into an open-air museum.

Today: Historic Williamsburg is absolutely adorable and looks original. It’s a fun place to walk around, where you can enter shops that sell colonial-themed wares, and see live demonstrations and tours from actors in colonial garb. The town also has some high-end shopping and several places to eat.

Things to do: Visiting Colonial Williamsburg is without a doubt the draw of the town. It’s a very charming and rather large setup. The town is free to walk around but many of the attractions require you to purchase a ticket (one ticket to the colonial center should grant you access to almost everything). And if you’re a fan of amusement parks then you absolutely have to go to Busch Gardens Williamsburg. They have great rides and their theme is European countries, so you can travel to seven countries in one day!

Click here to view my Williamsburg travel guide.

I hope this guide helped you plan your trip to Virginia and that you enjoy these towns as much as I did!

What are some of your favorite places in Virginia you’d add to this list?

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