There is nothing quite as charming as a small town with a great main street and friendly people. DC may not be a small town but it is close to many. These 15 friendly small towns near Washington DC are perfect for a weekend road trip from the district!

1. Floyd, Virginia
Floyd, VA 24091, USA
Flickr/Bruce Tuten
A small town with a population of 450 people, Floyd is big on personality. It’s a one-stoplight town that is filled with bluegrass music every Friday night. The Floyd Country Store hosts the Friday Night Jamboree where locals and visitors come to enjoy the music and the fun.
2. Crisfield, Maryland
Crisfield, MD 21817, USA
Courtesy of Wikimedia/baldeaglebluff
Crisfield is definitely the place for seafood lovers. In fact, it’s called the "Seafood Capital of the World." The town is home to a little over 2,000 residents and is kept busy by many tourists who visit throughout the year. It’s a great place to rent a boat and boat over to Tangier Island or enjoy an authentic clambake or crab feast.
3. Cape Charles, Virginia
Cape Charles, VA 23310, USA
Flickr/Keith Parnell
Cape Charles is on the shores of the Chesapeake in Southern Virginia. Cape Charles has a little something for everyone. There are waterfront restaurants, charming cafes, old-fashioned soda fountains and so much more. You can shop at local shops, boat in marinas, golf at famous golf courses and learn about the history of the town at the Cape Charles Museum.
4. Hampstead Maryland
Hampstead, MD 21074, USA
Flickr/Jon Dawson
Over 6,000 people call Hampstead, in Carroll County, MD home. While it was once a farming hub, it has since grown into a bustling small town. You can enjoy nature at various parks or the nearby Cascade Lake. Or visit their downtown area and stroll by local cafes, restaurants, and shops.
5. Thurmont, Maryland
Thurmont, MD 21788, USA
Flickr/Taber Andrew Bain
Thurmont is in Northern Maryland close to Pennsylvania and is home to a little over 6,000 residents. It has a charming historic downtown area and its motto is "The Gateway to the Mountains," due to its close proximity to nature. Thurmont is home to popular hiking places Cunningham Falls State Park and Catoctin Mountain Park. It’s also the host of the Catoctin Colorfest, an arts festival that attracts over 100,000 people.
6. Oakland, Maryland
Oakland, MD 21550, USA
Flickr/Jon Dawson
Oakland is a former railroad town that features a historic and preserved B&O railroad station. Oakland is a great place to escape into nature or enjoy small-town charm. It is home to a vibrant arts scene and has one of the first designated Maryland Main Streets. It’s a few miles from Deep Creek Lake and Swallow Falls State Park.
7. Gordonsville, Virginia
Gordonsville, VA 22942, USA
Flickr/Ryan Stavely
Gordonville has a rich historic past that plays into its present-day charm. There are quaint shops and restaurants in the downtown area. You will definitely want to try the fried chicken there as it is known as "the chicken-leg center of the universe." Every year this town celebrates the "Gordonsville Famous Fried Chicken Festival," where you can enjoy history and delicious food — two staples of the town.

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8. Onancock, Virginia
Onancock, VA 23417, USA
Facebook/Town of Onancock
It’s been said that Onancock is "the Gem of the Eastern Shore." Onancock is extremely walkable. They have an incredible arts scene, live theater, music, galleries, and so much more. Outside of their downtown area, there is true natural beauty, along the creek that leads to the Chesapeake Bay.
9. Town Of Orange, Virginia
Orange, VA 22960, USA
Flickr/Jimmy Emerson, DVM
The Town Of Orange is an old-fashioned small town. They have a historic downtown filled with shops, restaurants, and historic sites. The businesses surround the Historic Orange Train Station, which was built in 1909. The 19th-century County Courthouse and the James Madison Museum are two other popular attractions.
10. Leonardtown, Maryland
Leonardtown, MD 20650, USA
Flickr/Elvert Barnes
Leonardtown is a historic town with a population of almost 4,000 people. It might be best known for the national oyster-shucking championship it holds every year. But it has much more to offer than an annual event. They have recently revitalized their quaint downtown area and have beautiful waterfront views and activities along the Wharf.
11. Emmitsburg, Maryland
Emmitsburg, MD 21727, USA
Flickr/Jon Dawnson
Emmitsburg is a college town as it’s the location of the historic Mount St. Mary’s University. It’s also a popular destination for Catholics as it is home to the National Shrine Grotto of Our Lady of Lourdes and the Basilica and National Shrine of St. Elizabeth Ann Seton. Situated in gorgeous countryside, it’s worth the drive for the views and the beautiful historic buildings!
12. Warrenton, Virginia
Warrenton, VA, USA
Flickr/John McTarngaghan
Warrenton has something for everyone! You can explore their historic downtown area and purchase unique items from local artisans. Or hike, bike, or walk along the local trails to Civil War battlefields. Located right in Virginia wine country, Warrantor is also home to fantastic wineries.
13. Washington, Virginia
Washington, VA 22747, USA
Facebook/The Town of Washington
Sometimes called "Little Washington," Washington, Virginia is a gorgeous town in the foothills of the Blue Ridge Mountains in Virginia. It is best known as the location for the highly rated Inn at Little Washington Restaurant and Inn. The town still has the same five-block by two-block it did when George Washington first surveyed it in the 1700s. But today, those blocks are filled with galleries, theaters, shops, and restaurants.
14. Occoquan, Virginia
Occoquan Historic District, VA, USA
Flickr/Mark Plummer
Occoquan in Prince William County has a population of 1,000 people. It’s seated on the banks of the Occoquan River and is rich with history and personality. The town was home to America’s first automated grist mill. Today, the streets are lined with unique boutiques and fantastic restaurants. You can also enjoy water activities on the water.
15. Middleburg, Virginia
Middleburg, VA 20117, USA
Flickr/Payton Chung
Middleburg is the nation’s Horse and Hunt Capital and was established in 1787. It’s a well-known destination for equestrian events. It’s also one of the top 10 wine destinations in the world. In between horses and wine, Middleburg features beautiful rolling hills and gorgeous landscapes.

If you’d like a charming town that’s a day trip instead of a weekend, you must visit this charming town outside of DC!

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Things To Do Near Washington DC

Sara Dager | September 23, 2022

What are the best outdoor activities in Washington DC?

While the city has an urban landscape, there are still a lot of fun outdoor activities in Washington DC that are perfect for the whole family. A walk down the C and O canal path is packed full of natural beauty and old-world charm. Or maybe you want to get out on the water? Then, take a riverboat tour of the Potomac or canoe the Anacostia. There are also outdoor movies, roller skating, and concerts to be enjoyed throughout the city.

What are the most unique places to spend the night in Washington DC?

If you are looking for unique lodging in Washington DC, there are a ton of interesting options for all sorts of travelers. You could stay at the Tabard in a chic collection of townhouses, the decor alone makes this stay worth it. Another great choice is spending a few nights in one of the themed rooms at the Mansion on O Street. Want to sleep in a log cabin one night and a mansion the next? This creative space has got your back. And keep an eye out for more than 70 hidden doors! We've also put together a list of haunted hotels in Washington DC if you prefer to be kept awake with the sounds of spirits!

Which are the best hole-in-the-wall restaurants in Washington DC? 

After a long day of exploring a new city, there really is nothing better than wandering into a restaurant that looks like nothing on the outside but serves the absolute best food. Finding the best hole-in-the-wall restaurants in Washington DC will make you feel like one of the locals. Go down the stairs to Sakuramen for the best ramen in the city or climb the stairs to El Rinconcito for El Salvadorian food that will knock your socks off. Or if you want American food, stop into the simply named Meats and Foods for a killer hot dog.

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