Whether you want to take a quick day-trip from the District to get away from the chaos of the city, or are hoping to take a weekend to disconnect and enjoy some of the beautiful small towns not too far from the District during the fall, here are some of the places that you definitely need to visit at least once!
Harpers Ferry, West Virginia
A small town located in the middle of a National Historic Park, just about 1.5 hours from the District, Harpers Ferry, WV, was ranked one of the very best fall getaways in the nation this year.
Its combination of unique colonial history, stunning natural sights, and charming small town boutiques makes it a perfect spot for a getaway this fall.
Middleburg, Virginia
Known for the Middleburg Film Festival, which takes place every October.
The town of Middleburg is one of the most charming small towns in the area, located in the midst of Virginia’s wine country.
If you don’t feel like staying in one of the cozy inns or bed-and-breakfasts in town, you can stay at the only ‘Forbes Five-Star Spa’ in Virginia, the Salamander Resort & Spa.
Annapolis, Maryland
While perhaps not the most “small town” on the list, a trip to the “Sailing Capital of America” might surprise you with just as much charm and joy as any other town on this list!
Aside from the two incredible boat shows that Annapolis hosts every fall, there is some incredible American history, stunning sites, and plenty of fun activities to keep you entertained for more than just a few days.
While you’re in town, we recommend checking out Middleton Tavern, the oldest continuously run restaurant in Maryland. It was a common socializing and dining destination for the founding fathers of America, not long after the Treaty of Paris was ratified.
Lovettsville, Virginia
Known as the most laid-back town in America, here you’ll find some of the best vineyards in the state, an incredible distillery that also happens to churn out some delicious barbecue, and, of course, some of the most stunning fall foliage around!
Staunton, Virginia
Famous for having the only replica of Shakespeare’s indoor theatre in the world, this small town is considered a hidden gem of culture and arts tucked away in the Shenandoah Valley.
Additionally, this town is a great destination for foodies, as the local restaurant “Maud and the Bear” was featured in The New York Times’ 2025 list of the nation’s best restaurants.
Thurmont, Maryland
Host of the ‘Catoctin Colorfest’ every October, one of the biggest craft festivals on the East Coast, Thurmont is a quaint mountain town just a few miles away from Camp David, the famous presidential retreat.
Head out for hikes through Catoctin Mountain Park, Cunningham Falls State Park, or the Thurmont Vista Trail to take in the sights of the season.
Williamsburg, Virginia
Dubbed the “Pancake Capital of the World”, you may know Williamsburg for its rich history and famous ‘old town, but the truth is that this small town is the best brunch destination around!
Stop by any of the nearly dozen specialized pancake houses for a breakfast that will have you happy for the rest of the day.
The perfect time to come is early fall, around late September, when the town hosts its new “Pancake Festival” in celebration of the town’s flapjack fanaticism.
Berkeley Springs, West Virginia
Touted for having some of the best-tasting tap water in the entire world, Berkeley Springs, WV, is the oldest spa town in the nation, making it a fun, relaxing, and fascinating historic town well worth a visit!
The town dates back to 1776, when it was a favorite of America’s first president, George Washington, who recorded regular visits to the town’s spa in his personal journal over the years.
Luray, Virginia
Located just two hours from the District, Luray is home to the biggest cavern system in the eastern United States, an incredible site which actually includes “The Great Stalacpipe Organ”, which is famous for being the biggest musical instrument in the entire world!
Aside from the incredible caverns, which alone are worth the trip, there are many other amazing things to do in the area:
- Check out the Shenandoah Heritage Village (included in the cavern ticket package)
- Delve into Shenandoah National Park
- Go ziplining at Bear Mountain Ziplines
Winchester, Virginia
There is no better place than the Shenandoah Valley for small-town charm!
Winchester is also technically a city, but Old Town Winchester, at the heart of the city, feels more like the warm hug of a small, homey town.
It’s filled with cultural events, pop-ups, plays, musicals, and live entertainment from locals year-round!