Looking to escape the hustle and bustle of city life? Just beyond the city limits of Washington, D.C., you’ll find charming small towns brimming with character. Whether you’re craving cobblestone streets, riverfront strolls, or historic charm, the area surrounding the city is home to some truly delightful small towns that feel like hidden gems.
Here are our top five favorite small towns near D.C. that are perfect for a day trip, weekend getaway, or spontaneous adventure.
1. Harpers Ferry, WV
1H 20M from Washington DC
Located where the Potomac and Shenandoah rivers meet, this historic small town is best known for John Brown’s 1859 raid on the federal armory, an event that became a flashpoint leading up to the civil war. Today, visitors can explore its well-preserved 19th-century architecture and scenic riverfront views.
Things to do:
- See John Brown’s Raid: originally built in 1848 as the fire engine and guard house for the U.S. Armory, it became famous in 1859 when abolitionist John Brown and his followers seized it during their raid on the Armory.
- Stand on Jefferson Rock: Enjoy panoramic views from the spot where Thomas Jefferson once stood and was so struck by the scenery himself, he wrote, “This scene is worth a voyage across the Atlantic.”
- Visit Harpers Ferry Adventure Center: enjoy a variety of outdoor activities including zip lining through treetops, tubing down scenic rivers, and tackling a multi-level ropes course.
- Enjoy Views at St. Peter’s Roman Catholic Church: Built in 1833, this Victorian Gothic style church is one of the few buildings in Harpers Ferry to remain largely unscathed during the Civil War.
Discover on Winding Roads & Historic Gems
2. Old Town Alexandria, VA
19 minutes from Washington D.C.
This nearly 300-year-old waterfront district is best known for its cobblestone streets, well-preserved 18th and 19th century architecture, and vibrant mix of boutique shops, acclaimed restaurants and cultural attractions. It’s a must-visit destination for history buffs, food lovers, and those seeking a quintessentially charming small-town feel.
Things to do:
- Explore King Street: Stroll along this historic main street lined with boutique sops, cozy cafes, and top-rated restaurants, or hop on the free King Street Trolley for a scenic ride!
- Visit the Stabler-Leadbeater Apothecary Museum: Founded in 1792, this apothecary once served figures like George Washington, and has been beautifully preserved with original medicine bottles, herbs, and medical equipment.
- See Art at the Torpedo Factory Art Center: Located in the former World War II torpedo factory, this art center is home to over 80 artist studios, rotating galleries & exhibits, as well as workshops and events.
- Gadsby’s Tavern Museum: named after prominent tavern keeper John Gadsby, this tavern turned museum dates back to 1785, offering a glimpse into colonial life with period furnishings, guided tours, and a rich history of hosting prominent figures like George Washington.
3. Middleburg, VA
1 hour from Washington D.C.
Nestled in the heart of Virginia’s horse and wine country, Middleburg is a charming small town known for its equestrian heritage, historic charm, and scenic countryside. Established in 1787, it boasts beautifully preserved 18th- and 19th- century architecture, boutique shops, art galleries, and cozy inns.
Things to do:
- Visit the National Sporting Library & Museum: this renowned research library and fine art museum hosts an extensive collection of over 200,000 books, manuscripts, paintings, and sculptures, with some pieces dating back to the 16th century.
- Take a Tour of Aldie Mill: Built between 1807 and 1809, the mill was once a cornerstone of the region’s agricultural economy, and now offers engaging guided tours that bring its history to life in a picturesque setting.
- Enjoy a Wine Tasting at Cana Vineyards & Winery: Located in the beautiful Loudoun County countryside, the estate features a porch, patio, and second-floor tasting room to enjoy Cana wines while taking in the breathtaking views.
- Dine at the Historic Red Fox Inn & Tavern: Established in 1828, this is one of the oldest continuously operating inns in the U.S. that serves delicious, seasonal dishes inspired by Virginia’s rich culinary traditions.
Discover on Tiny Town Tour
4. Berlin, MD
2H 40M from Washington DC
Located just a few miles inland from Ocean City, this charming small town is known for its beautifully preserved historic district and welcoming, small-town atmosphere. With roots dating back to the 18th century, Berlin features gorgeous tree-lined streets, Victorian architecture, and a vibrant downtown filled with tons of unique shops, galleries, and restaurants. Berlin has also been used as a backdrop for films like Runaway Bride and Tuck Everlasting.
Things to do:
- Experience magic at the Mermaid Museum: this whimsical one-of-a-kind attraction celebrates the lore, history, and pop culture of mermaids, offering an eclectic collection of artifacts, artwork, and exhibits that explore mermaid myths from various cultures.
- Step back in time at Calvin B. Taylor House Museum: This restored 19th century house was once the home of Robert J. Henry, who played an important role in bringing the railroad to Berlin. Today, it showcases Berlin’s rich history and hosts various events throughout the year.
- Indulge at Windmill Creek Vineyard & Winery: this charming family-owned winery is set on a historic 1858 estate where guests can enjoy wine tastings, explore the scenic grounds, and indulge in delicious food.
- Explore Berlin Main Street: this historic district features 75 establishments including boutiques, art galleries, antique shops, coffee houses, bakeries, and more.
5. Occoquan, VA
40 Minutes from Washington DC
Nestled along the Occoquan River, this historic riverside town evolved from a bustling mill town to a vibrant community known for its rich history and artistic flair. Today, visitors can enjoy the town’s well-preserved 19th-century architecture, local boutiques, art galleries, and quaint eateries.
Things to do:
- Explore the Mill House Museum: Delve into the town’s history at the Mill House Museum, housed in a historic stone building that once served as a gristmill in the 18th century. Today, this historic structure houses a collection of historic documents, photographs, and artifacts showcasing the town’s history. Plus, it’s free admission!
- Visit Mamie Davis Park: Located at the intersection of Washington Street and Mill Street, this quaint park features a cute gazebo and connects to the town’s public boardwalk and pier, perfect for an evening stroll.
- Stroll Through River Mill Park: this one-acre riverfront park offers stunning views of the Occoquan River and a peaceful atmosphere that’s perfect for a relaxing walk. The park is a favorite spot for locals and visitors alike to unwind, take photos, or enjoy a quiet moment by the river.
- Visit the Occoquan Bay National Wildlife Refuge: located just a short drive from town, this area offers a mix of wetlands, forests, and grasslands, providing habitats for over 220 species of birds and other wildlife. It’s an excellent spot for birdwatching and hiking.
Discover on Charming Curiosities
Sign up for the Guess Where Trips newsletter to get trip ideas and inspiration delivered straight to your inbox!
