Must-See Fall Destinations in the Washington, D.C. Area

Harpers Ferry, West Virginia | Morey Longo

Many seasonal getaways lie near Washington, D.C. for both visitors and residents to explore. Let’s look at premier fall destinations in the Washington, D.C. area for those seeking a dream autumn escape. 

Cumberland, MD

Cumberland showcases stunning scenery, a fascinating history, and a delightful small-town ambiance. During fall, orchards on the outskirts of town offer apple picking and corn mazes. For a particularly unique seasonal experience, take a ride on the Western Maryland Scenic Railroad to immerse yourself in breathtaking fall views of the Allegheny Mountains. 

Western Maryland Scenic Railroad | Byeonghoon Jeon

Annapolis, MD

Annapolis, Maryland’s capital, is a scenic and historic city along the Chesapeake Bay. Filled with historical architecture and home to the U.S. Naval Academy, Annapolis is a one-of-a-kind destination with plenty to experience. To fully embrace the spooky spirit of the season, take a ghost tour through Annapolis’s historic neighborhoods. There, you can learn about the city’s incredible history while experiencing a spine-tingling fright. 

U.S. Naval Academy, Annapolis | Cathy Cardno

Chestertown, MD

Chestertown, a tiny community along the Chester River, is a popular vacation destination thanks to its captivating history, gorgeous riverfront settings, and small-town atmosphere. Its Arts & Entertainment District hosts entertaining shows and events year-round. During fall, Chestertown’s restaurants and cafes serve up seasonal treats, and the mild weather and changing leaves create the perfect autumn atmosphere. 

Fredericksburg, VA

South of D.C., you’ll find the picturesque city of Fredericksburg, Virginia. This historic community has witnessed pivotal American battles in various conflicts, boasts centuries-old architecture, and is home to renowned historic sites. Fredericksburg embraces the season with numerous celebrations such as the Fall Arts and Craft Festival and the Virginia Cider Festival. Also, several surrounding farms provide opportunities for apple picking and exploring corn mazes. 

Fredericksburg | Nils Huenerfuerst

Georgetown, D.C.

You don’t have to leave Washington, D.C. to immerse yourself in fall splendor. Georgetown is a charming neighborhood along the Potomac River. This picturesque part of the city features cobblestone streets, historical architecture, and a celebrated food scene. Autumn transforms Georgetown’s riverfront public parks into a vibrant setting, and seasonal activities transport you to the past. For example, nighttime ghost tours showcase the community’s fascinating history, allowing you to fully embrace the Halloween season. 

Georgetown | Ana Lanza

Harpers Ferry, WV

For those looking to immerse themselves in a gorgeous natural setting this fall, Harpers Ferry is the ideal destination. This picturesque little town sits at the confluence of the Potomac and Shenandoah Rivers, surrounded by expansive wilderness. Harpers Ferry’s lush forests provide an Instagram-worthy backdrop ideal for leaf-peeping. Also, history buffs will enjoy the renowned Harpers Ferry National Historical Park, which includes historical buildings and a top-notch museum centered on the city’s remarkable past. 

Harpers Ferry | Wen Zhu

If you love all that this region offers, check out some spectacular, spacious properties in Washington, D.C. 

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