The D.C. region is home to some of the most incredible city centers in the U.S. Let’s discover some charming Washington, D.C.-area downtowns with a vast array of things to see and do.
Frederick, MD
Frederick is a charming city known for its historical buildings and winding waterways. Downtown Frederick hosts over 200 local businesses, many local galleries, and abundant food options, breweries, and distilleries. During the holiday season, the beautifully decorated downtown hosts festive events that promote local businesses as part of its December Saturdays program.
Chestertown, MD
Chestertown, a historic small town along the Chester River, showcases centuries-old architecture and serves as a beloved year-round hotspot. Main Street Chestertown has a classic look with brick buildings that house local businesses and quaint cafes. Known for its communal spirit, several events take place in the downtown area throughout the year. Don’t miss out on Chestertown during the holiday season, when it hosts its annual Dickens of a Christmas event.
Ocean City, MD
Ocean City, a picturesque beachfront community, is one of Maryland’s most popular summer destinations. But beyond its sandy shoreline, visitors will also love the community’s downtown area. A majority of Ocean City’s downtown is on an expansive boardwalk. Crowds of people visit its numerous dining destinations, entertainment venues, souvenir shops, and more. This lively city hosts community events year-round, including the Christmas Carnival.
Charles Town, WV
Charles Town is a historic community steeped in charm and West Virginia’s renowned natural beauty. Its vibrant downtown core has eclectic art galleries, local businesses, and picturesque parks. Also, with buildings dating back centuries, Downtown Charles Town has earned a spot on the National Register of Historic Places.
Lewes, DE
Lewes is a spectacular coastal town and one of Delaware’s most popular getaway destinations. Its maritime legacy dates back centuries, but today, many go for Lewes’s picturesque downtown streets. Downtown Lewes features artisan stores, antique shops, and renowned restaurants serving locally caught seafood dishes. It transforms into a festive paradise during the holiday season with the Lewes Holiday Village & Market, attracting numerous visitors.
Rehoboth Beach, DE
Rehoboth Beach, another coastal Delaware destination, attracts throngs of visitors throughout the summer with its charming boardwalk and stunning beaches. Any time of the year is ideal for exploring the Rehoboth Beach downtown area. It features several boutique shops and delicious eateries with gorgeous views of the surrounding waterfront scenery. Although it is a busy summer destination, festive holiday decorations transform Rehoboth Beach into a delightful seasonal getaway.
