The Legislative building in downtown Dover, Delaware. Editorial credit: Nagel Photography / Shutterstock.com.

6 Best Downtowns In Delaware

Although it’s known for its picturesque natural areas, such as state parks and beaches, Delaware is home to many small towns with thriving downtown areas. With eateries, pubs, cafes, galleries, museums, antique shops, and street markets in towns such as Lewes, Georgetown, and Dover, the downtown areas in these towns are a hive of historical and commercial activity. Visitors looking for a lively atmosphere mixed with small-town life can enjoy activities such as learning about local history, sampling local cuisine, or shopping for souvenirs, making a trip to the First State unforgettable.

Lewes

View of downtown Lewes Deleware from the canal.
View of downtown Lewes Deleware from the canal.

Lewes is a small town that offers gorgeous views of the Delaware Bay and Atlantic Ocean coastline. Beyond the breathtaking scenery of the serene waters, its downtown area is one of the best in the state. The Lewes Historic District is renowned for its restored houses and buildings that showcase its rich past. Begin at the Cannonball House, which dates back to the 18th century. It’s the only building in Lewes that survived damage from the War of 1812 bombing of Lewes. Today, the house is home to the Lewes Historical Society’s maritime museum with artifacts, including a Fresnel lens that once served in Delaware Bay’s Fourteen Foot Bank Lighthouse. The Zwaanendael Museum, another historical museum featuring maritime exhibits from the Lewes area, is a short distance from the Cannonball House.

The downtown area is filled with history and features an incredible mix of dining and shopping establishments. Lewes Oyster House, where fresh oysters, sea scallops, shrimp, salmon, and lobster dishes are highlighted on the menu, is ideal for seafood lovers. Downtown Lewes also has charming coffeehouses like Lewes Bake Shoppe & Notting Hill Coffee Roastery, which offers freshly roasted coffee and delicious pastries. Like any downtown area, there are unique stores and boutiques where endless shopping awaits. Buy gourmet chocolates at Edie Bees Confection Shop, find rare collectibles at Lewes Mercantile Antiques, or browse trendy clothing at Blooming Boutique—downtown Lewes has it all.

Georgetown

The Circle in Georgetown, Delaware
The Circle in Georgetown, Delaware. Editorial credit: duckeesue / Shutterstock.com.

Unlike other Delaware towns, Georgetown boasts a unique circular layout at its center, aptly named The Circle. This area, nestled in the heart of downtown, is surrounded by many historic structures, including the Georgetown Town Hall and the Sussex County Courthouse. After a historic district tour, don’t miss the chance to visit nearby eateries and shops, such as the Georgetown Family Restaurant and Wilson’s General Store. The Circle also serves as a vibrant hub for events, including Return Day, a celebration that follows the general election in November every two years. Tens of thousands attend this event, featuring a festive parade and other celebratory activities.

The downtown area’s attractions include museums like the Marvel Carriage Museum, which has a fantastic collection of vintage carriages. A one-room schoolhouse from the 1800s is among the genuine and restored buildings from Georgetown’s rich past on display at the museum. The Delaware Aviation Museum, another highlight, features military aircraft and artifacts.

Dover

State Capitol Building in Dover, Delaware
State Capitol Building in Dover, Delaware. Editorial credit: Dennis MacDonald / Shutterstock.com.

Dover, the capital of Delaware, is steeped in history and boasts a vibrant art and cultural scene at the heart of its downtown area. Begin your exploration at the Old State House in The Green, a historic district that’s the very center of Dover. Take a guided tour of this iconic landmark, built in 1791 as Delaware’s capitol during the United States’ formative years. For a deeper dive into Dover’s past, the Johnson Victrola Museum is a must-visit, showcasing the history of recorded music and the pioneering work of Eldridge Reeves Johnson in early sound recording.

Dover’s downtown area is also home to the Biggs Museum of American Art, a haven for art enthusiasts. While there, be sure to browse the collection of decorative art and rotating exhibits. For a historic and charming lodging option, consider the State Street Inn in the heart of the city. Downtown Dover also comes alive with events, such as the Dover Days Festival, the Capital Crawl, and OktDoverfest, the town's version of Oktoberfest.

Delaware City

Delaware City Hotel, in the Delaware City Historic District
Delaware City Hotel in the Delaware City Historic District. Image credit: Smallbones via Wikimedia Commons.

Located on the banks of the Delaware River at the eastern end of the Chesapeake and Delaware Canal, Delaware City is a beautiful waterfront town worth visiting. In addition to exploring water activities, such as boating, at Delaware City Marina, this town offers many restaurants, stores, and galleries, all within walking distance of each other in its downtown area.

Sunday's Cafe 64, a staple brunch spot downtown, is only open on Sundays, hence the name. Another downtown dining favorite is Crabby Dick’s, which is famous for its crab legs and crab dishes, as well as other seafood options like shrimp, oysters, and fish. It also offers a weekday happy hour menu, daily specials, and Sunday brunch. Saturdays and Sundays are for shopping at Delaware City Trading Company, which carries everything from general goods to specialty products. A stop at Artworth Creations, a gallery showcasing the colorful and meaningful artwork of talented artist Ainsworth McKend, is also a must in downtown Delaware City.

Smyrna

Downtown Smyrna, Delaware
Downtown Smyrna, Delaware. Image credit: Acroterion via Wikimedia Commons.

Smyrna’s small-town charm is highlighted by its downtown district, which features attractions like the Smyrna Museum. Owned and operated by the Duck Creek Historical Society, the museum is housed in a building that quartered soldiers during the War of 1812, offering insight into Delaware’s historical architecture. After exploring the museum, take a short walk down the block to attend a Broadway show or concert at the beautifully restored Smyrna Opera House, a premier performing arts venue.

Additionally, downtown Smyrna has many diverse restaurants along its streets, including Italian classics at Trevi Ristorante, Irish and American fare at Sheridan’s Irish Pub, barbecue staples at GuzzyQ, and fresh subs from Main Street Market. For an authentic Smyrna drinking experience, head to Painted Stave Distilling. It’s the perfect place to sip on locally made spirits like bourbon, vodka, and gin. Painted Stave also hosts cocktail pairing events and mixology classes, combining fun and drinks in the heart of downtown Smyrna.

Milford

Walnut Street in downtown Milford, Delaware.
Walnut Street in downtown Milford, Delaware. Image credit: Tim Kiser via Wikimedia Commons.

Milford, located on the banks of the Mispillion River in southern Delaware, has one of the best downtowns in the state. Among its highlights is the picturesque, mile-long Mispillion Riverwalk, which extends through downtown Milford, where some of the best dining, shopping, and attractions are located. For a fun place to eat and socialize, visit Fondue, which offers a multi-course fondue dining experience, a cocktail menu, and live music. Other establishments include La Hacienda Milford Restaurant, where you can indulge in the flavors of Mexico, and Benvenuto, which takes you to Italy with its menu of Tuscan-inspired dishes.

Downtown Milford is home to unique stores like Irish Rose, offering shoppers a taste of Irish culture, and Red Bandana, which sells vintage toys and games. To dive into Milford’s history, stop by the Milford Museum, which has thousands of artifacts and exhibits from the shipbuilding to the military. Downtown Milford also hosts several events, including the Riverwalk Farmers Market, held from May through October, and the annual Holiday Stroll & Christmas Market during the holiday season.

Discover The Best Downtown Areas In These Delaware Towns

Experience the sights, sounds, and flavors of unique main streets and commercial hubs in the small towns of Lewes, Georgetown, Dover, Delaware City, Smyrna, and Milford, where the scenes are slow-paced yet vibrant. While in these Delaware towns, admire the historic architecture, shop at quaint boutiques, indulge in regional cuisine, and get a glimpse of the past by visiting ancient buildings or museums. After a satisfying downtown tour, don’t forget to head outdoors to enjoy breathtaking landscape views and the abundance of recreational activities throughout the First State.

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