7 Old-World Towns To Visit In Delaware

Delaware, “The First State,” offers travelers a glimpse into the past through its charming old-world towns. Steeped in history, these towns showcase beautifully preserved architecture, rich cultural sites, and outdoor recreation opportunities that highlight the state’s unique heritage. Whether you are strolling through cobblestone streets, exploring museums, or enjoying scenic natural landscapes, Delaware’s old-world towns provide an unforgettable journey back in time. Here are seven towns in Delaware that are perfect for those who appreciate history, architecture, and vibrant culture.

New Castle

With a population of just under 6,000, New Castle is a small town with big historical significance. The town’s colonial architecture is perfectly preserved, especially around The Green, a central park surrounded by 18th-century buildings. The 1732 New Castle Court House, a National Historic Landmark, served as the location for the state’s first court session and offers fascinating tours about Delaware's history. Nature lovers can enjoy a walk along the Battery Park Trail for beautiful views of the river and the nearby marshes. For dining, Jessop’s Tavern is a popular spot that serves hearty meals in a colonial-style setting, perfect after a day of exploring.

Lewes

Founded in 1631, Lewes is known as "The First Town in the First State," a title that highlights the historic roots of this community of around 3,500 residents. The town features charming streets lined with colonial-era homes, and the Zwaanendael Museum provides visitors with insight into the town’s Dutch colonial past. Cape Henlopen State Park, located just outside the town, offers visitors miles of pristine beaches, nature trails, and opportunities for birdwatching. For a taste of local cuisine, the waterfront area boasts several eateries, including The Wheelhouse, where you can enjoy fresh seafood while looking out over Lewes Canal.

Dover

Delaware's capital city, Dover, has a population of just under 40,000, yet it still maintains a full share of small-town charm. One of Dover's main historical attractions is the Old State House, where the state legislature met from 1791 until the 1930s, and which is now a museum. History enthusiasts will also enjoy visiting the Air Mobility Command Museum, located at Dover Air Force Base. For outdoor recreation, Silver Lake Park offers excellent opportunities for fishing, kayaking, and picnicking. During the springtime, the Dover Days festival provides a fun-filled event for locals and visitors alike, complete with arts and crafts vendors, a parade, and live entertainment.

Middletown

Middletown, with a population of around 24,000, offers a lovely mix of historic sites and modern conveniences. The town is home to the 1932 Everett Theater, a classic building that still serves as a venue for local events and exhibitions. Visitors will also find plenty of outdoor recreation opportunities at the nearby Lums Pond State Park, where they can enjoy hiking, fishing, and horseback riding. Middletown’s main street is filled with local shops and restaurants, including The Middletown Diner, a local favorite known for its hearty breakfasts and family-friendly atmosphere. The town also hosts community events like the Middletown Peach Festival, celebrating the area's agricultural history.

Odessa

Middletown’s neighbor, Odessa, is a little town of just over 400 with a wealth of well-preserved 18th and 19th-century architecture. A must-see attraction is the Historic Odessa Foundation, which maintains several buildings from the 18th century, including the Corbit-Sharp House, where visitors can learn about Odessa’s early history. If you are visiting during the winter holiday season, check out the annual Odessa Christmas Tour of Homes, where residents open their historic homes for tours and give a rare glimpse into the town’s past. Odessa also offers several great eateries, including the Odessa Diner and Cantwell’s Tavern.

Milton

Milton, with a population of just under 3,000, is a hidden gem in Delaware. The town has a fascinating history, with landmarks like the Milton Historical Society, located in a former church, providing insight into the town’s development during the 19th century. For nature lovers, Prime Hook National Wildlife Refuge is just outside the town and offers excellent opportunities for birdwatching and hiking. Milton is also home to the Dogfish Head Brewery, one of Delaware’s most popular craft beer destinations. The town’s Milton Theatre, a beautifully restored venue from the early 1900s, hosts a variety of live performances and adds to the town's cultural appeal.

Georgetown

Georgetown is a quaint community of around 7,000 with a rich history. Visitors can take a stroll through the town’s historic district, known as “The Circle,” which includes the grand 1839 courthouse and its much simpler 1793 predecessor. The Circle also hosts Sussex County Return Day, a unique election-themed festival held every two years in November. Meanwhile, an annual event, the Festival Hispano, features Latin-themed food, music, and family-friendly activities that bring the community together. For outdoor activities, Trap Pond State Park is just a short drive away and offers canoeing, kayaking, and birdwatching.

These seven towns showcase Delaware’s rich history, with each offering a unique blend of historic landmarks, natural beauty, and cultural experiences. Whether you are looking to explore historic buildings, enjoy outdoor recreation, or sample local cuisine, these charming old-world towns provide a perfect escape for those wanting to step back in time and experience the true spirit of Delaware. So, whether this will be your first trip to the First State or you have been visiting for many years, add these communities to your Delaware itinerary!