Historic buildings on Main Street, Odessa, Delaware.

7 Unforgettable Small Towns To Visit In Delaware

Delaware, known as "The First State" because it was the first of the original colonies to ratify the 1787 Constitution, holds a rich historical legacy within its Atlantic Coastal Plain setting. It stretches along the northeastern shores of the country, offering a diverse range of landscapes and the charming appeal of small towns. The state derives its name from Delaware Bay, which borders it and boasts a host of popular beaches along its coastline. However, Delaware's lesser-known picturesque towns and villages best showcase its historical and cultural heritage. From quaint riverfront settlements to historic districts that transport you back in time, Delaware offers a wealth of experiences for travelers seeking an unforgettable trip.

Odessa

The historic Odessa Bank on Main Street, Odessa, Delaware.
The historic Odessa Bank on Main Street, Odessa, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

Odessa, an 18th-century village, preserves its rich historical and cultural heritage. To explore the town's roots, visitors should head to Odessa's Historic District, where they will encounter a collection of historic buildings with pleasing architectural styles. In this district, a visit to 18th-century landmarks such as the Corbit–Sharp and Wilson-Warner Houses provides valuable insights into the late 18th and early 19th-century lifestyles through historic furnishings.

Nature enthusiasts will delight in knowing that the town is very close to the Blackbird Creek Reserve, which features numerous walking trails through woods, fields, and riverbanks, offering a wholesome outdoor experience. The Appoquinimink River, which flows nearby, provides further opportunities for enjoying nature, including kayaking, canoeing, and other boating activities. For those visiting during the spooky season, a must-stop is The Frightland theme park, one of the nation's top haunted houses, where you can immerse yourself in various horror-themed attractions, carnival games, and hayrides.

New Castle

A beautiful historical building in New Castle, Delaware.
A beautiful historical building in New Castle, Delaware. Editorial credit: Joseph Sohm / Shutterstock.com

New Castle, a unique city situated on the Delaware River and the oldest continuously occupied city in the state, boasts a rich history at every turn. Visitors can explore this history by taking a guided walking tour of the city and visiting notable sites like the New Castle Court House Museum, the Lesley-Travers Mansion, and the Amstel House. Walking through the cobblestone paths and admiring the age-old architecture will transport you to another era.

To soak in the beauty of New Castle, head to Battery Park on the Delaware River. The park offers playgrounds and tennis courts for visitors to enjoy, and the Battery Park Trail provides breathtaking waterfront views for those on foot. The park's greenery also makes it an ideal picnic spot. In the evening, indulge in mouth-watering local dishes at Jessop's Tavern and Colonial Restaurant, a pub established in 1724.

Delaware City

Fort Delaware, a historical attraction near Delaware City, Delaware.
Fort Delaware, a historical attraction near Delaware City, Delaware.

Delaware City, a charming riverside town situated along the Delaware Canal and Chesapeake Bay, offers a wholesome getaway for travelers. History enthusiasts should not miss Fort Delaware, situated on Pea Patch Island. The fort provides an unforgettable historical experience with costumed interpreters who transport you back in time, narrating the battles and history of the site. Lucky tourists may even witness occasional reenactments of battles within the fort.

Fall is an ideal time to visit Delaware City, as it offers popular spooky season activities, including ghost tours and paranormal investigations in Fort Delaware for the adventurous. In the summer, the waters surrounding the city become perfect spots for boating, fishing, and cruises. The town hosts various seasonal festivals throughout the year, including the Festival of Trees, which visitors may be fortunate enough to experience.

Laurel

Chipman Pond, Laurel, DE
Chipman Pond, Laurel, Delaware. Image credit: Lee Cannon via Flickr.com

A historic town surrounded by numerous parks and ponds, Laurel offers mesmerizing natural beauty throughout the year. The Roger C. Fisher Laurel River Park and Trap Pond State Park are delightful spots for picnics and outdoor activities such as hiking, biking, and running. Both these parks also feature river bodies where people are often found boating and fishing. To explore some of the famous ponds, tourists can visit Horseys Pond or Laurel Lake.

Like many other Delaware towns, Laurel boasts a rich history, with 800 buildings on the National Register of Historic Places, making it the state's largest collection of historic sites. The Laurel Heritage Museum is an ideal place to gain a detailed understanding of the town's history. Notable sites to visit include the Sussex Trust Building, the Laurel Railroad Station, and the Cook House Museum, which can be explored through comprehensive guided tours of the town's historic district. The summer months are a perfect time to visit Laurel, with blooming nature and various activities, including family movie nights and Lakefest.

Smyrna

South Main Street in Smyrna, Delaware
South Main Street in Smyrna, Delaware. Image credit: Dough4872 via Wikimedia Commons.

Smyrna, another small town steeped in history, is a quaint city situated on the western banks of the Delaware River. The downtown area features approximately 850 residential, commercial, and historic buildings dating back to the 18th and 19th centuries. The Smyrna Museum, housed in two wartime buildings from the 1700s, displays Smyrna's three centuries of existence with numerous historical exhibits, including documents, garments, paintings, and other artifacts. Another historical gem is the Belmont Hall, famous for its 18th-century architecture and beautiful surrounding gardens.

However, Smyrna is also quite famous for its artistic and creative atmosphere. The century-old Smyrna Opera House hosts multiple musical, theatrical, cultural, and visual performances, making it a must-visit during your trip. Considering how popular Smyrna's distilleries are, it would be a shame to leave without taking the Painted Stave Distilling tour. For tourists who want to add a nature-filled day to their itinerary, head to the Bombay Hook National Wildlife Refuge for a unique wildlife experience or explore picturesque walking and hiking trails in the Blackbird State Forest.

Milford

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

Milford is a cozy town nestled along the banks of the Mispillion River that exudes a homely vibe. The town often attracts artists and creatives due to its numerous cultural centers and regular festivals. Popular festivals include the Bug & Bud Festival, Riverwalk Freedom Festival, and Ladybug Music Festival, typically held later in the summer, making August and September ideal months to visit Milford. The Riverfront Theatre is a great place to catch local performances, while the Mispillion Art League hosts artistic exhibits.

Milford is renowned for its hole-in-the-wall eateries, including My Sister's Fault, which offers a local twist on Mexican cuisine and is a must-try. You can also get a taste of local beers and spirits at the Mispillion River Brewing and easySpeak Spirits. In the evening, take a peaceful stroll along the waterfront at the Downtown Riverwalk or explore local art projects on display during the Milford Art Stroll.

Frederica

House in the Frederica Historic District.
A beautiful house in the Frederica Historic District. Image credit: Smallbones via Wikimedia Commons.

Known as "Frogtown" due to its proximity to water bodies, Frederica is the go-to small town for those seeking a relaxing vacation spot in Delaware. This village, once a former port site, has evolved into a charming town with scenic views and a warm, quiet ambiance. Tourists often visit the Killens Pond State Park, where they can enjoy paddle boating, canoeing, or kayaking, hike the trails, and discover live animals in the nature center. The park also includes the Killens Pond Water Park, where children and adults can both enjoy cooling off.

For another fun family day, Bowers Beach, which is close to Frederica, is the ideal spot to lay back, sunbathe, and spend a relaxing afternoon. Anyone interested in seeing the historical aspect of the town should visit Barratt's Chapel, which is claimed to be one of the most important Methodist historical structures in the State. It would be wise to avoid Frederica in peak summer because of the slightly uncomfortable smell that graces the atmosphere due to the nearby marshes, but at all other times of the year, this town is very welcoming. 

In conclusion, Delaware offers a treasure trove of experiences for travelers in search of both natural beauty and rich cultural heritage. From the captivating 18th-century charm of Odessa and the historic streets of New Castle to the artistic atmosphere of Smyrna and the creative hub of Milford, the state offers a host of experiences to suit every traveler's unique needs. Delaware is a state that has preserved its history, embraced its natural beauty, and embodied a creative spirit, beckoning visitors with open arms. So, for those planning their next adventure, consider venturing beyond the well-known cities to discover the hidden treasures that make Delaware an unforgettable destination.

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