Shops and restaurants around Village of Fenwick, Fenwick Island, Delaware. Image credit Khairil Azhar Junos via Shutterstock

6 of the Most Overlooked Towns in Delaware

Delaware goes by many nicknames. The "First State" comes from the state ratifying its constitution on December 7, 1787. This made them the first American colony to undertake such an action. Another nickname is "The Diamond State." The legend behind this comes from American President Thomas Jefferson. The report states that he referred to the region as the "Jewel among the states," which is certainly true when it comes to the small gems spread across the state.

Visitors and residents alike can look forward to several annual celebrations. The first Saturday in May marks the start of Dover Days, one of the oldest Delaware Celebrations. Another event is the Bethany Beach Boardwalk Arts Festival, where works of over 100 artists are displayed along the boardwalk. The latter days of June also mark the Old Fashioned Ice Cream Festival in New Castle County. The festival features delicious frozen treats, fireworks, and live entertainment.

Come discover Delaware, and experience a region filled with many overlooked adventures and towns.

Delaware City

Delaware City Hotel, in the Delaware City Historic District.
Delaware City Hotel, in the Delaware City Historic District. Image credit: Smallbones, CC0, via Wikimedia Commons

Located in Newcastle County, along the Delaware River, sits Delaware City. The founding of the town dates back to the Newbold Family. The family began creating plans for a future community during the early 19th century. The incorporation of the town occurred in 1851.

Cozy Quarters Farm is a family-operated establishment. The farm has trails for horseback riding, as well as a paid farm experience. Visitors can also buy homemade products from jars of honey, to eggs.

A must-visit attraction, Fort Delaware State Park is a historic local landmark. The structure was first built in the mid-19th century. During the Civil War, Fort Delaware housed Confederate prisoners. Today the location provides visitors a greater understanding of that historic era.

The history of Christ Episcopal Church in Delaware City dates back to 1847. The congregation was first organized in 1848, officiated by Bishop Alfred Lee. By 1849 property was purchased, and the first service in the building happened in 1851. The Church is still active today, with its weekly Sunday service.

If you are in town the first Saturday in October, the Delaware City Day Festivities is a popular event for over 40 years. Its purpose is to celebrate the past, present, and future. The event features many activities, culminating in evening fireworks.

Fenwick Island

The Fenwick Island Lighthouse in Fenwick Island, Delaware.
The Fenwick Island Lighthouse in Fenwick Island, Delaware. Image credit George Sheldon via Shutterstock.com

Fenwick Island sits along Delaware's southern border, within Sussex County. Businessman Thomas Fenwick acquired the land near the start of the 18th century. Following World War II, the island became an ideal vacation setting. In 1953 its incorporation as a town occurred.

A popular attraction, Fenwick Island State Park offers areas for swimming and surfing. The Park measures up to 334 acres of land, and its natural beachside setting attracts many visitors. It also is home to a local population of Ghost Crabs, amongst other wildlife species.

The Fenwick Island Lighthouse sits along the state line between Delaware and Maryland. The Lighthouse construction was completed in 1859. For over a century, it stood as a bright state symbol. Today the 75-foot tall structure is a monument to the story of the town.

While in town, check out Candy Kitchen, a family-owned local store. Operational since 1937, the business has a wide array of delicious concoctions. The list includes saltwater taffy, and a selection of chocolate delicacies.

In addition, Twining's Lobster Shanty provides a comfortable scenic experience and quality food. The list of menu options includes a Shanty House Ruben sandwich and a 2lb Maine Lobster.

Milton

Main street in Milton, Delaware.
Main street in Milton, Delaware. Image credit Khairil Azhar Junos via Shutterstock.com

Milton sits 15 miles northwest of Rehoboth Beach, in Sussex County. The incorporation of Milton as a town occurred in 1865. The inspiration for its name comes from English Poet John Milton.

A statue of Milton sits along the historic "Governor's Walk". A tradition exists within the community of decorating the statue. From Christmas Jackets to springtime flowers, expect the statue in seasonal attire.

The Milton Historical Society Museum teaches visitors the legacy of the town. Within the museum are many historic artifacts. The list includes a printing press from the Milton Publishing Company.

Wagamons Pond is a 44-acre region known for its natural beauty and an ideal spot for fishing. The list of species includes pickerel, largemouth bass, and more. It is a way to spend a relaxing day outdoors.

For those interested in hitting the links, Stenger's Shamrock is the place to go. It is a Par-54 course featuring 18 challenging holes. Another outdoor recreation spot is Milton Memorial Park. Visitors can spend the day walking along trails or relaxing in the picnic area. The Park also hosts the Sounds of Summer Concert Series.

For over a century, Milton Theatre has been a primary source of local entertainment. Visitors can book tickets to a variety of upcoming performances. The schedule includes the University of Delaware Jazz Band.

Millsboro

Waterfront homes near Millsboro, Delaware.
Waterfront homes near Millsboro, Delaware.

Millsboro sits in Sussex County, along the Indian River. The establishment of the community dates back to 1792, with the building of a Grist Mill, and Sawmill. Many famous figures have resided in Millsboro during their lives. The list includes Lulu Merle Johnson. Johnson is the first African American Woman to receive a PH.D. from an Iowa institution.

The Nanticoke Indian Museum tells the story of the Nanticoke Indian tribe. A trip to the museum allows visitors to explore the artifacts and historic exhibits. The adjoining gift shop also provides available memorabilia.

A must-visit business in town, 2nd Time Designs is a family-operated business. Judy and Lou Hagen design the creations that adorn the yard of their household. The unique feature of these creations is that the initial parts come from the local junkyard. One example is the Spinner Flower made out of a recycled bicycle wheel.

Millsboro Pizza Palace serves local residents a great slice of homemade pizza. Visitors can relax and sample from their available menu. The list includes the Large Mega Meat Pizza. It is a great restaurant for the entire family to visit.

For those wanting to play golf, Plantation Lakes Golf Course is the spot for you. Patrons can plan a relaxing day on the 18-hole par 72 course. The nearby Indian River is also an ideal fishing location. The list of species found in the river includes wahoo, striped bass, and Atlantic croaker. In 2020, a 12.69-pound flounder was caught by fishermen in the river.

Cupola Park is a popular local spot, along the Indian River. There are two boat ramps, two picnic pavilions, and a playground. Nearby is WB Atkins Memorial Park, host of the Millsboro Little League. Across their five baseball fields, 44 registered teams take part in America's Pastime.

Georgetown

The Circle, in Georgetown, Delaware houses the Town Hall, the Sussex County Courthouse, and other historic buildings.
The Circle, in Georgetown, Delaware.

Georgetown is within the central region of Sussex County. Today, the town has acclaimed historic sites highlighting its two centuries of existence. It is also a welcoming locale, with fantastic natural scenery.

The Georgetown Circle was established in 1791. The Circle is a National Historic Landmark situated near the Sussex County Courthouse. This unique man-made feature is the location of the Return Day Festival. On Election Day, people venture to the square to hear the results of the voting process. The celebration dates back to the late 18th century.

The Georgetown Speedway is a popular local racetrack. Built in 1949, the half-mile track is home to entertaining stock-racing events. They host annual competitions like the Camp Barnes Benefit Stock Car Race. Renovations recently occurred on the grandstands and parking area.

Back in town, the highlight of the Marvel Carriage Museum is the 30 antique carriages. These carriages were the gift of the Marvel family heirs. The museum also has other historic artifacts from musical instruments to photographs.

Georgetown is also home to the Delaware Aviation Museum. The local building houses displays of vintage military planes. It also serves as an educational exhibit. Inside the museum sits documentation detailing the progress of plane development.

Just outside of town, Mulligan's Pointe is an 18-hole par 72 golf course. It is a peaceful environment, providing an enjoyable day outdoors. The adjoining bar and restaurant also serve as an entertaining atmosphere. Guests can eat great food, and watch live music.

Sports at the Beach is a local activity complex. It hosts over 40 annual youth baseball tournaments across their 16 baseball fields. There are also basketball courts, a swimming pool, and a playground.

Bridgeville

Former Bridgeville Public Library in Bridgeville, now a curio shop.
Former Bridgeville Public Library in Bridgeville, now a curio shop.

Bridgeville sits in the western region of Sussex County, near the Maryland border. The region was first settled by Christopher Nutter in 1684. This occurred following a land grant given by English Statesman Charles Calvert. The incorporation of Bridgeville as a town occurred on March 29, 1871. Today, Bridgeville is a lovely locale, with a wonderful outdoor environment.

October is the time for the Apple Scrapple Festival. The idea for the event occurred as a way to celebrate the local agricultural industry. Festival patrons enjoy live entertainment, as they sample from the food vendors. The 2024 edition takes place October 11th and 12th.

For over 40 years, Jeff's Taproom and Grill has served citizens great food. They offer customers a selection of craft beers. There are also other delicious menu items, such as the bacon hickory cheeseburger.

The Smith family has been growing fresh produce for over a century in the Bridgeville area. In 2017, family descendant Charlie Smith built the Orchard Point Market. Over time, the market became a popular attraction with fruits, vegetables, and pastries. Guests can also meet their goats, with a visit to the adjoining petting zoo.

Antique Alley is a local vintage store. The 20,000 square foot structure is home to 125 booths, and more than 70 shopping ventures. The center houses items ranging from furniture to neon signs.

The state of Delaware is the second smallest in America, ahead of Rhode Island, and is often overlooked when it comes to travel plans. Across its three counties, New Castle, Kent, and Sussex, there are many overlooked towns and plenty of places to explore. From Fenwick Island Lighthouse to the Georgetown Speedway, there is much to discover in the Diamond State! So what are you waiting for? Plan your trip now!

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