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Delaware’s 9 Most Underrated Towns to Visit in 2024

by Staff

On June 15, 1776, Delaware formally declared independence from the British Empire. The newly independent colony played an important role in the following Revolutionary War. It was the evening of December 25th, 1776, when General George Washington crossed the Delaware River to attack a fleet of enemy British vessels. This victory helped to bolster morale in his disenchanted forces and became an inspiring legend in American Folklore.

Delaware is considered the oldest state in the United States. This is due to it being the first state to ratify its constitution on December 7, 1787. Another nickname used to describe Delaware is the Diamond State. This comes from American Founding Father Thomas Jefferson referring to Delaware as a “jewel” amongst the other states.

Though it is a small state, Delaware has been home to many modern-day celebrity figures. The list includes Actress Aubrey Plaza and American President Joe Biden. Delaware is a region replete with beauty and adventure. From the Corbit-Sharp House in Odessa to Battery Park in New Castle, the state is filled with hidden jewels awaiting your exploration. Discover nine underrated cities in Delaware that you will love visiting in 2024.


Aerial view of Lewes, Delaware. Editorial credit: Khairil Azhar Junos /

Lewes is situated within Sussex County, alongside the Delaware Bay. The region was first discovered by sailor Henry Hudson in 1609. Hudson believed the region would be ideal for settling, and by 1631, the oldest settlement in Delaware was established.

Today, Lewes is a lovely coastal town with a well-preserved cultural heritage. One of the places to observe this is the Zwaanendael Museum. The Museum is named after the first European colony in the state “Swanendael.” The colony was settled in 1632 by the Dutch before the British took over the territory. Visitors get to explore the story of Lewes and learn its history.

The Ryves Holt Estate is one of the oldest surviving estates in Delaware. In 1721, Holt purchased the existing estate following his appointment at the Port of Lewes. The property changed hands many times over the years. Eventually, it was purchased by the Lewes Historical Society in 2005.

1812 Memorial Park is a historic local monument. The structure is meant to commemorate the history of Lewes during the War of 1812. From April 6 to 7, 1813, the region faced the brunt of a British attack. Following the attack, cannonballs launched at Lewes would get collected and have been preserved over the centuries.

The ferry from Lewes to Cape May, New Jersey, is a way for visitors to explore the coastal region. The 17-mile journey occurs daily, and visitors can enjoy a lovely scenic journey of historic structures. The place to go for Ice Cream in Lewes is Hopkins Farm Creamery. Open from March to December, the establishment offers over 25 flavors to guests. So come visit and order either a Brownie Cone or Chocolate Banana Walnut.


Cantwell's Tavern in Odessa, Delaware. Editorial credit: Michael G McKinne /
Cantwell’s Tavern in Odessa, Delaware. Editorial credit: Michael G McKinne /

The town of Odessa is situated within New Castle County. By 1731, the region was captured by the British, taking the name Cantwell’s Bridge. As Cantwell’s Bridge, the community was a thriving commercial metropolis for decades. Eventually, as the area developed, the residents chose to rename the community to Odessa. By 1873, Odessa was officially granted a municipal charter.

Centuries later, Odessa is a vibrant community. It has a great culture, plenty of locations for entertainment, and a well-preserved history. The Corbit-Sharp Estate is one of over 80 local historic landmarks. Built-in 1772, the estate was home to Mary and Daniel Corbit, who were abolitionists. Listed as a national landmark in 1967, the house exists today, reflecting the accuracy of the period.

Appoquinimink Friends Meeting House is a local National Historic landmark. Built in 1785 by David Wilson, the house served as a gathering base for the Quaker community in that period. In the years leading up to the Civil War, the property served as a location on the historic Underground Railroad. Following the war, the land would be used by local farmers. The estate was restored to historical accuracy in 1938 and since then has served as a place for worship and meditation.

Odessa Brewfest is a singular-day local event. The event takes place in early September and provides merchandise, food, and live entertainment. The VIP tasting allows certain attendees the chance to taste one of the most highly acclaimed beers in the local region. All funds from the event go to the Historic Odessa Foundation, which helps to preserve local landmarks.

Cantwell’s Tavern is a historic building in Odessa, built as a hotel in 1822. For a century, it served travelers, from merchants to ship captains. In 2011, the property was reopened by the Ashby Hospitality Group. Today, Cantwell’s Tavern is a restaurant offering guests selections from Seared Jerk Duck Breast to Grilled Filet.


Blue pick-up truck on the street in front of the Everett Theatre in Middletown, Delaware. Editorial credit: Alexanderphoto7 /
Blue pick-up truck on the street in front of the Everett Theatre in Middletown, Delaware. Editorial credit: Alexanderphoto7 /

Situated within New Castle County lies Middletown. The community emerged within a region of land purchased by Adam Peterson in 1678. The incorporation of Middletown would occur on February 12, 1861. Upon its incorporation, Middletown was referred to as the “Diamond Town of the Diamond State.” Today, the Middletown community is nationally acclaimed and known for its charming ambiance. The local St. Andrews school and Everett theatre were key settings in the 1989 film Dead Poets Society.

The Everett Theatre is a local landmark. Prior to 1922, two efforts were made to build a theatre in Middletown. The theatre was named after the man responsible for its construction, John Everett Lewis. For decades, the 600-seat theatre entertained residents with motion picture entertainment. For a time, the building fell into disrepair, but the community united to restore the building back to its cultural importance. Today, Everett Theatre is a performing arts center entertaining the masses. It is also a landmark in Hollywood cinema.

There are many events that celebrate local history, one such being the Middletown Incorporation Day Ball. February 12 marks the date of festivities as guests are invited to participate in a period-structured event. The first event occurred in 2011, marking the 150th anniversary of Middletown’s incorporation.

The Olde-Tyme Peach Festival has become a staple local event. It was started in 1993 as a way to symbolize the historic connection the town has with peaches. The event features entertainment for all involved with crafts and competitions. The annual peach parade is what kicks off the festivities.

Coleman’s Christmas Tree Farms is a family-owned business with a history in the region as far back as 1932. The business has grown through the decades, now providing the largest offering of plantation-grown Christmas trees in Delaware. Visitors can also purchase an ice cream treat with flavors like ginger snap and butter pecan.


Boardwalk at Trap Pond State Park.
Boardwalk at Trap Pond State Park.

The town of Laurel is situated within Sussex County. The region was discovered in 1683, and by 1711, it was the home of a Nanticoke Indian Reservation. By 1802, the planning for a new community began, and on April 13, 1883, the incorporation of the new town occurred. Upon its incorporation, Laurel provided avenues for business, with stores, factories, and 2 hotels.

Today, Laurel has developed into a charming river town with its own unique natural beauty. It is also home to the most historic structures of any Delaware town. Guests can learn about this history through a visit to the Laurel Heritage Museum. Located at the former local train station, the museum holds large numbers of documents that tell the story of the region. It also is home to a highly acclaimed Waller Photographic Collection.

The Laurel Historical Society is stationed at the old Cook Estate. It was the home of William and Mollie Cook, who purchased the property in 1909. Today, the property is home to a collection of documents and artifacts that tell the story of the town.

Loblolly Trail is a beautiful walkway highlighted by its scenery. The pathway loops around the local Trap Pond State Park and is traversable through a variety of ways, from mountain biking to running. Roger C Fisher Laurel River Park is another one of the locations for those desiring a day outdoors. Visitors can spend a day boating on the water or relaxing in the lovely picnic pavilion area. There is also a fishing pier and public playground.

On a 25-acre region of Laurel sits the local flea market. Guests can traverse the local shops perusing for available goods. From healthy produce to antique items and clothing, the Laurel Junction Flea Market offers great prices for available items.

Since 2008, Laurel Pizzeria has offered high-quality and affordable food. The highly acclaimed family-owned establishment caters to a variety of experiences, from a family night out to a catered meal. Guests can order from the variety of available delicacies, from a Meat Lovers Pizza to a Cheese Calzone.

The 4th of July is a festive celebration across America, and Laurel is no different. Every year, guests are invited to join the festive spirit with live entertainment, a petting zoo, and food vendors. The celebration culminates with the annual fireworks show.

Dewey Beach

Dewey Beach, Delaware, U.S.A. Editorial credit: Khairil Azhar Junos /
Dewey Beach, Delaware, U.S.A. Editorial credit: Khairil Azhar Junos /

The town of Dewey Beach is situated along the coastline in Sussex County. Situated to the North of Fenwick Island, Dewey Beach has evolved into a popular tourist attraction. The naming of the town was inspired by Admiral George Dewey for his heroics in the Spanish-American War. In 1981, Dewey Beach was officially incorporated as a town.

Over the years, Dewey Beach has evolved into a popular vacation destination with amenities that cater to everyone. One of the popular locations is the Rusty Rudder. A Beachside restaurant, visitors can take in the lovely setting with great food. The menu includes a Fresh Roasted Turkey Sandwich and Steamed Shrimp. The restaurant also hosts weekend live entertainment.

For over 30 years, Gary’s Dewey Beach Bar and Grill has been a staple local restaurant. The establishment offers a great atmosphere, with beers brewed in-house. The menu offers a variety of delicious delicacies, highlighted by their popular Original Turkey Cheese Steak.

The Delmarva Discovery tour bus offers visitors a chance to experience the essential local sites. The bus caters to a wide variety of explorations, from Beer tours to antique tours. It can also be booked for private groups and serve as a self-guided experience. The tours are available 12 months a year.

The Dewey Beer company is a local establishment offering in-house unique cocktails. Those who stop by can sample from their Beer Menu, with options from a Dewey Pale Ale to a selection of Fruit Beers. There is also a food menu, ranging from a House Burger to a Vegan Curry Bowl.

The popular events centre in Dewey Beach is the NorthBeach. The establishment offers live musical entertainment and an enjoyable dining experience. The list of available menu items includes the Jerk Chicken Tacos and an infamous 1/2 pound Impossible Burger.

Lastly, Fifer’s Farm Store and Kitchen pays homage to a family tradition. For over a century, the Fifer Family Farm has provided fresh produce for the local region. Today, visitors can explore the aisles and shop for fresh produce from the Fifer Farm. The store also provides homemade soups and sandwiches.


Historic Old Peoples Bank building at 14 Commerce Street, Harrington, Delaware. Editorial credit: Don Garrard /
Historic Old Peoples Bank building at 14 Commerce Street, Harrington, Delaware. Editorial credit: Don Garrard /

The town of Harrington is situated within Kent County, in Central Delaware. The name drew inspiration from Samuel Maxwell Harrington, a chief justice and state chancellor. By 1869, the incorporation of Harrington officially occurred, and the city borders were defined as a result.

Today, Harrington has evolved into a comfortable, welcoming community with quality schools. The town also provides a variety of amenities that cater to all forms of interest. The staple local attraction is the Harrington Raceway. Operational since the 1940s, Harrington Raceway is one of the oldest racetracks in the country. Visitors can get a day’s worth of entertainment by watching fast-paced harness racing. The adjoining casino also has over 1,300 slot machines and sports betting spots.

Harrington is the host of the annual Delaware State Fair. Every summer, the town invites guests for a period of live entertainment and exciting activities. The first fair was held in July 1920.

Main Street Cafe is a relaxing local restaurant. With locally sourced ingredients, the store offers a variety of delicacies, from a Hamburger Patty Melt to a Tuna Melt. The Messick Agricultural Museum tells the story of agriculture within the region. Visitors can peruse the location and observe the historic antique equipment used by farmers of days past. The Museum is open from Monday to Saturday and encourages self-guided tours.

Established in 1977, the Greater Harrington Historical Society has done work preserving documented local history. Across their 3 locations, thousands of artifacts have been collected, along with 50 cassette recordings of Harrington residents. They have also committed hours of effort in posting the articles from the historic Harrington Journal online.


The welcome sign painted on the building in Milton, Delaware. Editorial credit: Khairil Azhar Junos /
The welcome sign painted on the building in Milton, Delaware. Editorial credit: Khairil Azhar Junos /

Milton is located in the Northeast section of Sussex County, Delaware. In 1807, the community changed its name, inspired by English poet John Milton. By March 17, 1865, the official incorporation of the town occurred, and a government was formed.

Throughout the history of Delaware, five of its former governors have galled Milton their place of birth. Today, visitors to Milton can traverse the loop which honors these historic local residents.

Wagamon’s Pond is a 44-acre body of water known for its scenery. The region has a diverse fish population featuring Largemouth Bass, Pickerel, and Bluegill. In 2016, the largest catch of a Largemouth Bass in Delaware occurred at Wagamons Pond.

For those wishing to hit the links, Shamrock Par 3 Golf Course is the place to visit. The 18-hole par 54 course first opened in July 2003. No matter the skill level, the course allows visitors the ability to spend a great day outdoors.

The Prime Hook National Wildlife Refuge provides shelter to over 400 species. Established in 1963, the over 10,000-acre habitat is named after the local species of purple beach plums. Today, visitors can traverse over six miles of walking trails, providing ideal opportunities for photography.

For over a century, the Milton Theatre has entertained the local residents. Visitors are greeted with snacks, live entertainment, and a relaxing atmosphere. The feature production of March 2024 is “Anything Goes.”

Bethany Beach

Bethany Beach, Delaware, USA. Editorial credit: David Kay /
Bethany Beach, Delaware, USA. Editorial credit: David Kay /

The town of Bethany Beach lies within Sussex County, 11 miles south of Dewey Beach. The community was first settled in 1901 as a campsite for European missionaries. The incorporation of the community would occur in 1909.

Today Bethany Beach is a peaceful locale where visitors can explore the local shops or simply relax in the sun. One of the popular places to enjoy the outdoors is the local boardwalk. Visitors can traverse the 1/2 mile-long territory, taking in the beautiful scenery and warm climate. The Boardwalk also has shops and foot washing stations.

The highly acclaimed Nature Centre in Bethany Beach is a popular local attraction. Visitors can explore 26 acres of land and connect with over 100 species of wildlife.

Over the Summer, Bethany Beach hosts a weekly outdoor Movie Night. Every Monday, people are invited to the Beach, while on Friday, the showcase takes place at the local Bandstand.

The Poseidon Festival is a showcase of entertainment over a multi-day period. Visitors are invited to participate in a variety of activities, from live cultural entertainment to arts and crafts. Educational exhibits are also offered, with an interactive outdoor learning center.

New Castle

Booth House Tavern, New Castle, Delaware.
Booth House Tavern, New Castle, Delaware.

The town of New Castle is located along the coast of Delaware Bay in New Castle County. The region was first settled by the Dutch in 1651. In 1704, New Castle was established as the capital of Delaware following their breaking away from the rule of English Governor William Penn. Following Delaware’s Declaration of Independence from the British in 1776, Delaware was a temporary state capital before Delaware took on that title.

The Historic Court House Museum is one place of significant history. It was here in 1776 when Delaware Representatives commenced a vote of Independence. The Courthouse also heard the voices of prominent abolitionists of that period. In 2003, the structure was designated a National Historic Underground Railroad Site. Today, the Museum remains open and offers guided tours.

Read House and Gardens is another local museum with a detailed history. In 1804, the 14,000-square-foot estate was completed for George Read II (Read’s father was a signee of the Delaware Declaration of Independence). The estate changed hands multiple times following Read’s death before experiencing a revival in the 1920s. Under the influence of Philip and Lydia Laird, the couple revitalized the property, helping it gain national prestige. Today, visitors can explore the property, which is well preserved in its period design, and grasp a sense of the architecture from a bygone era.

Packet Alley is one of the most famous locations in Delaware’s history. Up until the 1840s, New Castle was a frequent travel hub connecting Washington DC with Philadelphia and New York. It was in Packet Alley, where stagecoaches would unload the luggage of their passengers before placing them on the boats. Today, the Alley is signified by a historic monument. Here, visitors can step in the same spots as historical figures like American President Andrew Jackson and Davey Crockett.

New Castle also has beautiful outdoor features, highlighted by Battery Park. The region provides miles of trails for exploration of the nearby Delaware River. It also has other amenities, such as picnic spots and volleyball courts.

The Separation Day festivities in New Castle are one of the longest continually run traditions in Delaware. Every June, the town offers live entertainment, from Music, Fireworks, and a Parade. June 7th & June 8th, 2024, will mark the 248th edition of the Separation Day Festivities.

The state of Delaware is replete with ways to create lifelong memories. There are festivals in New Castle and Odessa, as well as historic buildings in Lewes and Harrington. And that is just a taste of what this region has to offer. Whether exploring the quaint streets of Lewes, marveling at the historic landmarks in Odessa, or enjoying the coastal beauty of Dewey Beach, Delaware offers endless possibilities for adventure and discovery. So stop what you are doing right now and plan your next visit to discover the charm and allure of the First State.

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