The seaside town of Rehoboth Beach, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com.

9 Underrated Small Towns To Explore In Delaware

Delaware, “The First State” among the Thirteen Colonies to formally validate the US Constitution on December 7, 1787, is an incredibly beautiful state occupying the Delmarva Peninsula’s northeastern part in the United States’ Mid-Atlantic region. With the advent and exploration by Europeans, the ‘Blue-Hen State’ gradually developed over the years to become one of the most sought-after holiday destinations on the East Coast. Even though Dover - the state capital, and Wilmington - the largest city, get the maximum tourist attention, the innumerable underrated small towns sprinkled all over the varied landscapes of ‘The Diamond State’ are sublime locales for spending your holidays and making long-lasting memories with near and dear ones.

Milton

A view of the town of Milton, Delaware
A view of the town of Milton, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com.

Milton, christened after the eminent English poet John Milton, is an enchanting Sussex County town situated at the headwaters of the Broadkill River on the Delmarva Peninsula in Southern Delaware’s burgeoning Cape Henlopen Region. Aside from its protective small-town allure, the town pridefully holds on to its rich maritime legacy thanks to its placement close to Delaware Bay. A significant portion of Milton’s central business district and adjacent residential areas is encompassed by the National Register-listed Milton Historic District, which includes some of the most magnificent Victorian and Colonial properties. The Lydia Black Cannon Museum, Title & Safe Deposit Company Building, Milton Theater, Gov. James Ponder House, Draper-Adkins House, and Governor David Hazzard Mansion are must-visit sites of interest. The Dogfish Head Craft Brewery is ideal for those who wish to taste craft beers, while the Prime Hook National Wildlife Refuge and the Milton Memorial Park are must-stops for all nature enthusiasts.

Odessa

Main Street in Odessa, Delaware
Historic buildings on Main Street in Odessa, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com.

Primarily settled in the 18th century and called ‘Cantwell’s Bridge,’ this charming New Castle County town alongside the Appoquinimink River has been relabeled after its namesake Ukrainian port city. Much of this only 366-resident town forms a part of the Odessa Historic District which comprises a number of meticulously maintained landmark structures such as the Corbit-Sharp House, Old St. Paul’s Methodist Episcopal Church, Appoquinimink Friends Meetinghouse, Collins-Sharp House, Wilson-Warner House, and many more. Rest your feet after a hectic day of touring at the cozy Cantwell’s Tavern restaurant, besides savoring its mouthwatering regional dishes, craft beer, and cocktails. Annually, thousands flock here to partake in the Christmas in Odessa festivities and Historic Odessa Brewfest.

Bethany Beach

Drone photo of Bethany Beach Delaware
Drone photo of Bethany Beach, Delaware.

An enthralling Sussex County community, Bethany Beach, situated betwixt the Miller Creek and Indian River Bay, is bordered by the Atlantic Ocean to the east, the town of Ocean View to the west, Delaware Seashore State Park and Salt Pond to the north, and South Bethany to the south. Sometimes dubbed “The Quiet Resorts,” in addition to the contiguous coastal settlements of Fenwick Island and South Bethany, the town, with its unhindered beach access, is a peaceful retreat for inhabitants of other adjoining congested towns. Browse the numerous downtown antique stores, souvenir shops, motels, accommodations like Bethany Beach Ocean Suites Residence Inn, and seafood restaurants like Off The Hook, apart from participating in different activities on the public beaches. Also, enjoy mind-boggling sunset and sunrise views from the Bethany Beach Boardwalk, or take a jaunt to the close by Bethany Beach Nature Center and Fenwick Island Lighthouse.

New Castle

New Castle, Delaware
Row homes with American flags in the historic New Castle, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com.

Located approx. 6 miles south of Wilmington, this teeny town in New Castle County by the side of the Delaware River forms a portion of the Delaware Valley metropolitan region. Set up in 1651 by the Dutch West India Company under the headship of Peter Stuyvesant, New Castle is Delaware’s oldest continuously inhabited settlement. Discover the uncountable well-maintained structures from the 17th to early 19th centuries lining the New Castle Historic District’s cobblestone streets and the town’s other noteworthy sites of interest such as the New Castle Court House Museum, Old Dutch House, Amstel House Museum & Gardens, Immanuel on the Green, and Read House & Gardens. Unwind after an eventful day by relishing Andouille meatloaf and lip-smacking colonial-inspired dishes at Nora Lee’s French Quarter Bistro and Jessop’s Tavern.

Delaware City

 Delaware City, Delaware
A historical building in Delaware City, Delaware. Image credit: Bernt Rostad via Flickr.com.

This attractive coastal town, situated on the Chesapeake & Delaware Canal’s eastern end in New Castle County, acts as an entranceway to the settlement’s other natural and historical treasures. While on a visit to Delaware City, architecture fanatics should take a ferry to Pea Patch Island and inspect the five-sided Fort Delaware in Fort Delaware State Park, looking out on the Delaware River. Also, visitors must not miss the Diamond State Base Ball Club’s home field at the adjoining Fort DuPont State Park and the more than 204 buildings in Greek Revival and Italianate styles in the Delaware City Historic District. Additionally, ample recreation can be availed by adventurous types at Battery Park, Dragon Run Park, Bubby Sadler ballfields, Seventh Street Park, Community Center grounds, and Dragon Run Park.

Lewes

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

Affectionately called “The First Town In The First State,” Lewes occupies the mouth of Delaware Bay within the Salisbury, MD-DE Metropolitan Statistical Area in Sussex County of southeastern Delaware. Nestled betwixt the immaculate beaches of Cape Henlopen State Park and the wetlands of Great Marsh Preserve, this laid-back seaside community is jam-packed with fully renovated properties, including the Ryves Holt House, Lewes Presbyterian Church, William Russell House, etc. Moreover, the visitors can get an insight into the area’s bygone days at the Zwaanendael Museum and the Fort Miles Museum & Historic Area. Set out on a shopping spree and browse the countless antique shops, souvenir stores, confectionaries, eateries that satisfy any palate, and breweries in Lewes’s walkable downtown. Outdoorsy types must visit the Cape Henlopen State Park to take part in plenty of recreational activities, traverse the Gordons Pond Trail winding through the state park’s varied ecosystems, and witness jaw-dropping sunsets.

Hockessin

Mt. Cuba Center, Hockessin, Delaware
Blooming white tree at the Mt. Cuba Center, Hockessin, Delaware.

Hockessin, first settled by a group of families in 1688 on Mill Creek’s eastern shores, is situated in New Castle County near the state’s northwestern boundary within 1.2 miles of the Delaware-Pennsylvania border. Travelers visiting this typical ‘commuter town’ must gaze in wonder at the various landmark properties like the Hockessin Friends Meetinghouse, Springer Farm, T. Pierson Farm, and Lamborn Library (Public School No. 29) while on a drive through Hockessin’s neighborhoods. Riders can embark on a round-trip from Hockessin to Greenbank Station via the historic Wilmington & Western Railroad that runs through the Red Clay Creek valley. The Ashland Nature Center is an out-and-out butterfly-watching place during the summer and spring seasons, whereas the several miles of walking paths and vast playground of the Swift Memorial Park are ideal for spending great moments with loved ones.

Rehoboth Beach

Rehoboth Beach, Delaware.
The charming beachside scene of Rehoboth Beach, Delaware. Editorial credit: Foolish Productions / Shutterstock.com.

One of the leading towns of the booming Cape Region, Rehoboth Beach is a sought-after affluent holiday haven in the eastern portion of Sussex County adjacent to the Delaware Beaches. Holidaymakers visiting “The Nation’s Summer Capital” can enjoy an outstanding seaside vacation complete with ultra-clean beaches, boutiques, walking trails, art galleries, home-like accommodations, entertainment venues, diners, amusement parks (Funland), and the Rehoboth Beach Boardwalk. Stop by the Anna Hazard and Rehoboth Beach Museums and take note of their displayed period exhibits telling tales about regional history. Aside from the incredible beaches, the town has a few open spaces such as Grove Park, Martin’s Lawn, Stockley Street Park, Lee Street Park, Teardrop Park, Deer Park, and Lake Gerar Park. The yearly Rehoboth Beach Independent Film Festival, Rehoboth Beach Autumn Jazz Festival, and Sea Witch Festival lure hundreds of merrymakers to Rehoboth Beach.

Millsboro

Millsboro, Delaware
The aerial view of the waterfront homes with a private dock near Millsboro, Delaware.

Forming a portion of the Salisbury, MD Metropolitan Statistical Area, this delightful Sussex County town is around half an hour's drive from Bethany Beach. Having an inviting downtown area and a slower pace of life, Millsboro is a quintessential settlement to stay in Southern Delaware. This 6,863-inhabitant waterfront community is home to many notable sites, including the Issac Harmon Farmhouse, Indian River Archeological Complex, Indian Mission Church, Harmony Church, and Nanticoke Indian Museum. Furthermore, the town’s placement by the headwaters of the Indian River has made it an ideal place for adventurists wishing to participate in water-based recreations like fishing, boating, crabbing, swimming, etc. Browse the Washington and Main Streets crammed with numerous finest restaurants offering first-class dining options.

From the beautiful beaches of Bethany Beach to Lewes - “The First Town In The First State,” each pretty hamlet in the 2nd smallest and 6th least populous state of the nation mesmerizes tourists with their uniqueness. So, if you are on the lookout for locales having several miles of undefiled yellow-sand beaches, arresting state parks & wildlife refuges, lovely colonial homes, and infinite recreational opportunities, look no further than these picture-perfect towns for a rememberable Delawarian experience.

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