Canalfront Park in Lewes, Delaware.

10 Picture-Perfect Towns In Delaware

Bounded by the Atlantic Ocean in the east and by the US States of New Jersey, Pennsylvania, and Maryland in the northeast, north, south, and west respectively, Delaware is a picturesque state in the Mid-Atlantic region of the United States. Affectionately called the “First State” for being the foremost among the original Thirteen Colonies to ratify the US Constitution, Delaware has gradually transformed over the years to become one of the favored tourist destinations on the nation’s East Coast. Although the state capital Dover and the most populous city Wilmington are most preferred by vacationers, the innumerable picture-perfect towns that dot the state, entice tourists with their miles of pristine golden-sand beaches, stunning state parks & wildlife refuges, charming colonial homes, and limitless outdoor recreation.

New Castle

Aerial view of the sunny beach in New Castle, Delaware.
Aerial view of the sunny beach in New Castle, Delaware.

A part of the Delaware Valley metropolitan region, this small town in New Castle County is located along the Delaware River, around 6 miles south of Wilmington. Initially settled in 1651 by the Dutch West India Company under the leadership of the Dutch colonial officer Peter Stuyvesant, New Castle is the state’s oldest continually inhabited settlement. Tourists visiting the town must stroll down the cobblestone streets of the National Register-listed New Castle Historic District and discover the countless carefully maintained landmark structures dating from the 17th to the early 19th centuries. New Castle’s notable sites of interest include the New Castle Court House Museum (included within the First State National Historical Park), Amstel House Museum & Gardens, Read House & Gardens, Immanuel on the Green (Episcopal Church), and Old Dutch House. After exploring these historic sites, taste the delicious colonial-inspired dishes at Jessop’s Tavern and Andouille meatloaf at Nora Lee’s French Quarter Bistro.

Smyrna

The beautiful scenery of the Bombay Hook National Wildlife Refuge, in Kent County, Smyrna, Delaware.
The beautiful scenery of the Bombay Hook National Wildlife Refuge, in Kent County, Smyrna, Delaware.

Spread across the Kent and New Castle counties in the south-central portion of the state, Smyrna forms a part of the Dover Metropolitan Statistical Area. Originally referred to as “Duck Creek Cross Roads,” the town was renamed in 1806 after a former Greek seaport city in Turkey. Home to 12,883 inhabitants as per the latest US Census, Smyrna draws visitors to soak in its small-town charm and gaze in awe at its many well-preserved historic buildings. The Belmont Hall, Cummins-Stockly House, Irishtown Tavern, Alexander Griswold Cummins, Sr. House, Asbury United Methodist Church, Smyrna Museum, and Smyrna Opera House are the town’s noteworthy attractions. The adjacent Bombay Hook National Wildlife Refuge and the scenic Lake Como are preferred destinations for an array of outdoor recreations.

Lewes

The charming town of Lewes, Delaware.
The charming town of Lewes, Delaware.

Nicknamed, “The First Town In The First State,” Lewes is located at the mouth of Delaware Bay in Southeastern Delaware’s Sussex County, within the Salisbury, MD-DE Metropolitan Statistical Area. Nestled between the wetlands of the Great Marsh Preserve and the spotless beaches of Cape Henlopen State Park, this laid-back coastal community is filled with meticulously restored properties including the Ryves Holt House, William Russell House (Russell Farmhouse), Lewes Presbyterian Church, etc. Additionally, the Zwaanendael Museum and the Fort Miles Museum & Historic Area offer visitors an insight into the area’s glorious past. Spend a day in this completely walkable town by browsing the antique shops, museums, souvenir stores, restaurants, confectioneries, and breweries that line the downtown. Outdoor enthusiasts can head to the Cape Henlopen State Park for ample family-friendly recreation, breathtaking sunsets, and biking the 3.2-mile-long Gordons Pond Trail that meanders through the park’s various ecosystems.

Milton

A street in Milton, Delaware.
A street in Milton, Delaware.

Christened by the Delaware Legislature in 1807 in honor of the renowned English poet John Milton, this adorable town forms a part of the flourishing Cape Region at the head of the estuarial Broadkill River in Southern Delaware’s Sussex County. Thanks to the town’s riverside setting and proximity to Delaware Bay, Milton proudly upholds its rich shipbuilding heritage besides its protective small-town charm. Listed on the National Register of Historic Places, the Milton Historic District encompasses much of the town’s central business district and adjoining residential areas and includes some of the state’s finest Victorian and Colonial architecture. The Lydia Black Cannon Museum, Milton Theater, Gov. James Ponder House, Governor David Hazzard Mansion, Draper-Adkins House, Governor James Carey home, and the Former Sussex Trust, Title and Safe Deposit Company building are Milton’s prominent historical points of interest. The Dogfish Head Craft Brewery attracts many wine aficionados to taste its popular craft beers, while the Milton Memorial Park and Prime Hook National Wildlife Refuge are must-stops for nature lovers.

Bethany Beach

Beautiful waterfront homes by the bay near Bethany Beach, Delaware
Beautiful waterfront homes by the bay near Bethany Beach, Delaware.

Located between the Indian River Bay and Miller Creek, this Sussex County town is bounded by the Atlantic Ocean to the east, Salt Pond and Delaware Seashore State Park to the north, the town of Ocean View to the west, and South Bethany to the south. Often nicknamed “The Quiet Resorts” alongside the neighboring coastal communities of South Bethany and Fenwick Island, Bethany Beach with its unrestricted beach access, serves as a tranquil retreat for residents of other nearby bustling towns. Aside from enjoying the numerous activities on the town’s public beaches, travelers must also check out the various antique shops, souvenir stores, vacation homes, motels, and seafood restaurants in downtown. Moreover, one can enjoy stunning views of sunrise and sunsets from the Bethany Beach Boardwalk, or take a day trip to the nearby Fenwick Island Lighthouse and Bethany Beach Nature Center.  

Millsboro

The aerial view of the residential area and waterfront homes near Millsboro, Delaware
Aerial view of Millsboro, Delaware.

Millsboro, located only half an hour by car from Bethany Beach in Sussex County forms a part of the Salisbury, MD-DE Metropolitan Statistical Area. With a charming downtown area and a relaxed, slower pace of life, this 6,863-inhabitant town is an ideal place to reside in Southern Delaware. Millsboro is home to several National Register-listed sites including the Issac Harmon Farmhouse, Harmony Church, Indian Mission Church, Indian River Archeological Complex, Nanticoke Indian Museum, and Millsboro Arts League. The town’s location along the Indian River makes it a great place for enjoying water-based recreation activities like fishing, boating, and swimming. For excellent dining options, head to the Washington and Main Streets packed with an array of fine sit-down restaurants.

Rehoboth Beach

The view of the luxury waterfront homes by the bay near Rehoboth Beach, Delaware
The view of the luxury waterfront homes by the bay near Rehoboth Beach, Delaware.

One of the Cape Region’s principal towns, Rehoboth Beach is a well-known affluent vacation destination along Delaware Beaches in the eastern part of Sussex County. Travelers can enjoy a superb beach holiday at “The Nation’s Summer Capital,” complete with immaculate beaches, amusement parks, entertainment venues, walking trails, boutique shops, art galleries, eateries, and a 1-mile-long wooden Rehoboth Beach Boardwalk. To learn more about the area’s local history, check out the various period exhibits at the Rehoboth Beach Museum and the Anna Hazard Museum. In addition to beaches, Rehoboth Beach has several open spaces such as Grove Park, Stockley Street Park, Teardrop Park, Lake Gerar Park, Deer Park, Lee Street Park, and Martin’s Lawn. The town also hosts various annual festivals like the Rehoboth Beach Independent Film Festival, the Sea Witch Festival, and the Rehoboth Beach Autumn Jazz Festival.

Odessa

The view of the historic buildings on Main Street
The view of the historic buildings on Main Street, Delaware. Editorial credit: Khairil Azhar Junos / Shutterstock.com

Initially established as Cantwell’s Bridge in the 18th century, this New Castle County town along the Appoquinimink River, has been renamed after its namesake port city in Ukraine. Home to only 366 residents, a significant portion of the town (including its central business district and abutting residential areas) forms a part of the Odessa Historic District, which contains several painstakingly maintained contributing properties like the Corbit-Sharp House, Appoquinimink Friends Meetinghouse, Wilson-Warner House, Collins-Sharp House, Old St. Paul’s Methodist Episcopal Church, Academy building, etc. The town’s Cantwell’s Tavern restaurant serves gourmets lip-smacking farm-to-table cuisines besides craft beer and cocktails. Merrymakers flock to the town every year to participate in the Historic Odessa Brewfest and the Christmas in Odessa festivities.  

Delaware City

Exterior of The Old Canal Shops at 129 Clinton St, Delaware City. 
Exterior of The Old Canal Shops at 129 Clinton St, Delaware City. 

This tiny riverfront community situated in New Castle County on the eastern end of the Chesapeake & Delaware Canal serves as a gateway to the town’s other historical and natural treasures. Architecture buffs must take a ferry to Pea Patch Island and tour the pentagon-shaped Fort Delaware overlooking the Delaware River in Fort Delaware State Park. The nearby Fort DuPont State Park offers visitors opportunities to discover the home field of the vintage Diamond State Base Ball Club. The Delaware City Historic District comprises over 204 buildings built in Italianate and Greek Revival architectural styles, in addition to numerous shops and restaurants. The town’s Battery Park, Seventh Street Park, Dragon Run Park, the Community Center grounds, and the Bubby Sadler ballfields offer abundant recreation activities.

Hockessin

Ashland Covered Bridge, Hockessin, Delaware.
Ashland Covered Bridge, Hockessin, Delaware. Image credit: Chris Foster via Flickr.com

Founded by a group of families in 1688 on the eastern banks of Mill Creek, Hockessin is located close to Delaware’s northwestern border in New Castle County, within 1.2 mi of the state boundary with Pennsylvania. Visitors must take a drive through Hockessin’s neighborhoods and observe the several landmark properties including the Hockessin Friends Meetinghouse, T. Pierson Farm, Lamborn Library (Public School No. 29), Springer Farm, etc. The heritage Wilmington and Western Railroad that runs through the Red Clay Creek valley carries riders on a round-trip from Hockessin to the Greenbank Station. The town also lures nature lovers to its Ashland Nature Center, considered the best place to watch butterflies during spring and summer. The Swift Memorial Park with its massive playground and miles of walking paths is perfect for spending quality time with dear ones.

From the cobblestone streets of New Castle to the exquisite beaches of Bethany Beach, each town in the country’s 2nd smallest and 6th least populous state captivates thousands of holidaymakers with their distinctive charms, along with providing a unique insight into the state’s rich heritage. So, if you want to have an unforgettable Delawarian experience, look no further than these treasured gems of the Diamond State.

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