Dewey Beach, Delaware, Pedestrians crossing the road in the summer.

11 Nicest Small Towns In Delaware

Delaware's best small towns aren't about tourist fanfare or cookie-cutter charm found in many places in the United States. They're real places with streets lined with historic homes, bustling weekend markets, and unexpected character. It's where community still means something and everyday life unfolds with a blend of warmth and a little bit of grit. It's true, you may find some of these towns on a few glossy travel lists. But not the kind that the average tourist checks out. Whether you've heard of these towns or not, they all have a common thread... they're insanely beautiful. Not just in terms of their natural landscapes, but in the attractions they showcase and the history that built them.

Bethany Beach

Bethany Beach, Delaware. (Image credit David Kay via Shutterstock.)
Bethany Beach, Delaware. (Image credit David Kay via Shutterstock.)

Bethany Beach knows exactly what kind of town it is and doesn't overcomplicate things. You like to swim? You like the beach? It's got you covered. This southern Delaware town delivers Atlantic-front beaches without the boardwalk chaos of larger coastal spots. Bethany Beach's half-mile wooden boardwalk is modest. You won't find neon signs or absurd amounts of noise here, just local restaurants, swimmers headed for the surf, and a ton of joggers. Mere steps off the boardwalk, along North and South Atlantic Avenue, and the surrounding downtown streets, you'll find everything from saltwater taffy to arcade games at Shore Fun Family Center. On the quieter side, the Bethany Beach Nature Center borders marshland and gives tourists and residents alike ample opportunity to explore wildlife via walks on the Baldwin Trail.

New Castle

 Rustic buildings in the town of New Castle, Delaware.
Rustic buildings in the town of New Castle, Delaware. Image credit George Wirt via Shutterstock

The riverfront town of New Castle isn't a place where modern reinvention is a priority. It's a rare pocket of the Mid-Atlantic where centuries of history still shape the streets. In the New Castle Historic District, 18th-century rowhouses, cobblestone corners, and buildings like the 1732 Court House and the Dutch House Museum form a grid so well-resevered, it feels like stepping into another time. Locals fill the tavern booths at Jessop's, a colonial-style staple that keeps things hearty and grounded. But while history is plentiful in this Delaware town, its natural beauty demands equal attention. Battery Park, which connects to the Jack A. Markell Trail, wraps along the Delaware River with open lawns, walking paths, and the best views in town.

Rehoboth Beach

Sunrise on the boardwalk in Rehoboth Beach, Delaware.
Sunrise on the boardwalk in Rehoboth Beach, Delaware. Editorial credit: Michelangelo DeSantis / Shutterstock.com.

The town of Rehoboth Beach features a mile-long traditional wooden boardwalk with shops, arcades, ice cream shops, the Funland Amusement Park, and Grotto Pizza stalls. At its heart, the Bandstand delivers over 40 free open-air concerts every summer, Friday through Sunday. It's this attraction, as well as the beach the town shares a name with, that draws tourists each year. Though Rehoboth Beach isn't exclusively beautiful during the summer months. Though it does proclaim itself to be "the Nation's Summer Capital," year-round visitors can slip into Lake Gerar Park and enjoy the quiet waterfront trails lining the inland lake. And not far away, the Rehoboth Beach Museum preserves the town's early years and delves into its unique origin.

Lewes

View of downtown Lewes, Delaware.
View of downtown Lewes, Delaware.

Lewes, "The First Town in the First State", was founded as the Dutch colony Zwaanendael in 1631. Its well-preserved historic district offers treasures like the gingerbread-style Zwaanendael Museum and the stately Ryves Holt House, Delaware's oldest building on its original foundation. The walkable downtown is filled with everything a small town should have. Yes, there are antique shops and boutiques, and even a bookstore. But it's the quality and style of these unfussy places that make them special. Just blocks away from the core of Lewes, Second Street, the town opens up to salt marshes and wide beach views. Locals bike straight from town to Cape Henlopen State Park. It's here where you'll find trails past WWII observation towers, a fishing pier, and the magnificent Cape Henlopen State Beach.

Middletown

Dog Town Restaurant in Middletown, Delaware.
Dog Town Restaurant in Middletown, Delaware. Image credit Alexanderphoto7 via Shutterstock

Middletown once moved peaches by railcar in pre-Civil War Delaware. Today, it moves people, by the thousands, to its annual Olde-Tyme Peach Festival every August, when Main Street shuts down for live music, pie contests, and a peach parade that runs straight through the heart of town. But this place isn't just an attraction in the summer. Though Silver Lake Park, just a few blocks off the commercial strip, is particularly nice on a warm day. With its surrounding farmland, restaurants, and shopping, and nearby Coleman's Christmas Tree Farm, Middletown is one of the most desirable year-round vacation spots in southern New Castle County. It's also home to some pretty iconic buildings, such as The Everett Theatre, which dates back to 1922 and is famous for appearing in Dead Poets Society.

Smyrna

 Boardwalk at the Bombay Hook National Wildlife Refuge in Smyrna, Delaware.
Boardwalk at the Bombay Hook National Wildlife Refuge in Smyrna, Delaware.

Smyrna sits between cornfields and commuter highways, halfway between Dover and Wilmington, but it's never felt like a halfway place. Downtown is compact, a few blocks of brick-front shops and restaurants like Brick Works Brewing and Eats. Though arguably, the most famous place to grab a bite is Helen's Sausage House just off the highway, as the popular truck stop diner has become somewhat of a Delaware legend. In Summer, the man-made Lake Como, which sits right in town, is a popular swimming spot and is used just as much for fishing. And while it's outside of town, Bombay Hook National Wildlife Refuge is a must-see. It's a vast salt marsh where birds gather by the thousands, and the sky stretches flat and low like a lid.

Milton

Outdoor vendors on the street in Milton, Delaware.
Outdoor vendors on the street in Milton, Delaware. (Editorial credit: Khairil Azhar Junos / Shutterstock.com.)

Tucked at the head of the Broadkill River, about 15 miles northwest of Rehoboth Beach, Milton still carries the imprint of its shipbuilding past. That energy is best felt around the historic district's Victorian homes and the riverside footpaths of Milton Memorial Park. The town's best-known 'resident' is arguably Dogfish Head Craft Brewery, which draws steady crowds for its small-batch beers, wood-fired pizzas, and offbeat tours. A few blocks away, the restored Milton Theatre packs the calendar with everything from film nights to burlesque. Just over the river is the Edward H. McCabe Preserve, a forested stretch with trails and river access for those who need a little less beer and a little more nature.

Dewey Beach

Aerial view of Dewey Beach, Delaware.
Aerial view of Dewey Beach, Delaware.

Dewey Beach isn't exactly a big place. After all, it's only a few streets across, and a few blocks long just south of Rehoboth Beach. But in the summer, it feels as though the entire East Coast is crammed into it. The Atlantic Ocean's on one side, Rehoboth Bay's on the other, and in between are bars, restaurants, and rental houses with towels draped over the railings. You can walk from a packed beach to a crab shack to a full-blow cover band concert without crossing more than two streets. Dewey Beach is known for its nightlife, and The Starboard is the center of it all. So much so that it even has multiple sister restaurants, some within a block's distance, that offer different dining experiences. Live music spills from places like Bottle & Cork and from Rusty Rudder's bayside deck, where you can watch the sun sink into the water.

Selbyville

Scenic waterfront properties in Selbyville, Delaware.
Scenic waterfront properties in Selbyville, Delaware.

Right up against the Maryland state border, Selbyville has long been a town that straddles both Delaware's rural and coastal worlds. Its downtown still shows off bits of its 19th-century railroad past, but it's what's cooking that really gets attention. La Sierra, both a restaurant and Mexican grocery, is the kind of place people drive an hour for. Over on Main Street, On the Way Cafe dishes out massive breakfasts with zero pretense, and the Little Italy Food Truck pulls regulars from both sides of the state lines. Just outside the center of town, the Freeman Arts Pavilion packs its summer calendar with national acts. And if you need a quiet reset, there's the edge of the Great Cypress Swamp, Delaware's largest forest, so dense and flat it practically swallows sound.

Milford

Riverwalk in Milford, Delaware.
Riverwalk in Milford, Delaware.

Milford's heart beats along the Mispillion River, where old shipyards and art galleries now sit side by side. The town's walkable downtown, especially North Walnut Street, still leans into its past, with restored 19th-century facades and a riverside stretch that locals simply call The Riverwalk. The path winds past Goat Island Nature Area and toward the Vinyard Shipyard, a living tribute to the town's boatbuilding roots. The nearby Riverfront Theatre fills its small stage with big-hearted productions, and just outside of town, the DuPont Nature Center draws birders and naturalists from across the coast.

Fenwick Island

Crowds enjoying the surf fishing beach at Fenwick Island, Delaware.
Crowds enjoying the surf fishing beach at Fenwick Island, Delaware. Image credit Khairil Azhar Junos via Shutterstock

Fenwick Island may share a border with Ocean City, Maryland, but its pace is several gears lower. This small Delaware town, set snugly between the Atlantic and Little Assawoman Bay, keeps things local and unfussy. Fenwick Island State Park claims a long stretch of beach right at the edge of town, with space to swim, fish, or just let the breeze undo whatever stress you brought with you. A short walk inland, the historic Fenwick Island Lighthouse, which was built in 1859, still marks the coast. While much of Fenwick Island is serene and peaceful, you can get louder at Viking Golf and Thunder Lagoon, where go-karts, mini golf, and waterslides come together on one lot.

Delaware isn't a state with over-the-top attractions or touristy gimmicks. But it does have a collection of beautiful towns that blend nature, history, and a great food scene together in an unpretentious way. Some are busy party towns like Dewey Beach, others are sleepy getaways such as Milford and Middletown. None of them compete with one another as they all offer something for a different kind of person. But each is honest, grounded in that specific Delaware vibe, and ready for you to visit.

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