Like living in a fairy tale, Arden is known for its unique origin story. It was founded in 1900 by sculptor Frank Stephens and architect Will Price as a utopian retreat. It includes the Arden Gild Hall, where you can enjoy community dinners and concerts by big names. There is also an outdoor theater. The entire community is on the National Register of Historic Places.
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Parks, walking trails, neighborhood parties and, of course, the Bear Drive-In. Downtown also features a seasonal farmers market. Bear has its history in agriculture but is now more reminiscent of a suburb with spacious lots and a variety of single-family and townhouse properties. Local offerings include a Boys and Girls Club, a Wilmington University location, a library and an art gallery.
Bellefonte can be considered Wilmington’s quirky little sister. The town was incorporated in 1915 and connected via trolley line to Wilmington. Today, the connecting line, Brandywine Boulevard, highlights the area’s artists and crafters. Bellefonte Arts, founded by Valeria White, sells wares created by more than 40 artists and artisans and offers classes. Bellefonte Café serves up local brews and eats, plus open mic nights and live music ranging from bluegrass jams to swing. Each year, crowds flock into town for the Bellefonte Arts Festival, a celebration of the visual, performing and culinary arts.
Nestled in Wilmington between Brandywine Park and Route 202, the Triangle blossoms with urban gardens and communal energy. Residents can also join the neighborhood association, which for a small fee offers a community newsletter and events, as well as volunteer surveillance, so neighbors can feel safe knowing everyone is looking out for one another. Most homes were built in the 1920s, a pleasant mix of tidy semidetached homes in red brick or stone, with a few single-family residences built in Craftsman style, with angular, columned porches.
The Highlands is an upscale community in the city of Wilmington, home to such landmarks as the Delaware Art Museum, Rockford Park and Ciro Forty Acres, where on weekend mornings neighbors often spill out onto the bistro tables to share breakfast hash and conversation. Enjoy weekly summer concerts in Rockford Park. In May, head to the Wilmington Flower Market, a three-day annual event with amusements, crafts, foods and an array of plants.
With fewer than 1,000 year-round residents, South Bethany lives up to its reputation as a quiet resort. Life revolves around the water, with a beach ranked one of the cleanest in the nation and a 5-mile network of canals conducive to boating, crabbing and fishing. Construction is ongoing in South Bethany, as it continues to be a prime relocation and retirement spot.
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The Centreville landscape is dotted with du Pont mansions and other estates dating back to 1711, when Friends Centre Meeting House was built from logs. Today, Kennett Pike, the main thoroughfare, is lined with historic buildings that house businesses. In town, there are art galleries and antiques shops. You can buy flowers at Wild Thyme and indulge in gourmet goodies, to dine in or take out, at Centreville Café and Montrachet Fine Foods. Check out Buckley’s Tavern, built in 1871, which was remodeled just a few years ago.
A bustling downtown and community events are big draws to Middletown. Reflecting the trend toward pedestrian-friendly locales, Middletown is on the comeback trail. A long-vacant bank is now La Banca, an Italian restaurant. There are gift shops, a tailor, a karate school and a spa. Thespians tread the boards at the Everett Theatre, featured in the film Dead Poets Society. In mid-August, the town hosts its Annual Middletown Old-Tyme Peach Festival. Throughout the year, shops and dining spots promote events like Yappy Hours, where patrons are invited to bring their dogs for a mingle downtown.
From a historic perspective, Claymont is a tale of two cities. Robinson House, built in 1723, was the home of Col. Thomas Robinson, who hosted George Washington. John Jakob Raskob, a DuPont executive and builder of the Empire State Building, lived in the mansion that is now Archmere Academy, a celebrated Catholic prep school. The other half of this community on Philadelphia Pike was centered on the steel mill. Modest housing was constructed for workers, with grander homes for managers. President Joe Biden dreamed of attending Archmere from his boyhood home, an apartment building across the pike. (He made it.) Today, Claymont is evolving with employees heading to the train station instead of to the mill.
Wyoming, population 1,313, calls itself “the best little town in Delaware.” Most homes in the central district are on the National Register of Historic Places, built soon after 1856, when the community was established as a stop on the Delaware Railroad. The town merged with Camden in 1975. The combined town blends both new and old with agriculture mixed with history and newer homes. Wyoming celebrates its own Peach Festival each August, and nearby Fifer Orchards, a fourth-generation farm, hosts multiple events, a CSA and u-pick experiences.
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The First Town in the First State, downtown Lewes appeals to people with an appetite for history and food, from maritime art at the Mercantile Antique Gallery to a scoop of butter brickle at King’s Homemade Ice Cream. Shipcarpenter Square is a community of centuries-old homes transported from Virginia and Maryland, including a repurposed lifeguard station. A hub for foodies, Lewes has the original Agave, Heirloom and Raas for your Indian cravings. Coming soon is a new oyster house, which will join other local favorites Striper Bites, Kindle and Harvest Tide out toward the beach.
Remote and beautiful, Yorklyn’s fortunes waxed and waned with those of industry, from snuff mills in the 1800s through the National Vulcanized Fibre Corporation (NVF) plant, which closed in 2008. Yorklyn Village is a work in progress that includes retail, restaurants and housing on the NVF site. A trail system connects the village with the nearby Marshall Steam Museum and the Delaware Nature Society. Yorklyn has become a cultural destination with the Center for the Creative Arts, which supports visual and performing arts and hosts a summer camp for kids. The center is the site of the annual Yorklyn Storytelling Festival.
More than a mile from the Atlantic, Ocean View was so-named because residents in the late 19th century could see the sea from their second-story windows. In 1923, Delaware’s fledgling poultry industry was hatched there. Today, the community includes Bear Trap Dunes, which features an extensive pro shop, a swanky New Year’s Eve party, and food and drink specials for sports-watching enthusiasts in The Den.
Settled in 1675 on the Broadkill River, Milton is considered the next frontier for beach living. Once a center for shipbuilding, button-making and holly, the town has 198 buildings in its federally designated historic district. On Union Street, stop in for a slice or a whole pie at The Dough Bar. Get your antiquing on at The Mercantile. Or stop in for a show across the street Milton Theatre, built in 1910, which hosts films, theatrical productions, comedy and children’s performances.
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Known as America’s Summer White House, Rehoboth Beach has evolved to a year-round destination, an energetic blend of homes, galleries, shops, bars and restaurants. The closer properties are to the beach, the higher the price tag, but the better the views. Although in this sweet city, there may not be a bad view. Known internationally as a gay-friendly community, the town is the home of CAMP Rehoboth, a nonprofit dedicated to creating a positive environment inclusive of all sexual orientations and gender identities.
Long and narrow, Dewey Beach has the distinction of offering both ocean and bay views, sometimes from the same location. With a reputation as a party town for college kids, Dewey boasts large, loud venues, including concert hot spot the Bottle and Cork and the Rusty Rudder, with a bayside deck for al fresco imbibing. Check out The Starboard for its signature Bloody Mary smorgasbord. The north end of town is more family-oriented, with new construction of 5,000-square-foot-plus homes. With fewer than 400 year-round residents, most of the housing is vacation homes, rentals and combinations thereof. Residential inventory increased significantly when three hotels were converted to condominiums.
Home to the University of Delaware, downtown Newark is an exuberant blend of academia and culture. The tradeoff is a paucity of parking and chronic construction. Southwest of campus, just beyond student housing, lies Old Newark, a tranquil pocket of homes that is walkable to downtown. Enjoy theater, music, art, nature, athletics, festivals and socializing in a compact town that merges university and community cultures.
Captain John Smith sited Seaford in 1608, when he sailed the Nanticoke River as part of his mission to explore the Chesapeake Bay. In 1939, the DuPont Company built its first nylon plant there, making Seaford the Nylon Capital of the World.
From Dover’s Historic Green to the Old Statehouse to the Johnson Victrola Museum, Dover is a mix of new and old. The downtown streets are pedestrian-friendly and were laid out in 1683 by William Penn.
Get a feel for art new and old at the Biggs Museum of American Art and belly up to the bar of history at the rebuilt Golden Fleece Tavern, where legislators voted to ratify the Constitution in 1787 and patrons can still hoist a mug of Fordham & Dominion beer.
Related: The Bear Drive-In Offers Nostalgic Film Screenings in Delaware