8 Charming Delaware Communities To Retire Around Wilmington
Wilmington is the largest and most populous city in Delaware, the second smallest state in the US. Delaware comprises many rivers, lakes, and mountains, making it an ideal state for retirees, especially in the small communities around Wilmington. Retirees can look forward to a safe, wonderful life with like-minded people and plenty to do and see, whether it is a seaside town or inland in beautiful Delaware. From New Castle to Hockessin, these charming small towns have well-maintained hospitals and amenities, as well as affordable housing.
New Castle
New Castle, a riverfront community and a National Landmark Historic Area, is mainly a residential town with most structures renovated and restored to their colonial elegance. Maintaining its proud history, Newcastle has several museums: The Dutch House, one of the oldest houses, The Amstel House, Governor N. Van Dyke’s home, The Old Library, housing exhibits of Fort Casimir, and the 1732 Court House Museum. It is a lively town with many events, like a treasure hunt in the farmers' market and the Annual A Day in Old New Castle, with pirates, historical reenactments, and music. A sight that cannot be missed is the Delaware Memorial Bridge between New Castle and Pennsville, New Jersey. The bridge was built in memory of those fallen in WWII, the Korean Conflict, Vietnam, and Desert Storm.
Although only 15 minutes from Wilmington, New Castle has excellent health care at ChristianaCare and an affordable housing market with a median sale price of about $330,000 (in January 2025).
Claymont
Near the Naaman’s Creek mouth on the Delaware River is Claymont, a quintessential town for retirees. For those who love exploring a town's history, Claymont has many historic places, such as Archmere Academy, Darley House, and the Claymont Stone School, founded in 1805. Outdoor enthusiasts will enjoy Lesher Memorial Park, Radnor Green Park, Woods Haven Kruse Park, and Perkins Run Park, which have play areas for kids, picnic areas, and trails for strolls or more challenging hikes through the splendid natural environment.
The median home sales price in Claymont is in the $333,000 range. Healthcare concerns are never an issue at Claymont Walk-In Care or Henrietta Johnson Medical Center (in Wilmington). Claymont is only a 14-minute drive from Wilmington, so it is never far from the city's hustle and bustle when needed.
Middletown
Only 35 minutes from Wilmington, Middletown has something of interest for every retiree. Originally a tavern stop, Middletown offers everything a big city offers but with a cozy small-town ambiance. The median home sales price is around $437,000. ChristianaCare’s Middletown Free-Standing Emergency Department or CareCenter are the go-tos for medical emergency concerns with modern full-service facilities.
Furry retirees will especially love living in Middletown and mingling with friends at the Levels Road Dog Park in the Charles Price Memorial Park. Surrounded by farmlands, the 100-acre park includes walking trails, fishing, playgrounds, and pavilions with grills. It is a popular spot for ducks, Canadian geese, and snow geese. There is also the Middletown Main Street Pocket Park. It is in the center of the town's busyness, with a designated green space of splendid landscaping for a casual stroll and benches to sit and watch the world go by.
The Everett Theater showcases performances, events, and movies and hosts various art and filmmaking classes. This little town offers a variety of shops and restaurants, but breweries, like First State Brewing Company and Jakl Beer Works, are a hot favorite.
Rehoboth Beach
Rehoboth Beach is ideal for those wanting to retire under warm sunshine and pristine oceans. Although a significant attraction for tourists, the tranquil lifestyle along the mile-long beach, only an hour and a half from Wilmington, makes it a suitable option. However, it is hardly a dull town. The Summer Concert Series hosts many artists in the town for live entertainment. From May to October, the farmers market is open every Tuesday with local vendors offering fresh and hand-crafted products like pottery, candles, aromatherapy, and raw and baked food products. Rehoboth's Boardwalk comprises shops for every occasion, from art to antiques, bookstores, grocery, pet, and surfing stores.
Most retirees' biggest concerns are healthcare and housing markets. Beebe Primary Care in Lewes has everyone covered for annual physicals, routine screenings, minor injuries, and chronic disease management. The housing market is perhaps pricier than other small towns, with a median sale price of about $995,000, but the quality of life in Rehoboth Beach makes up for it.
Lewes
Where the Delaware Bay and the Atlantic Ocean meet at Cape Henlopen, an hour and a half from Wilmington, is stunning Lewes, a retiree dream. Due to its superb location, it is expected to be a high-cost living. However, the housing market has decreased slightly at a median sale price of about $700,000.
The historic district and an eclectic range of restaurants, like coffee shops, steak houses, seafood, and fine dining, as well as shops, like antiques, interior design, art, sports, and clothing, are all within walking distance around town. The Zwaanendaal Museum offers a peek into Lewes' maritime, military, and social history.
Hiking and bike trails are popular, like the Junction and Breakwater Trail, Gordon's Pond Trail, and the Beach Hiking trails. Cape Henlopen State Park, with 5,000 acres, is full of stupendous nature and abundant wildlife. The park also includes the Seaside Nature Center, the Fort Miles Historical Area, and bike paths on the ocean and bay beaches.
Making retirement complete in Lewes is the excellent healthcare at Beebe Healthcare facilities, where all health concerns are cared for.
Milford
Those who enjoy art, culture, and history would enjoy retiring in Milford, almost 70 miles from Wilmington. The Milford Museum will enthrall history enthusiasts with artifacts from shipbuilding to wooden spoons and its many events, like The Secret Rosies of WWII and Lincoln’s Final Hours. The Second Street Players at the Riverfront Theater is a year-round community theater that produces quality musical, drama, and comedy productions.
Milford has no shortage of shops and shopping malls, like the Milford Village, with over 100 shops, including boutiques, retailers, and restaurants. It also hosts events, craft fairs, and live music. The Big Oyster Brewery offers evening entertainment of music, laughter, and good food.
Like most smaller towns in Delaware, Milford is surrounded by natural beauty as the Mispillion River intertwines through Milford's downtown. The Mispillion Riverwalk provides plenty of fresh, healthy air, stunning scenery, wildlife, and the best views of Milford. At the end of the Riverwalk, it connects with the Goat Island Nature Trail, which is equally inspiring.
With so much to offer Milford, even the housing market is affordable, with a median sale price of about $320,000. Bayhealth Hospital, Sussex Campus, will care for health concerns, making retiring in Milford a fabulous choice.
Bethany Beach
Retiring, for some, means slow walks on the beach, watching the sunset, browsing shops on the boardwalk, and easy hiking trails in nature parks. Almost two hours from Wilmington, Bethany Beach has all this and more, particularly highly-coveted housing at a median sale price of about $3M and outstanding health care at Beebe Healthcare in Lewes.
The Bandstand is a must for music lovers. Shows include rock, pop, country, and jazz, usually starting at 7:30 pm in summer and 6:30 pm in the fall. Bethany Beach might be a casual, laid-back town, but it has exciting and fun events for all ages year-round, like the Poseidon Festival, the Songwriter Showcase, and the Independence Day Celebration.
Being one with nature is part of living in Bethany Beach. Take a stroll through the Baldwin Nature Trail through a wetland and a maritime forest and discover over 100 wild bird species, minnows, reptiles, and amphibians. The Addy Cottage, built in 1903, houses the Bethany Beach Nature Center. Step inside to learn about Bethany Beach's natural world.
The Boardwalk in Bethany Beach is ½ mile long and has restaurants and shops for every taste. While walking along the Boardwalk, breathe in the salty air, let the sea air frizz your hair, and enjoy the spectacular views of the ocean.
Hockessin
Only 20 minutes from Wilmington, Hockessin is highly suitable for nature-lover retirees. The Mt. Cuba Center, once farmland, is a splendid botanic garden home to many native plants. The center hosts ongoing classes and events to educate and inspire enthusiasts. A must-visit is the Ashland Nature Center, which includes trails and a hawk watch, and in summer, the Butterfly House is a sight to behold; species include the Monarch, the blue spotted, and Delaware’s official butterfly, the Tiger Swallowtail.
Auburn Valley State Park makes it easy to stay healthy and active. It includes several hiking and biking trails. An interesting feature is a collection of operational steam cars and a miniature coal-powered train that runs on tracks around the estate. After hiking or biking and viewing the cars, visit the Auburn Heights Mansion and flashback to the Victorian era for a while.
Historical landmarks are plentiful in a town as extraordinary as Hockessin. Significant historic structures are The Ashland Covered Bridge and the 1738 Hockessin Friends Meeting House.
Hockessin might sound too good to be true, especially with its exceptional health care at ChristianaCare and competitive housing, with a median sale price of about $680,000.
Delaware is an ideal state for seniors to retire in. Around one of its central towns, Wilmington, are smaller towns suitable for a tranquil lifestyle where life is easy-going, casual, and as social as desired. These towns are historically proud and surrounded by natural wonders. Conservation and preservation are essential to the communities where newcomers are encouraged to become involved. Housing and healthcare are primary concerns for retirees. Fortunately, these are covered adequately, so choose a town near Wilmington and enjoy a retired life.
