Downtown Lewes, Delaware from bridge with canal.

9 Best Small Towns to Retire in Delaware in 2024

Delaware is a small yet stunning US state located along the Atlantic Ocean. In terms of size, Delaware is only a little bigger than Rhode Island, the smallest state of the union. However, despite its size, Delaware houses many state and national parks, which are protected by the state and preserve the flora and fauna of the charming coastal state. Towns like Bethany Beach are ideal for anyone who enjoys boating and swimming in the Atlantic Ocean, while towns like Hockessin sit conveniently close to parks and nature sites like Ashland Nature Center and White Clay Creek State Park.

Delaware is also a community that celebrates together. Small towns often come together to host events almost every year, but 2024 is a particularly exciting time to be in the area. Lewes is hosting its annual Christmas parade, and Rehoboth will be hosting its "Santa Claus is Coming to Town." Summer is also a time of activity, with celebrations like Rehoboth Beach's Outdoor Fine Art and Fine Craft Show in August.

Those in retirement often seek out a place that is welcoming and peaceful and enables them to have an active lifestyle. That makes Delaware the perfect state to retire. The small towns make anyone feel right at home and like they are part of the community. Whether a retiree seeks a rural suburban community conveniently close to large cities like Wilmington or desires to set up shop along the shores of the Delaware River, there are plenty of options in Delaware for everyone.


Downtown Milton, Delaware.
Downtown Milton, Delaware. Image credit Khairil Azhar Junos via

Milton is an ideal spot to retire since it offers a charming small-town environment conveniently close to several key Delaware locations. Its relative proximity to Delaware Bay made it an important place during the early years of the state, and the community’s shipbuilding skills were rather famous. Milton is not as well known today for its shipbuilding industry, but it provides a wholesome location to settle down and has first-class care centers and health facilities. One of the most notable accommodations is the Luther Towers, run by the Luther Senior Services Incorporated.

The Luther Towers provide residents who are 62 or older with comfortable living and convenient care services. As a resident of this facility, individuals can access the DART bus, as well as enjoy on-site recreational and social activities. It’s a great option for those seeking a combination of senior care and an active lifestyle. Although, there are plenty of other housing options for those who are seeking an independent living space, including homes and apartments. Shipbuilders Village, a cozy little village in town, has some lovely condos that are fantastic for retirement.

The small community is conveniently located near a few nature sites, meaning it is perfect for anyone who enjoys going outside. Deep Branch Family Campground is an adorable place to spend a day or even a whole weekend immersed in nature. The campground is just a few minutes outside of town and has access to nearby beaches and hosts on-site events throughout the season. This year, locals and visitors alike can enjoy events like Walk into Wholeness and live music at the local chapel every Sunday.

Bethany Beach

Coastline at Bethany Beach, Delaware.
Coastline at Bethany Beach, Delaware.

Bethany Beach is just under an hour from Milton and sits right along the coast of the Atlantic Ocean. Its shores are known for being some of the cleanest and are popular spots for swimming, boating, and beachcombing. Bethany Beach Central Park is a lovely town park that is ideal for a picnic or leisurely stroll. For active seniors who like group activities, Cheer, a special place for seniors to mingle and engage in activities like yoga and music, operates just under 10 minutes from town.

Bethany Beach has plenty of spots to put down roots in town, including the Villas of Bethany West Condos. These homes are designed for folks of all ages and are conveniently located in town and include amenities like a swimming pool, basketball court, and other outdoor activities. They're also not far from the Bethany Beach Canal, a lovely place for a walk or to take photos, and residents do not have to travel far to get to Bethany Primary Care.


Redbud tree in full bloom at Mt. Cuba Center, Hockessin, Delaware
Redbud tree in full bloom at Mt. Cuba Center, Hockessin, Delaware.

Hockessin is nearly two hours north of Bethany Beach, just along the border of Pennsylvania to the north. It is best known for the old ruins of Garrett Snuff Mill, which also bears the name of George W Helme Company, situated just outside the town’s borders to the east of the neighboring Yorklyn Mills. The company was once a thriving manufacturer in the community until the site closed in 1954, only to be designated on the National Register of Historic Places in 1979.

The town is close-knit and safe, with just under 14,000 residents. The Brookdale assisted living center is a highly-rated care center in town for those seeking a quiet place. However, for those hoping to have a more independent place to live, there are plenty of homes and fine apartments available, both furnished and unfurnished.

It is the ideal destination for nature lovers who enjoy a calming stroll in the woods or a more intense hike through the surrounding areas. The Mason-Dixon Trail is a popular hiking spot along the Hockessin-Yorklyn border, and is a fairly easy trail to hike and usually only takes around 20 minutes to complete. Another exciting outdoor location is the Ashland Nature Center. It is popular for people of all ages, with a butterfly house, hawk watch, lots of different types of plants and flowers, and it only costs $5.00 to visit.


Canalfront Park in Lewes, Delaware.
Canalfront Park in Lewes, Delaware.

Traveling about an hour and a half south of Hockessin along the banks of the Delaware Bay is the town to Lewes. It is a beautiful coastal town with a small population of approximately 3,500. It is also a great place for seniors who hope to stay active and involved in a thriving community of energetic individuals, no matter their age. It is also a city filled with historic and natural sites like Fort Miles, a couple of minutes outside the community’s main borders, situated near Cape Henlopen State Park.

For those who enjoy an independent life, there are plenty of homes and apartments in town. However, for those who hope to have a more luxurious retirement, there are places like the Lodge at Historic Lewes. The family-run community offers a unique retirement experience that includes services like housekeeping, linen washing services, dining, and other amenities you usually only find at a hotel. Not far away is the Lewes Senior Activity Center, which keeps people engaged, happy, and active for just $35.00 per year.

Retirees seeking an exciting day out on the town won’t be disappointed either. Lewes has excellent waterfront dining spots like the Irish Eyes Restaurant and Pub or the nearby Harvest Tide Steakhouse. Finally, locals can look forward to getting outside and exploring the many parks and trails, including the Junction and Breakwater Trail, a 5.8-mile trail in the woods that’s fairly easy and ideal for those who enjoy a bike ride.

Rehoboth Beach

People at Rehoboth Beach, Delaware.
People at Rehoboth Beach, Delaware.

Rehoboth Beach is an adorable small town not far from Lewes. Its history dates back to 1891, when the Delaware General Assembly changed the area’s name from Henlopen to its current name. Back then, the community started to see the creation of the now famous mile-long boardwalk, which runs along the shoreline and serves as one of the town’s most iconic tourist locations. While this coastal community is best known as a popular tourist stop with lots of spots to eat and play games, it is also a convenient and welcoming place to live and enjoy retirement.

One of the best retirement communities is the Lodge at Truitt Homestead, where wholesome cooked meals are provided and an atmosphere of wellness is created. Seaglass at Rehoboth Beach also provides residents with an opportunity to live a luxurious life on the shores of the Atlantic Ocean. The site has a couple of floor plans to choose from, including a single-bedroom up to a three-bedroom floor plan with a porch or balcony. The homes also have access to the pool, fitness center, and other amenities while living at Seaglass.

The seashore town is active, meaning it is a great option for retirees who want to live an engaged lifestyle, walking the boardwalk, playing games on the beach, and enjoying local cuisine. Funland is an exciting outdoor park with rides, games, and great food. Residents can enjoy a fresh cup of coffee at the Rise Up Coffee Roasters and consume a delicious meal at Dogfish Head Brewing and Eats. Or, visit Henlopen City Oyster House and grab fresh, delicious oysters prepared, cooked, or raw.


View at the beginning of the walk on the Milford, Delaware River Park walkway.
Milford, Delaware River Park walkway.Image credit Don Garrard via

Milford is a central Delaware community located approximately 30 minutes northwest of Lewes. Milford is the ideal place for artful living since the community has stunning natural landscapes blended with the artistic touch and charm of its history and residents. Haven Lake and Silver Lake are the town’s lovely waterways located near the town’s western point and are largely to credit for the community’s natural beauty.

The city celebrates its heritage at the local museum, where guests can view artifacts and learn about Milford’s past. Residents and visitors alike can partake in the amazing festivals, which include the Bug and Bud Festival, Holiday Stroll, Memorial Day Flags for Heroes, Community Parade, and the Ladybug Music Festival. Each event draws the town’s residents closer together and allows tourists to learn about and celebrate the charming little city. Those who enjoy nature may also appreciate the Mispillion Riverwalk and other community-directed nature strolls.

Milford has its very own senior center, called the Milford Senior Center. This site allows retired residents to participate in fun fundraisers like the Utility Tote Raffle and the Sub Sale Fundraiser. They also offer a community room, which people can rent for their own celebrations, and an activity center designed to keep folks active and healthy. Retirees can enjoy high-quality living at Milford Place, where residents experience care and various living options designed to meet different budgets. Lastly, residents have access to the Bayhealth Hospital (Sussex Campus) for all their needs and emergency treatments in nearby Dover.


Blue pick-up truck on the street in front of the Everett Theatre in Middletown, Delaware.
Blue pick-up truck on the street in front of the Everett Theatre in Middletown, Delaware. Image credit Alexanderphoto7 via

Middletown is a north-centrally located community near the Delaware-Maryland border. It’s a slightly larger town with around 24,000 residents, but still deeply connected. Meadowcrest at Middletown is a wonderful home for seniors located between the borders of Middletown and its neighbor, Odessa. It is a welcoming home that offers residents assisted living in a peaceful location designed to maximize health and well-being at all stages of life.

The Middletown Odessa Townsend Senior Center creates a community where senior retirees can meet new people and engage in activities like arts, crafts, bingo, bowling, and more. Golf enthusiasts will love Middletown because the town has not just one but two beautiful golf courses: St. Anne’s Golf Links and Frog Hollow Golf Club. Both boast a blend of high-standard courses and delicious foods to enjoy at the club restaurants after a day on the green. They also have fantastic places to sit and nurse a drink, with St. Anne’s Golf Links having its own beer garden and Frog Hollow Golf Club hosting a wonderful pub.

The Dutch Country Farmers Market is a convenient and charming destination where residents can purchase groceries and basic necessities. Charles E. Price Memorial Park in the southwestern parts of the community is a lovely spot to take a stroll, walk a dog, and gather with friends to enjoy the town’s weather and natural landscapes. Crooked Hammock Brewery is a popular gathering place in town, where they serve delicious types of tap beer. Metro Diner is a good restaurant to take family to get a well-made meal in a warm and welcoming environment.


Aerial view of waterfront homes with a private dock near Millsboro, Delaware, USA.
Overlooking waterfront homes with a private dock near Millsboro, Delaware.

Just under 40 minutes west of Rehoboth Beach is the beautiful town of Millsboro. Millsboro’s official history began in 1893 when it was created as “The Commissioners of the Town of Millsboro,” which primarily served to survey the area. Today, Millsboro is known as a quiet community that is family and retiree-friendly. Retirees will be happy to know that Millsboro has all the essentials right at their fingertips, including nearby assisted living options, supermarkets, and healthcare centers, as well as fun places to explore and enjoy.

The Indian River Senior Center offers many opportunities to connect with the town’s people and enjoy group activities. This place of gathering opens its doors several times per month to members, offering weekly lunches, bingo, and the occasional bus trip. The best part is that membership only costs $40.00 per year. Millsboro sits along the banks of Millsboro Pond, which has a boat launch for those who like a peaceful meander down the waterway or a day of fishing.

Cupola Park is near Millsboro Pond and is a popular destination for a day outdoors. The pavilion has a barbecue area and picnic area, meaning it is a convenient spot to have a gathering with friends and family. The Nanticoke Indian Tribe Center is on John J. Williams Highway and is an important location in town. This site preserves the cultural and historical heritage of the Nanticoke Tribe who live in the region and have lived there long before the arrival of Europeans.


The historic Odessa Bank on Main Street, Odessa, Delaware.
The historic Odessa Bank on Main Street, Odessa, Delaware. Image credit Khairil Azhar Junos via

Odessa is a neighboring town of Middletown, situated just east of this larger community. Even though Middletown is significantly larger, Odessa is a uniquely historical town, with the community’s historical center being one of its main attractions. Odessa is home to two National Parks Service Network to Freedom sites and a National Historic Landmark. The National Historic Landmark is the Corbit-Sharp House, built in 1774, and is worth visiting.

This location is just one of many examples of the historic significance of this community. New residents are sure to love the historical society of Odessa, known as the Historic Odessa Foundation. Not only can visitors learn about the history of their new home, but they will also have access to several beautiful gardens and the historic homes lining the 18th—and 19th-century roadways. The site hosts several events every year, with 2024 seeing such notable events as the celebration of Juneteenth, and basket weaving classes, among other immersive activities.

This close-knit town is more than just a historically fascinating location; it’s also the ideal place to make a home. For retirees, there are many conveniences to living in Odessa, including the Giant Food supermarket located under 10 minutes from Odessa in neighboring Middletown. There is also the holistic healing center Creative Medical Consulting, which offers whole-body and mind care to its patients. Residents can also enjoy things like Corner Grounds Cafe and Corbit-Calloway Public Library, meaning they will always have plenty to explore in town.

Retirement is an important part of life, but many people mistakenly think it means it is time to stop enjoying life. That is not the case at all, and much of a person’s enjoyment of retirement relies on finding the idyllic place to put down roots and call your new home. Fortunately, Delaware maintains safe neighborhoods that prioritize health, well-being, and the preservation of nature. The Delaware Parks Department maintains 17 State Parks, meaning residents almost always have easy access to beautifully preserved parks that showcase the state's landscapes and house wildlife.

Active retirees will have lots to enjoy outdoors in 2024 in Delaware. The Delaware State Parks Department has its Play Outside App, which updates locals and visitors alike with trail conditions and other important information to help them plan their outdoor activities this year.

After retirement, it is important to stay active and engaged in a welcoming community. Delaware’s many senior centers, golf courses, exercise facilities, activity centers, and other free or affordable resources make for the perfect places to experience just such a retirement. People can stay healthy, engaged, and sharp by making their homes in this small but welcoming state on the East Coast.

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