1. Wilmington
Although Wilmington is the largest city in Delaware with some of the less attractive urban related issues, this city is still a lovely place to retire. Cost of living expenses are higher, but the housing costs are more affordable, and there are many great healthcare facilities albeit a bit higher priced than the national average.
Wilmington has lots of historic charm with architecture on the many older estates showing their French influence.
There are a lot of things to see and do here from cultural events such as the city’s opera house, museums and upscale dining venues. There are many interesting locales to visit like the stunning riverwalk, a local zoo and to many beautiful, shaded parks and other nature areas.
Highlights
- Located on the gorgeous Delaware River with quaint riverwalk and water activity opportunities
- Near to several terrific retirement communities
- Affordable housing
- Close to topnotch medical care
- Brandywine Zoo, Delaware Children’s Museum
- Music at its best at the Grand Opera House
- Hagley Museum and Library
- Historic history with French-inspired old-world charm – Nemours Estate
- Visit the prestigious Delaware Arts Museum with its Copeland Sculpture Garden
- See the Old Swedes Church for nostalgia and proof of the city’s wide attractive power
- Tour historic Winterthur Estate with lovely gardens – once home of Henry Francis du Pont
2. Rehoboth
Situated along the shores of the Northeastern beaches of the majestic Atlantic Ocean, Rehoboth offers retirees an affordable beach town lifestyle that has lots to see and do year-round for its independent residents.
This city boasts a family-oriented, mile-long boardwalk that is packed full of fun and healthy pursuits along with the sort of classy cultural draws that generally appeal to the aging senior population here which is sizable for the town’s size.
While housing is a bit expensive, there are nearby retirement communities that offer much at an affordable cost. Health-oriented retirees can participate in yoga on the beach, walk the many nearby nature trails that meander through many of this beach area’s prime eco-systems with its robust wildlife. Birdwatching is a popular hobby here.
Grab a bowl of steamy-hot New England clam chowder during the Seafood Festival held downtown annually. Watch the lively parade and browse the uniquely charming stores taking advantage of the zero sales tax.
Treat your grand-kids to fun activities and grab a taste of other culinary favorites here from around the globe. Top it off with a signature drink from the friendly pubs, and then relax on the beach while listening to live music.
Highlights
- Friday night musical concerts at Rehoboth Beach Bandstand in Summer
- Funland – an iconic amusement park
- Gordon’s Pond Trail and Cape Henlopen State Park
- Rehoboth Walking Food Tours
- Delaware Seashore State Park – camping, hiking, horseback riding
- Hop the Jolly Trolly to nearby beach attractions with narrated tours
- Fisherman’s Wharf Dolphin Watching Cruises
3. Dover
Delaware’s capital city of Dover is the second largest city in the state but is the largest overall employer that is home to the Dover Air Base and the informative Air Mobility Command Museum.
Learn all about Dover’s rich agricultural background by visiting the Delaware Agricultural Museum and Village with its historic buildings that open a window into this old-fashioned way of life.
Many retirees retire here for the city’s impressive selection of cultural arts including dance, theater, art, diverse musical history and fine dining establishments.
Feel the energy of NASCARs presence at the local Dover Motor Speedway, try the great golfing greens and enjoy easy access to the gorgeous Delaware River and nearby beaches.
Unlike Holly Hills in the Colorado state, Dover experiences typical urban crime rates in some neighborhoods, but the city’s pluses include reasonable cost-of-living expenses and affordable senior communities nearby.
Highlights
- John Dickinson Plantation
- Gambling at Dover Downs Casino
- Biggs Museum of American Art
- Firefly Music Festival
- Fresh local produce and Amish market at Spence’s Bazaar
- Fordham Brewing Company
- Swartz Center for the Arts and Children’s Theatre
- Dover Green Historical District
4. New Castle
Retirees wanting a smaller city lifestyle with lots of fun things to see and do every day will find New Castle an idyllic retirement community. This city offers a larger retirement population with affordable housing and access to nearby retirement communities and proximity to great healthcare facility options.
In addition, the easy commutes to nearby bigger city attractions make this town enticing.
New Castle has a lot of old-fashioned historic charm for its smaller size. and there are lots of nearby Delaware beaches and water adventures to enjoy along the stunning and scenic Delaware River where this city is situated.
Highlights
- Amstel House
- Hagley Museum and Library in nearby Wilmington
- New Castle Court House Museum
- Access to terrific beaches and Delaware River
- George Read II House
- Mid Atlantic Grand Prix
5. Milford
Milford is known for its outstanding art community and its scenic central location in Delaware. Residents have access to the beautiful Delaware Bay beaches with all their lovely views, water activities and unique wildlife.
There are several nature centers here, and locals can walk this town by foot or take advantage of low-cost bike rentals to ride or walk the well-kept paved trails.
Sample the delectable food choices from local only dining venues and browse the exquisite art galleries and small shops along the quaint Riverwalk.
Find gorgeous, one-of-a-kind artwork including jewelry, paintings, clothing and more handcrafted by this area’s talented artisans. Female artists are proudly showcased during the town’s annual Ladybird Music Festival and block party available to all in September.
Highlights
- Mispillion Art League offers art classes for adults and kids
- Access to Bayside beaches and nature centers
- Rent a kayak for river adventures
- Stay at The Towers a Victorian-era bed-and-breakfast
- Causey Mansion with stunning gardens 1690 circs land
- Milford Museum
- Seaford Walking Tours – sample local craft beers and local cuisine
6. Middletown
Bordered by the Delaware River and Maryland border, Middleton offers senior residents a comfortable, smaller city lifestyle featuring a sizable retiree population and a number of 55-plus communities.
Middletown is ideal for healthy seniors that prefer a mix of historic charm and small-town recreational pursuits outdoors like birdwatching, exploring nature parks and enjoying water adventures in warm weather months.
Middletown got its name from its original place along a historic trade route being about midway. While costs-of-living are a bit higher than national averages, the lower crime rate, tax-breaks for seniors, less expensive healthcare access and no state retail tax make this town a viable retirement selection.
Highlights
- Middletown Historical Museum
- Gabby Center for the Arts
- Durch Country Farmer’s Market
- Visit Middletown Village and Silver Lake Park
- Creation Station – make your own art
- See live performances at historic Everett Theatre
- Head to nearby Odessa to tour Corbit-Sharpe House – a historic mansion in the Philadelphian-Georgian architectural style
7. Seaford
Located in the gorgeous southern region of Delaware, Seaford is often listed as one of the best small towns to live. The beautiful Nanticoke River provides many water adventures like swimming, kayaking, boating, cannoning and fishing. Swimming is also popular here in summer months.
There are lots of nature parks and scenic trails and other available outdoor recreational pursuits to enjoy, and the town also boasts a fair number of arts and other cultural attractions too making it a dream retirement locale for many.
This city also has a storied history with a surprising number of restored architectural structures from colonial times.
Highlights
- The Seaford Museum
- Governor Ross Mansion – a historic plantation house
- Catch the Woodland Ferry to cross the Nanticoke River to Woodside
- Experience Delaware nature at Nutter, Kiwanis or Gateway Parks
8. Milton
At the head of Broadkill River in Sussex County lies the small, older town of Milton has a long political history here. This location, with Delaware Bay just south, prompted the town’s lumbermill, shipbuilding and shipping industries.
Today, the local economy is driven by recreational boating, fishing and other largely tourist industries, granaries, construction and sign manufacturing along with agriculture.
The sizeable retiree population, affordable homes, low crime and stunning nature scenes draw many seniors looking for a small town with some noteworthy cultural draws.
Close access, to beaches in Lewes and to Redden State Forest, provides many trails for hiking along with and other outdoor pursuits.
Highlights
- Dawn/s Country Market
- Dogfish Head Craft Brewery
- Prime Hook National Wildlife Refuge
- Milton Memorial Park
- Milton Theatre
- Lavender Fields Farm
9. Newark
Newark is a picturesque small city that boasts lots of green parks and outdoor activities. Located in the northwest corner near the Maryland border, this college-town is home to the University of Delaware and has an upbeat and eclectic vibe that keeps retirees feeling young and spry.
The city offers many cultural events and attractions including theater, museums and several historic landmarks.
Visit Christiana Mall, catch a game at the Bob Carpenter Center, view Revolutionary War era military equipment at The Pencader Heritage Museum or dine out at many fabulous area restaurants. The city boasts low crime and lower housing costs.
Highlights
- Hill Billy Hills Alpaca Farm
- White Clay Creek State Park
- Iron Hill Park and Glasgow Park
- Hale-Byrnes House historical landmark
- Midnight Oil Brewing Company
- REP Theatre – University of Delaware
- Fred Rust Ice Arena
- Iron Hill Science Center
10. Georgetown
Some call Georgetown “The Historic Jewel of Sussex County,” and with the city’s old-fashioned charm and historical treasures, it is easy to see why so many retirees settle down here.
There are interesting museums to explore, good food, fun community events and cultural venues galore.
Although the crime rate is higher than average, the topnotch healthcare and housing in this region is reasonable.
Horse drawn carriages, scenic wonders to explore, outdoor recreation options, local wildlife educational centers and more await in this gem of a city that should be considered for your future retirement paradise.
Highlights
- Historic Georgetown Train Station
- Marvel Carriage Museum
- Red Barn Country Store
- Redden State Forest
- See old military planes at Delaware Aviation Museum
- Sports at the Beach
- Mulligan’s Pointe Golf Course
FAQs about retiring in Delaware
1. Why should seniors consider retiring in Delaware?
A: Delaware has no retail tax, offers tax incentives for seniors and its property taxes are among the lowest in the nation ranked 6th with additional tax credit for school property taxes. This ideal state for retirees has gorgeous scenery and plenty of regional attractions.
2. What are a few unique characteristics of Delaware that would interest retirees?
A: Not far to beaches, city cultural venues and pristine northeastern nature environments wherever you live in the state. Delaware is also tax friendly, diverse and offers a rich history as the nation’s first state.