
Delaware is a hidden gem on the eastern coast. There are many appealing places to retire in Delaware, even though the state is often overshadowed by its larger and more popular neighbors Pennsylvania and Maryland.
Though it is a smaller state, only spanning 96 miles long and 35 miles across, it is big on history and culture. Nicknamed the “First State,” Delaware was the first of the original thirteen states to formalize the U.S. Constitution.
Delaware is not just the ideal state for history buffs, but also for those who love the arts and outdoors. Delaware is a perfect place for retirement for those looking for a quiet place to settle down. But retirees never have to worry about getting bored in Delaware.
Not only is there an abundance of outdoor activities, theaters, and galleries, in Delaware, but for the times you need to get away, it is conveniently located near enough to New York, Baltimore, and Washington, DC. Most residents can easily make a day trip to the larger metropolitan areas.
Filled with seaside towns, Delaware is a great state for those looking to retire near the ocean but without the high cost of living and the overwhelming number of people found in other oceanside states like Florida, California, or even the Carolinas.
Though the state boasts over 20 miles of ocean shoreline, Delaware is made up primarily of small to medium-sized towns. The most significant city is Wilmington with little more than 70,000 residents. However, the state’s beauty does attract more than its share of tourists during peak season, which helps keep the economy healthy.
Plus, according to Delaware Public Media, it is ranked the 6th most bicycle-friendly state in the US. So, if you are seeking to retire in a place you can enjoy exploring from behind your handlebars, Delaware is the place for you.
One of the most attractive aspects of retiring to Delaware and why it was in the top 10 states to retire to according to WalletHub, is because Delaware is affordable and one of the more tax-friendly states retirees can find:
- No Social Security tax
- No sales tax at the local or state level
- Has the 6th lowest property tax
- No estate or inheritance tax
- Withdrawals from retirement are only partially taxed
- Both public and private pension income is only partially taxed
- Offers up to $12,500 deduction on income from retirement or pension savings accounts, such as 401Ks and IRAs
In addition to being a tax-friendly state, Delaware also ranks 32nd for the lowest cost of living. So for retirees looking for a laid back place to live with ample opportunities to stay active, Delaware should be at the top of your list.

Places to Retire in Delaware
- Wilmington
- New Castle
- Millsboro
- Lewes
- Rehoboth Beach
Wilmington

- Percent of Senior Population: 13%
- Overall Population: 70,139
Wilmington, the biggest city in Delaware, is located along the Delaware River. It is home to Goldey-Beacom College, Delaware College of Art and Design, and Widener University, all of which add to the city’s culture as well as influencing the art and theater communities.
Retirees looking to live in the city and stay active may want to consider renting or buying a condo along the river. Wilmington’s Riverwalk area is lined with new shops, apartments, and restaurants, bringing vibrancy back to the community.

The city is home to nine unique historic districts showcasing a variety of cultural resources and historical sites and buildings. And scattered amongst these areas are 55 parks, plus the riverwalk making Wilmington a very pedestrian and bicycle-friendly city.
Though the majority of the state enjoys mild winters, Wilmington does see snowstorms from time to time. But for the most part, the winters are mild compared to some of the areas north of Delaware. The summers average the mid-seventies but can get as hot as 90+.
One of the most significant aspects of Wilmington is the cultural diversity, which is celebrated during the many festivals hosted by the city. Some of the events include the Greek, Polish, African American, and Hispanic celebrations. Wilmington also boasts music festivals throughout the summer, including the Clifford Brown Jazz Festival and Riverfront Blues Festival, both of which are huge events bringing guests in from all over the state.
The biggest drawback for Wilmington is their crime rate, which is higher than the national average; however, the city is making great efforts to improve and make it a safer environment.
New Castle

- Percent of Senior Population: 19%
- Overall Population: 5,493
The quiet town of New Castle has an abundance of historical sites, including homes, libraries, and churches. Plus, it is home to several museums including:
- Old Library Museum full of vintage books
- Velocipede Museum – Featuring antique bicycles, tricycles, and more
- Dutch House Museum – Built in the 17th Century and managed by the historical society
- New Castle Court House Museum – Take a guided tour to learn about the first courthouse in Delaware
- Delaware Contemporary Museum – Filled with works created by local artists
And history buffs will love A Day in Olde New Castle. According to Wilmington and Brandywine Valley, it is “the country’s oldest continuous house and garden tour.” Homeowners and volunteers even dress up in colonial attire to welcome guests and give tours. A Day in Olde New Castle is held every spring in May.

Plus, New Castle hosts an array of festivals and outdoor concerts such as:
- Tall Ships
- Weekly summer concerts in the park
- Outdoor Antique Show
- Art on the Green
- Rivertowns Ride and Festival – One day ride two town festival between New Castle and Delaware City
And when your in the mood to visit a larger city, New Castle is located just:
- 15 Minutes from Wilmington
- 45 Minutes from Philadelphia
- 1 Hour from Baltimore
- 2 Hours from New York
The convenience of getting these larger cities makes New Castle the perfect place for retirees looking for small-town living with all of the comforts and luxuries of large cities.
Millsboro

- Percent of Senior Population: 19%
- Overall Population: 4,626
Millsboro is another historic town in Delaware, which gained its initial fame as a central point and economic hub for local communities. The city earned its notoriety as a commercial hub because it sits at the top of the river. Its location made it the ideal place for the dam as well as being the perfect location for the railroad. Millsboro built its railroad station shortly after the civil war, giving the town an extra economic boost.
Due to its rich history, Millsboro is also home to multiple museums and historical sites. Plus, it has several community theaters and art galleries. And if you are interested in shopping, Millsboro has specialty and boutique retail stores, but also in nearby Rehoboth, there are 140 outlet shops.

Outdoor enthusiasts looking to retire near the ocean but without the oceanfront prices will love Millsboro. The cost of housing is significantly less here than what residents find 30 minutes away on the coast. And though Millsboro isn’t on the ocean, it is on the Indian River, providing ample opportunities to get out and enjoy the water.
Plus, Millsboro offers several golf courses and city parks to stay active during the warmer seasons. Though the climate here is mild most of the year, winter temperatures can get into the 20s with warmer summers reaching into the mid-80s.
Lewes

- Percent of Senior Population: 49%
- Overall Population: 3,353
Though Lewes has a small population, peak tourist season can host more than 10,000 people. However, one of the reasons retirees find Lewes so attractive is that during the off-season, they get to enjoy this beautiful small town all to themselves.
Lewes’ retirement population has grown substantially over recent years and is now up to almost 50% of the population, making the city all the more appealing to seniors looking to enjoy time with other retirees.

Lewes is the ideal place for those looking to spend the better part of their retirement enjoying the outdoors. Not only is the ocean available for boating, kayaking, and swimming, but there are also plenty of parks in and around the city perfect for walking, hiking, and biking.
Another very appealing aspect of Lewes is the weather. This oceanfront community enjoys warm summers and mild winters allowing the residents to enjoy outdoor activities year-round.
And if all of that is not appealing enough for you to consider retiring here, then maybe the fact that Lewes is home to the second-highest ranked hospital, Beebe Healthcare, in the state. There are also numerous medical centers, for specialties such as:
- Cardiac
- Vascular
- Women’s health
- Chronic diseases and management
Rehoboth Beach

Ever wanted to retire to a dream vacation spot? Well, you are not alone; the population in Rehoboth Beach is made up of more than 40% of retirees. Plus, Rehoboth Beach is a very diverse community, making all feel welcome. Much like Lewes, Rehoboth Beach fills up with tourists flocking in from DC during peak season, but the rest of the year is much quieter.
Rehoboth Beach is a very walkable oceanside town, so for those looking to ditch their cars for a healthier retirement lifestyle, this is the town for you. It is home to a mile-long boardwalk dotted with hotels, boutiques, and restaurants. Miles of open beaches, and when you need to stock up on food, they even host the Rehoboth Beach Farmer’s Market.

Plus, much like the rest of Delaware, it is easy to escape to a variety of cities for the day or weekend, including DC, Philadelphia, Wilmington, and Baltimore, all of which are only a 2-3 hour drive from the beach.
This town also hosts a few different fun events such as the annual chocolate festival, craft and art shows, golf tournaments, and more. Though you aren’t going to see a broadway play here or go to the symphony, Rehoboth Beach has more than enough going to keep any retiree busy.
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