Delaware is the second smallest state, but it’s got a lot to offer! With a rich history dating back to the 1700s, this tiny state was the first of the original thirteen colonies to ratify the Constitution. Thomas Jefferson once referred to Delaware a “jewel among states” due to its beauty and significance. Today, Delaware is better known as the “Home of Tax Free Shopping”; it’s one of only five states without sales tax. According to a study done by Wallethub, Delaware ranks as the fourth best state for retirement.
So, why are so many older adults choosing to retire in Delaware? It could be the low crime rates and lower cost of living. It could be the ideal location. Or it could be the charming small towns that are perfect for a weekend escape or an extended stay. Read on to learn more about the best places in Delaware for retirement.

Bridgeville
With just over 3,000 residents, Bridgeville is the quintessential small town. The tight-knit community is actually the oldest in Sussex County. This town was named for the bridge that was built across a stream and still serves as the center of the city. Punkin Chunkin, a popular pumpkin-throwing contest and fall festival, draws a flock of tourists to Bridgeville every autumn.
Fenwick Island
Known as the “Quiet Resort,” this small coastal town is known for its fishing, watersports, and beautiful white sand beaches. Once a haven for pirates and sailors, Fenwick Island is now a popular vacation spot beloved by tourists of all ages. The DiscoverSea Shipwreck Museum showcases over 10,000 maritime artifacts. In keeping with Fenwick Island’s naval history, the Fenwick Island Lighthouse is a dual lighthouse and museum that’s open to visitors year-round!
Georgetown
This small town has both charm and history in spades! The Marvel Carriage Museum displays a unique collection of carriages and artifacts related to Georgetown’s history. Located in the heart of town is St. Paul’s Episcopal Church, the oldest church in Georgetown. It’s open to both worshippers and those eager to examine the true Victorian Gothic architecture.

Lewes
Hailed as the “First Town in the First State”, Lewes takes pride in its nautical heritage. Within the historic district, there are numerous museums, antique shops, and restaurants. This beach town is nestled along the Delaware Bay, providing plenty of fishing opportunities for anglers. Sailboats and kayaks are always available to rent. Every April, the Lewes Tulip Celebration celebrates the town’s Dutch heritage by way of walking tours, floral demonstrations, and art exhibits.
Magnolia
Magnolia is a small town with a lot of heart! The tight-knit community is home to a little over 300 residents. The town houses two popular local establishments: Magnolia Furniture and Magnolia Family Restaurant. Magnolia is also home to Jonathan’s Landing, an 18-hole championship golf course with a full driving range and practice green.

New Castle
This picturesque town was the filming location for Robin Williams’ beloved 1989 film “Dead Poets Society.” The Old Dutch House, now a museum and gardens, is the second oldest structure in Delaware. Battery Park offers beautiful riverfront views and plenty of recreational opportunities.
Rehoboth Beach
Affectionately nicknamed “The Nation’s Summer Capital”, Rehoboth Beach is a great place to visit or call home. The famous boardwalk features an eclectic mixture of shops, restaurants, and amusement park rides. Cape Henlopen State Park features walking trails, an educational nature center, and historic Fort Miles. Over 200,000 people attend the Sea Witch Halloween Festival every October.
55 Plus Communities in Delaware
The Ponds at Bayberry is a luxury 55+ active adult community in Middletown, Delaware. This community offers single-family and villa homes and maintenance-free living. The 10,000 square foot clubhouse and social center is the perfect place to meet friends, play cards, and get your sweat on. Relax by the pool or grab a drink from the self-service tiki bar. This is resort-style living at its finest!
More Delaware Resources
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Robert Fowler
Contributing WriterRobert Fowler is a retired blogger who lives with his wife, Mary Ann at Village at Deaton Creek, a Del Webb Community in North Georgia. Robert was previously the President of Retirement Media Inc. He has visited numerous 55+ Active Adult Communities over the years, sharing his experiences along the way with readers. View more posts