The Chesapeake Bay's 7 Best Retirement Towns Ranked
The Chesapeake Bay is the largest estuary in the United States. Its region spans 64,000 square miles and is home to more than 17 million people. While half of the water in the bay comes from the Atlantic Ocean, the rest is fed from a watershed extending 524 miles from Cooperstown, New York, to Norfolk, Virginia. Within the Chesapeake Bay region, there are some truly delightful towns in which to retire. The seven towns described below are listed among the best retirement towns in the Chesapeake Bay based on their population, affordability, percentage of seniors living there, abundance of things to do, proximity to good health care, and more.
Lewes, Delaware
First on our list is the town of Lewes, in southern Delaware, Sussex County. Per the US Census Bureau, 3,604 people live in Lewes as of 2023, and more than half of them are over the age of 65. Lewes is a quiet, peaceful, serene beach town that has quickly become a popular retirement destination, partly due to its proximity to larger cities. Lewes is just 110 miles from both Baltimore, Maryland, and Philadelphia, Pennsylvania. Although living in Lewes might not be as cost-effective as in some other towns (according to Zillow.com, the median home value in Lewes is $581,000), if you can afford to live there, Lewes provides retirees with a tranquil, fulfilled way of life.
Natural beauty surrounds the easily walkable town of Lewes, with its position along the Delaware Bay, connected to the Chesapeake Bay through the Intracoastal Waterway and the Chesapeake & Delaware (C&D) Canal. Cape Henlopen State Park is perfect for outdoor lovers, with its 18-hole disc golf course, walking trails, basketball courts, beaches, and camping area. The Cape May-Lewes Ferry also provides convenient, leisurely transportation across the bay to New Jersey. Public transportation is available through the DART First State service, operating local routes, intercounty routes, and a beach bus with service to beaches running south all the way to Ocean City, Maryland. The Lewes Senior Activity Center on Janice Road offers socialization and activities for those aged 50 and up. When medical care is needed, the Beebe Healthcare System's Level III trauma center in Lewes fits the bill.
Mathews, Virginia
Part of the Virginia Beach metropolitan area, Mathews, Virginia, is the county seat of Mathews County and is home to 1,145 people, with almost 33% aged 65 and over. Established around 1700, this small town is about 75 miles from Richmond, Virginia, and 66 miles from Norfolk, Virginia. No stoplights exist in this tiny, historic town. The slower pace of life, along with its relative affordability (with home values averaging $445,000), proximity to both the Chesapeake and Mobjack Bays and endless beauty all add up to make Mathews a great place to retire.
The downtown area of Mathews includes antique stores such as Doodlebugs, art spaces like Art Speaks Gallery, and restaurants including Richardson's Cafe. The Mathews Farmers Market is held on the Historic Courthouse Green every Saturday from April through October. The Mathews Active Lifestyle Center on Buckley Hall Road provides programs and activities for seniors with no age requirements. Primary medical care is available at Riverside Mathews Medical Center clinic, with the larger Riverside Walter Reed Hospital in Gloucester just 20 minutes away. Public transportation needs are met through Bay Transit, serving the Northern Neck and Middle Peninsula region, including Mathews County.
Chesapeake City, Maryland
The only town in Maryland situated on a working commercial canal, Chesapeake City, in Cecil County, marks an area where the Chesapeake Bay is connected with the Delaware River. This historic town, dating to 1824, is home to 746 people today, with almost 28% of them being over age 65. One of the highlights of living in Chesapeake City is seeing the cargo ships, tugboats, and other vessels traveling through the C&D Canal and under the 140-foot-high Chesapeake City Bridge each day. Home values here average $398,000, and both Baltimore, Maryland and Philadelphia, Pennsylvania are just an hour away. These are all reasons why many are choosing to retire to Chesapeake City.
Chesapeake City's historic area is on the National Historic Registry and Maryland's historic registry and consists of restored historic homes, shops like The Old Gray Mare Gift Shop, and art galleries such as Chesapeake City Arts. The charming waterfront park, Pell Gardens, is a great place to relax and listen to the free concerts provided there each summer. If seniors are looking for opportunities to socialize with other seniors, they may opt to visit the Elkton Senior Activities Center in Elkton, just six miles north of Chesapeake City. Public transportation to other parts of Cecil County, as well as to New Castle County, Delaware, and Harford County, Maryland, is provided by Cecil Transit bus service. Medical care can also be found in nearby Elkton at Christiana Care Union Hospital.
Easton, Maryland
On the Chesapeake Bay's eastern shore, near the head of the Tred Avon River, sits the town of Easton, Maryland. Established in 1710 as the county seat of Talbot County, Easton is home to 17,225 folks, with over a quarter of them aged 65 and up. Easton is about an hour and a half from both Baltimore, Maryland, and Washington D.C., and less than an hour from the state capital of Annapolis, Maryland. Median home values in Easton are $431,000. Its heritage, affordability, natural beauty, and cultural attractions all draw many retirees to consider Easton as their new home.
A mixture of history and natural beauty is found in the Talbot Historical Society Gardens in Easton's downtown area, amid the many historical buildings surrounding it. Cultural events abound in Easton, including the Chesapeake Chamber Music Festival, which is held each June at the Avalon Theatre. The annual Waterfowl Festival also draws tens of thousands to Easton to view wildlife art and participate in conservation awareness efforts. Seniors wishing to interact with their age group may do so at the Brookletts Place, Talbot County Senior Center on Brookletts Avenue, which offers services for ages 60 and up. Top-notch medical care is found at the University of Maryland Shore Medical Center in Easton. While the town of Easton does not offer public transportation, Delmarva Community Transit provides public transit service through the Mid and Upper Eastern Shore areas.
Poquoson, Virginia
Also known as Bull Island (in recognition of the town's farmers who used to let cattle roam free in the salt marshes), the independent town of Poquoson, Virginia, of no county, is home to 12,635 people, almost 20% of whom are over age 65. Bloomberg Business Week ranked Poquoson as the "Number 1 Suburb in Virginia," and it was named the eighth healthiest locality in Virginia by the Population Health Institute. The oldest continuously named city in Virginia, Poquoson, was established in 1631 on the Virginia Peninsula of the Chesapeake Bay. Combined with median home values of $437,000, all of these factors make Poquoson an ideal Chesapeake Bay retirement destination.
Poquoson has a real small-town, community-oriented feel, with many recreational opportunities for all ages. These include the Poquoson Municipal Pool, Poquoson Community Center, boating and paddling on the Poquoson River and Back River, and experiencing the beautiful Whitehouse Cove Marina with its delectable Surf Rider Restaurant. The Poquoson Senior Center on Poquoson Avenue caters to those aged 60 and over. Poquoson does not have its own public transportation system but is served by Hampton Roads Transit. Medical care can be sought at Riverside Regional Medical Center in Newport News, just nine miles away.
Berlin, Maryland
The small coastal town of Berlin, in Worcester County, Maryland, was named one of America's Coolest Small Towns by Budget Travel magazine. With a population of 5,346, almost 19% of whom are over 65, some are surprised to find that two movies, "Runaway Bride" and "Tuck, Everlasting," have been filmed in this tiny town. Median home values here are $439,000. Just nine miles from the busier beach town of Ocean City, Maryland, and 111 miles from Maryland's capital city of Annapolis, Maryland, Berlin's village-style atmosphere and affordability have attracted many retirees to move here.
Berlin's history, dating to 1677, and the arts are both important components to understanding the town's appeal. Fifty buildings in this highly walkable town are on the National Register of Historic Places, including Burley Manor. Additionally, the Maryland State Arts Council designated Berlin as an Arts and Entertainment District, with many art installations, murals, and studios such as Jeffrey Auxer Glass Design Studio found in town. Berlin's Farmer's Market, held Sundays from May through September, brings the townsfolk together and entices visitors to sample local produce and wares. Seniors age 50 and up can get together at the Berlin 50Plus Center on Old Ocean City Boulevard. Medical care is available when needed at Berlin's Atlantic General Hospital. The Shore Transit system provides public transportation throughout Somerset, Wicomico, and Worcester Counties, including Berlin.
Havre de Grace, Maryland
Last but certainly not least on our list of the best Chesapeake Bay towns in which to retire is Havre de Grace, in Harford County, Maryland. This town, whose name means "port of grace," sits at the mouth of the Susquehanna River and the head of the Chesapeake Bay. Of its 15,032 townsfolk, 18% are age 65 or older. Median home values here are $450,000. Havre de Grace is just 40 miles from Baltimore, Maryland, and 50 miles from Philadelphia, Pennsylvania, making it the perfect suburban town for retirees who want to experience living in solitude on the bay yet remain close to larger-city amenities.
One unique Havre de Grace feature is its quarter-mile-long promenade, running along the Susquehanna River and near popular town landmarks such as the Maritime Museum, Decoy Museum, and Concord Point Lighthouse. Fishing and boating on the Susquehanna River are also favorite pastimes in Havre de Grace, with pike, perch, and bass often seen leaping from the water. The Havre de Grace Senior Activity Center on Lewis Lane provides activities, programs, and services for the town's senior population. Stellar medical care is just 15 miles away in nearby Bel Air, at the University of Maryland Upper Chesapeake Medical Center. The Harford Transit LINK bus service serves the public transportation needs of Havre de Grace and other Harford County towns.
The Chesapeake Bay region has become a popular retirement destination due to its temperate climate, affordable cost of living, boundless cultural attractions, and access to first-rate healthcare. Living amongst a vital ecosystem with more than 3,600 species of plants and animals appeals to nature lovers and those who cherish the environment. Choosing to retire in any of the seven towns listed above will ensure that the evening of your life is secure, stable, fulfilling, and enjoyable.
