WineFest in St. Michaels, Maryland with busy downtown streets. Image credit tokar via Shutterstock

6 Towns Perfect for Retirement on the Chesapeake Bay

Spending the golden years in the Chesapeake Bay area offers many benefits to retirees, including joining a welcoming and close-knit atmosphere with friendly neighbors and a strong sense of community spirit. The region is home to numerous top-notch healthcare facilities and affordable homes where retirees can find various housing options to fit their budget, including waterfront homes, historic properties, and retirement communities. Moreover, the overall cost of living in many Chesapeake Bay towns is relatively affordable compared to other coastal regions. So maybe it’s time to take a closer look at towns in Maryland like Annapolis, Easton, Cambridge, St. Michaels, Chestertown, or Mathews, Virginia.

Annapolis, Maryland

The people and traffic in the main street of Annapolis, Maryland.
Main street of Annapolis, Maryland. Image credit Wirestock Creators via

The capital of Maryland, Annapolis, is an ideal destination for retirees who want to spend an active and fulfilling retirement in a picturesque town with a waterfront, historical sites, and a wide range of cultural attractions. Known as the “Sailing Capital of the US,” Annapolis is the perfect place for senior sailors to drop anchor and explore the Annapolis Maritime Museum to learn about the area’s maritime heritage or take a guided walking tour of the United States Naval Academy and see the historic landmarks like Bancroft Hall and the Naval Academy Chapel. Annapolis's City Dock is a bustling waterfront area where retirees can stroll along the promenade, watch sailboats gliding by, and dine at waterfront restaurants offering famous Maryland blue crab like the Boatyard Bar & Grill, Cantler’s Riverside Inn, or The Chop Tank.

The median sale price of $650,000 (according to in early 2024 was higher than the US average price of $400,000. If owning a new home isn’t in the budget, there are several 55+ housing communities in Annapolis, which means enjoying maintenance-free homes, security, community clubs, and more, including Heritage Harbour, The Hamlets at South River Colony, and the newly constructed The Element at Mill Creek.

Easton, Maryland

Thompson Park and the historic City center of Easton, Maryland.
Thompson Park and the historic City center of Easton, Maryland. Image credit grandbrothers via Shutterstock

About 70 miles east of Washington, DC, on Maryland’s Eastern Shore, Easton is a small seaside town of around 17,500 residents. Buzzing with creative energy and a vibrant arts scene, art lovers of all ages will enjoy strolling along its iconic brick sidewalks, exploring the Academy Art Museum with a free docent tour, and attending performances at the historic Avalon Theatre. In 2024, Easton was named AFAR Magazine’s “Most Charming Small Town in Maryland” partly due to its stately architecture mixed with forward-looking energy. Efforts to revitalize the city a few years ago have certainly paid off with the arrival of restaurants like the 2024 James Beard Foundation Nominee, Bas Rouge—a contemporary European restaurant with a world-class wine list. Retired foodies will love The Wardroom, an epicurean market featuring artisanal products, cold-pressed juice shop Bumble Bee Juice, and Bonheur Pie and Ice Cream for that afternoon sweet treat.

Easton offers relatively affordable housing options compared to nearby waterfront communities with a median home price of around $475,000. The University of Maryland Shore Medical Center at Easton provides excellent healthcare services, including a regular “Don’t Worry, Be Healthy” workshop with topics designed to teach participants how to make healthier choices.

Cambridge, Maryland

The lighthouse and marina at Cambridge, Maryland.
The lighthouse and marina at Cambridge, Maryland.

With around 13,000 residents, Cambridge attracts retired outdoor enthusiasts, birds, boaters, and anglers drawn by its relaxed pace of life, waterfront views, and outdoor recreation opportunities. The 30,000-acre Blackwater Wildlife Refuge, named by USA Today as one of the ten best spots to view wildlife, is home to over 250 species of birds and is one of the main wintering areas for migratory ducks and Canadian geese. The 4-mile-long Wildlife Drive through the refuge can be accessed by car, bike, or on foot. Bring binoculars and be on the lookout for bald eagles, great blue herons, and egrets.

History buffs with newfound time on their hands can follow in the footsteps of American hero Harriet Tubman along the Harriet Tubman Underground Scenic Byway, the secret network of trails, waterways, and safe houses used by enslaved people heading north to escape slavery. Or check out the Richardson Maritime Museum in town.

Median home listing prices in and around the Cambridge area are $289,000, much lower than the US average price, particularly inland from the waterfront.

Chestertown, Maryland

The charming business district in Chestertown, Maryland.
Downtown street in Chestertown, Maryland. Image credit George Sheldon via Shutterstock

With a median home listing price of $415,000, but a much lower median home sold price of $265,000 (in early 2024), colonial Chestertown is an excellent choice for empty nesters looking for affordable housing in a small, dog-friendly community. Along with its very own dog park, many of Chestertown’s restaurants welcome four-legged visitors on their outdoor patios, and the Chestertown Famers Market invites well-behaved pooches to their year-round artisanal market held every Saturday morning. The University of Maryland Shore Medical Center at Chestertown helps Chestertown’s seniors stay healthy. It is an accredited Level 3 Geriatric Emergency Department by the American College of Emergency Physicians.

To explore historic colonial Chestertown, the Historical Society of Kent County is a great source of information and provides a self-guided walking tour of the town with many plaques commemorating significant events, buildings, and individuals throughout its history, like Fountain Park, created by the Ladies Improvement Society, and whose current fountain dates back to 1899, the Gothic Christ Methodist Church and the White Swan Tavern built initially as a residence in 1733. Every year, Chestertown holds the two-day Chestertown Tea Party Festival, its very own version of the Boston Tea Party, with a street party, live music, a colonial parade, and a re-enactment of the original tea party.

St. Michaels, Maryland

Aerial view of Saint Michaels, Maryland.
Overlooking Saint Michaels, Maryland.

St. Michaels is a tranquil waterfront town known for its historic charm and scenic beauty. It is a prime destination for history buffs, outdoor enthusiasts, and wine lovers. Retirees can tour the St. Michaels Museum, housed inside a series of 19th-century buildings, to learn more about the town’s rich heritage or discover its history by boat. Patriot Cruises offers 70-minute narrated tours along the Miles River, where guests can see 200-year-old historic mansions, beautiful scenery, and wildlife like osprey and dolphins.

Wine collectors can replenish their cellars with any 18 wines available at St. Michaels Winery or join a tasting of dry-wine or sweet-wine flights or by the bottle. The Windon Distilling Company offers tastings of its small-batch Lyon Rum seven days a week.

St. Michaels is known for its higher cost of living. Still, it may be worth the price for financially stable retirees looking for a safe, walkable, peaceful waterfront community to spend their twilight years. The median listing home price sits just below 1 million in 2024, well above the US average.

Mathews, Virginia

An old T Bucket in the Annual Vintage TV's "Chasing Pavement Vintage Automotive Festival" in Mathews, Virginia.
An old T Bucket in the Annual Vintage TV's "Chasing Pavement Vintage Automotive Festival" in Mathews, Virginia. Image credit Barry Blackburn via

Mathews is a charming community with abundant coastal influences thanks to its proximity to Chesapeake and Mobjack Bays. Folks who retire to Mathews can’t get enough of its bays, rivers, and creeks. Mathews has two beaches within its borders—Haven Beach and Bethel Beach Natural Area Preserve, an 83-acre stretch of sandy beach, low dunes, and marshes on Chesapeake Bay. Active retirees can enjoy many water sports, from kayaking to stand-up paddle boarding and sailing.

The annual Mathews Market Days Festival, held on the weekend after Labor Day, celebrates Mathews' strong connection to its artistic and creative culture with over 50 art and craft vendors selling locally made, Chesapeake Bay-inspired items, jewelry, soaps, and more. It is held in the old court house square.

Home prices in Mathews are on par with the US average of $400,000. For healthcare, residents of the town look to Riverside Mathews Medical Center in downtown Mathews or at nearby Riverside Walter Reed Hospital in Gloucester.

Retiring in the Chesapeake Bay area offers golden agers many benefits, including a close-knit community, top-notch healthcare, and affordable housing options. Maryland’s capital city, Annapolis, boasts a vibrant waterfront and rich cultural heritage, while Easton’s thriving arts scene is a big plus. Cambridge boasts affordable housing options, while colonial Chestertown helps newcomers learn about the town’s history with guided maps and plaques. St. Michaels entices history buffs and wine lovers with its tranquil waterfront despite a higher cost of living. Finally, Mathews, Virginia, offers coastal living and artistic culture at an affordable price.

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