8 Under-The-Radar Retirement Towns In Maryland

Maryland has great health care, really nice people, fast internet speeds (it ranks at or near the top in that regard, according to multiple sources), and a wide variety of things to do and see. Furthermore, the weather is not brutal, with areas closer to the Bay tending to have milder winters and cooler summers. Although many people seek out well-known spots to plant their roots, several under-the-radar locations in Maryland also offer a great bang for the buck. Not sure where to look? Starting with Chestertown, discover eight under-the-radar retirement towns in Maryland.

Chestertown

Chestertown is a small historic river town on the Eastern Shore, loved for its Colonial charm, walkable downtown, and placid, pastoral environment. The best part about retiring in Chestertown is that Columbia is within 80 minutes, and houses fetch a median listing price of $391,167, which is slightly below the statewide median of $408,000.

The University of Maryland Shore Medical Center, honored by the Maryland Rural Health Association (MRHA) as a recipient of its 2024 Outstanding Rural Health Program Award, is at your doorstep. Golfers have access to Chester River Yacht & Country Club, which features a nice layout with subtle undulations. Washington College, which is one of the oldest colleges in the US, offers a burst of youthful energy and academic opportunities, while the Garfield Center for the Arts at the Prince Theatre is a nice place to enjoy a show.

Easton

Just about 45 minutes south of Chestertown, Easton scores big on culture, walkability, and quality of life. This bustling community is widely regarded as the cultural capital of the Eastern Shore and has a lively arts scene, especially for a town of its size. The historic Avalon Theatre, which boasts a rare five stars on Google Reviews, often hosts concerts, film screenings, and stage performances throughout the year. Similarly, the Academy Art Museum, in a circa-1820s building, offers rotating exhibitions and classes, drawing art lovers from the region.

Also, fun-filled annual events like the Waterfowl Festival, always held the second full weekend in November, and Plein Air Easton, the largest and most prestigious juried plein air painting competition in the United States, bring thousands of visitors who come to celebrate wildlife art, conservation, and creative expression. In terms of healthcare access, University of Maryland Shore Regional Health (UM SRH) is the principal provider of comprehensive healthcare services to more than 170,000 residents of five counties on Maryland’s Eastern Shore.

Cambridge

Cambridge gets the spotlight because of its awesome affordability. Houses in Cambridge fetch a median listing price of $319,233, which is way below the statewide median. But it is not all about affordability. Cambridge itself is a neat waterfront town with a quiet pace and a community feel. River Marsh Golf Club, a well-known recreational hub, boasts a beautiful, challenging course in pretty good shape.

Blackwater National Wildlife Refuge, a beautiful spot to see eagles wheeling overhead, offers terrific views, well-maintained trails, and a variety of shorebirds. There's the Cambridge Premium Cinemas, loved for its comfortable recliners, unbeatable price points, and good sound system. With its benches and swings, Gerry Boyle Park at Great Marsh is a beautiful space for a quick walk, fishing, a picnic, or watching sunrises or sunsets.

Thurmont

Thurmont is a renowned mountain-gateway town noted for nature and outdoor amenities. It sits at the eastern foothill of the Catoctin spur of the Blue Ridge Mountains, an area with beautiful scenery and forested ridges, making it a natural transition point between rural Maryland and the Appalachian highlands. Residents have access to the Catoctin National Recreation Trail, which runs 26.6 miles along the easternmost ridge of the Blue Ridge Mountains.

They also have easy access to three awesome outdoor venues: Catoctin Mountain Park, Cunningham Falls State Park, and Gambrill State Park, which is a scenic expanse with lovely trails for hiking and biking. There's Frederick Health, which has previously received the America's 100 Best Hospitals Award for three consecutive years. Keep in mind that Mount St. Mary's University is in nearby Emmitsburg and is famous as the second-oldest Catholic university in the US.

Berlin

Berlin gets a shout-out because of its proximity to the ocean, and, hence, the many sandy beaches dotting the coastal strip, especially around Ocean City, which is just eight miles east. Ocean City has a modern boardwalk, Ocean City Beach, which offers all kinds of exciting activities under the sun, and a reputation for some of the best marlin fishing in America. Atlantic General Hospital Corporation, which serves largely rural Worcester County, was recently recognized by the Association of periOperative Registered Nurses (AORN) as a Center of Excellence in Surgical Safety, especially for effectively eliminating the hazards of surgical smoke.

The cherry on top is that Berlin and the surrounding area have several highly rated golf options. These include Eagle’s Landing Golf Course, named the Number One Golf Course in Maryland by Golfers’ Choice for 2021. It is a seaside golfing paradise that offers sweeping views of the bay. Assateague State Park, famous for its beaches, wild ponies, fishing, kayaking, hiking, and wildlife viewing, is minutes from Berlin and is one of the area’s best outdoor adventure spots.

Sykesville

There are several pleasant things about Sykesville; however, one of the aspects you will love most about it is its fantastic proximity to Baltimore, which is just 30 minutes down the road. That said, Sykesville itself is a charming small town with parks and a rich history. You will find brick sidewalks, restored 19th-century buildings, and outdoor recreational opportunities at places like the nearby Morgan Run Natural Environmental Area, which offers hiking, horseback riding, and birdwatching.

Other notable outdoor venues include Piney Run Park, which features a 300-acre lake and over five miles of beautiful trails to explore. Carroll Hospital Centre, a 20-minute drive, has been recognized by Healthgrades with the Outpatient Prostate Care Excellence Award and the America's 100 Best Hospitals for Prostate Surgery Award. McDaniel College, also in Westminster, is a small liberal arts college with a variety of academic programs.

Saint Michaels

Saint Michaels is a postcard-perfect harbor town that offers a serene retirement experience, quiet charm, and rich maritime history. One of the town's outdoor landmarks is The Links at Perry Cabin, a premier golf destination designed by the legendary Pete Dye, an outdoor beauty that provides breathtaking views of the Miles River and Chesapeake Bay. Talking of rivers and bays, water lovers at Saint Michaels here will be spoiled for choice because there are plentiful boating and paddling opportunities.

Cultural attractions include the centrally located Chesapeake Bay Maritime Museum, the only museum devoted to interpreting the entire maritime region of the Chesapeake. Meanwhile, Saint Michaels Museum features regional history exhibits, while Classic Motor Museum of Saint Michaels displays interesting classic cars. For more amenities, including hospitals, Easton is 10 miles to the east.

Cumberland

With its gorgeous rolling hills and classical architecture dating back to the Colonial era, Cumberland is among the most picturesque and culturally vibrant places to retire. You will find some of the quirkiest museums around, fantastic local wineries, and the Great Allegheny Passage, which offers 150 miles of spectacular biking and hiking from Cumberland to Pittsburgh through Pennsylvania's Laurel Highlands. There's also the chance to experience art at the F. Brooke Whiting House & Museum, which displays pieces from around the world.

UPMC Western Maryland, the main acute‑care hospital serving Cumberland and the surrounding region, has bagged several awards from Healthgrades, including Surgical Care Excellence Award, America’s 100 Best Hospitals for Spine Surgery Award, and Cardiac Surgery Excellence Award. Meanwhile, golfers have the Jack Nicklaus signature course at Rocky Gap State Park, which offers one of the region’s most scenic golf experiences. It holds the distinction of being Maryland's only Jack Nicklaus Design.

So, if you’ve chosen to retire in Maryland, it pays to look beyond the usual headline towns with long-established reputations. Tucked quietly in plain sight are several outstanding communities that offer the same high-quality amenities and everyday comforts, often without the premium price tag. Because these destinations remain under the radar, they tend to attract less competition, helping keep living costs more reasonable while still delivering an exceptional quality of life.