9 Best Towns In Maryland To Retire Comfortably
Many who reach retirement age are investigating spending their golden years in Maryland. The state does not tax Social Security income, and retirees also benefit from its relatively mild climate, proximity to both the ocean and mountains, and access to high-quality healthcare systems. Other advantages of retiring to Maryland include its natural scenic beauty, rich historical attractions, and relaxed way of life. These nine smaller towns, all with populations under 50,000, are perfect for a comfortable retirement. Each one, from the riverside calm of Port Deposit to the cultural pull of Cambridge and the mountain quiet of Oakland, offers a distinct setting for peaceful and fulfilling senior living.
Crisfield
At the southernmost point in Maryland sits a small waterfront community well suited to an easygoing retirement. The village, founded in 1666, is known as the "Crab Capital of the World," and its identity is still tied to the water and to the seafood trade that built it. The town entices retirees with its close-knit atmosphere, particularly its many annual events that create shared town pride, such as the J. Millard Tawes Crab and Clam Bake each September. Active seniors will also appreciate Crisfield's natural setting, with nearby Janes Island State Park housing a variety of wildlife, including crabs, birds, and fish, along with quiet water trails for paddling.
Shore Transit provides public transportation to Crisfield residents, making it easy to get around. For medical care, TidalHealth McCready Pavilion in Crisfield offers emergency care, outpatient care, and diagnostic services. If retirement living needs should arise, the Alice B. Tawes Nursing & Rehabilitation Center provides skilled nursing care, and Chesapeake Cove Assisted Living accommodates those requiring less help.
Chesapeake City
Chesapeake City is more than just a small town under a 4,000-foot-long bridge. This village in Cecil County, with less than a thousand residents, sits on the Chesapeake and Delaware Canal. It may be tiny, but it is beautiful, mighty, and welcoming to all. The waterside setting and the slow rhythm of canal traffic are a big part of why many retirees settle here.
The streets of Chesapeake City are filled with historic buildings from the 19th century that, today, house independent shops such as Chick's and The Mercantile at Back Creek. Along the waterfront, Pell Gardens is a small park that often hosts live music in the summer months. Cecil Transit serves Chesapeake City with scheduled demand public transit service on the first Wednesday of the month. The nearest hospital, Christiana Care at Union Hospital, is just six miles north of town, in Elkton. Meanwhile, Well Homed Assisted Living in Elkton, nine miles up the road, can give medical care and housing if needed.
Hyattsville
Just seven miles from Washington, DC, the town of Hyattsville, in Prince George's County, houses just over 20,600 residents, 10% of whom are over age 65. Many retirees appreciate Hyattsville's placement close to our nation's capital while still retaining its smaller-town, suburban atmosphere. As the town's motto states, "The world is within walking distance," and the walkable layout, arts district, and easy transit access are what tend to draw retirees here.
Hyattsville residents have easy access to two metro stations, putting them within DC or other nearby towns in just minutes. Two community gardens and around a dozen parks provide ample outdoor recreational opportunities for all residents, including seniors. Tree-lined streets and a multitude of services for seniors create a welcoming atmosphere for retirees. They include Call-a-Bus service, aimed at providing seniors and people with disabilities easy transportation to medical appointments, stores, pharmacies, and more for free. If you do take the service for medical care, head to Luminis Health Doctors Community Hospital, a 330-bed facility. Many retirement living options exist, such as Independence Court of Hyattsville for assisted living, and Complete Care at Hyattsville for continuing care services.
Boonsboro
A small town in Washington County, at the foot of South Mountain, Boonsboro is home to almost 4,000 residents. About 65 miles west of Baltimore, this historical mountain town, founded in 1792, draws retirees with its quiet pace and its setting against the ridgeline. It is also a safe community, with only one violent crime in 2019, according to FBI data. Healthcare is covered as well, as the closest hospital is Meritus Medical Center in Hagerstown, just 10 miles north of Boonsboro. Should extra care be needed during retirement years, Sterling Care South Mountain offers assisted living, and Fahrney Keedy Senior Living Community in Hagerstown supplies levels of continuing care.
Outdoor lovers praise Boonsboro's beauty and quietude and enjoy spending time in Washington Monument State Park at the summit of South Mountain's Monument Knob. The park contains the Washington Monument, a 30-foot-high stone tower that was the first completed monument to George Washington. Nearby, Greenbrier State Park hosts a 42-acre man-made lake ideal for fishing, boating, and swimming.
Cumberland
A truly historic town sitting in an Allegany County valley formed by the North Branch of the Potomac River and Wills Creek, Cumberland is surrounded by the Appalachian Mountains. It lies two hours southeast of Pittsburgh, Pennsylvania. Almost a quarter of Cumberland's population is over age 65, and the town has long been a comfortable base for retirees drawn to its mountain surroundings. Once the second largest town in the state, Cumberland, founded in 1787, has retained its nickname of "Queen City." Today, its historic buildings house boutiques like Buttercup Boutique, art galleries such as Gilchrist Gallery, and eateries including Ristorante Ottaviani.
The Allegany County Transit Authority provides public transportation services to Cumberland. Moreover, UPMC Western Maryland, an affiliate of the University of Pittsburgh Medical Center, is a top-notch hospital located right in town. Many retirement options are available in Cumberland, including Chamberlain Graceful Living with assisted living and Mountain View independent living senior apartments. For active retirees, the Great Allegheny Passage trailhead in town offers miles of level walking and cycling along the old rail corridor.
Port Deposit
Port Deposit, in Cecil County, is home to just over 600 residents, making it one of Maryland's smallest communities. This small town along the Susquehanna River is an ideal calm setting for seniors longing for quiet and natural beauty during their retirement years. The Elkton Senior Activity Center, about 20 miles east of town, offers seniors opportunities for social connection and educational programs. Marina Park, within Port Deposit, hosts many activities seniors may enjoy, such as a Farmers Market on the second Saturdays from June through October, with the river and the historic granite buildings of Main Street as a backdrop.
When it comes to retirement, healthcare is a major concern, and while Port Deposit does not have a large medical center, services are not far away. The nearest hospital to town is the University of Maryland Upper Chesapeake Medical Center in Aberdeen, about 20 miles southwest of Port Deposit. For those who need regular assistance, Always There Assisted Living in Port Deposit is available with dedicated staff and plenty of amenities.
Cambridge
In Dorchester County on the Choptank River is the small town of Cambridge. With a population just over 13,000, of which 20% are over age 65, there is a lively social environment for seniors. Cambridge rewards a slower, water-oriented retirement, with friendly, walkable streets and boatable waters along one of the Eastern Shore's widest rivers. Art lovers won't want to miss the Dorchester County Center for the Arts in Cambridge, providing programming in the visual, musical, literary, and performing arts.
Delmarva Community Transit provides fixed-route and door-to-door public transportation to seniors in the town. For healthcare concerns, the University of Maryland Shore Regional Health at Cambridge offers diagnostic and therapeutic services, including emergency care, if needed. Mallard Bay Nursing and Rehab and Autumn Lake Healthcare at Chesapeake Woods, both in Cambridge, meet the needs for more skilled nursing care, if necessary.
Salisbury
Salisbury, the county seat of Wicomico County, blends small-town ease with convenient access to major East Coast cities. It has just over 33,000 residents, and about 13 percent are over the age of 65. Many retirees appreciate the location, as it sits just 45 minutes from Ocean City and within 150 miles of Baltimore, Washington, DC, and Philadelphia. This makes it ideal for visiting family, scheduling specialty appointments, or enjoying a quick trip to the beach.
The town's lively downtown offers shops like The Country House, art galleries such as Salisbury Art Space, and local eateries including MoJo's Urban Eatery. Public transportation is provided through Shore Transit, and TidalHealth Peninsula Regional delivers comprehensive medical care in town. Seniors also have access to more structured support through Peregrine Senior Living at Salisbury and John B. Parsons Assisted Living Community. The Salisbury Zoo and the riverwalk along the Wicomico add free, easy outings close to home.
Oakland
Located in far western Maryland near the West Virginia border, Oakland is a quiet town of just under 2,000 residents. The town is especially appealing to retirees who value natural scenery, a slower pace, and friendly neighbors, set in the highlands of Garrett County near Deep Creek Lake. Seniors can also take part in programs at the Oakland Community Center, which hosts fitness classes, craft workshops, and social events designed with older adults in mind.
Nature lovers will enjoy Swallow Falls State Park and Herrington Manor State Park, both located nearby and featuring trails, waterfalls, and lakes. The town also has a few local spots, such as Englanders Antiques Grill and Soda Fountain, where residents often gather. Garrett Transit Service offers transportation for seniors on a demand-response basis, and healthcare needs are met by Garrett Regional Medical Center, which is affiliated with West Virginia University Medicine.
Finishing Thoughts
Maryland is well-known for the diversity of its towns, which range across coast and mountain, summit and valley. Retiring to any of these nine peaceful towns in Maryland may make your senior years happier and more relaxed. Whether you choose a town like Hyattsville that is close to a major, bustling city, or one more far-removed like Port Deposit, which sits along a quiet, beautiful river, you can't go wrong in checking out these small Maryland towns recommended for senior living.
