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 serene way of life. These nine smaller towns, all with populations under 50,000, are perfect for a comfortable retirement. From the riverside charm of Port Deposit to the cultural appeal of Cambridge and the mountain serenity of Oakland, each offers a unique setting ideal for peaceful and fulfilling senior living.

Crisfield

One of the most affordable towns for seniors in Maryland lies at the state's southernmost point. Median home values here are around $165,000 as of June 2025, far under the state average of $430,000. The small waterfront village, founded in 1666, is known as the "Crab Capital of the World." 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 beauty, with nearby Janes Island State Park housing a variety of wildlife, including crabs, birds, and fish.

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. Median home values here are just under the state average, at $410,000, a great reason many are retiring to Chesapeake City.

The streets of Chesapeake City are filled with historic buildings from the 19th century that, today, house quaint shops such as Chick's and The Mercantile at Back Creek. Along the waterfront, Pell Gardens is a cozy 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." They also acknowledge that median home values here are $420,000, $10,000 lower than the state average.

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, is attractive to many retirees, not only because of its median home values of $405,000. It is also a safe community, with only one violent crime in 2019, according to FBI data. Healthcare is also covered 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 34-foot-high monument that was the first one ever dedicated 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 majestic Appalachian Mountains. It lies two hours southeast of Pittsburgh, Pennsylvania. Almost a quarter of Cumberland's population is over age 65, partly due to low median home values of around $150,000. 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.

Port Deposit

Port Deposit, in Cecil County, is home to just over 600 residents, making it one of Maryland’s smallest communities. This quaint town along the Susquehanna River is the ideal serene environment for seniors longing for quiet beauty during their retirement years. Home values under the state average, at $400,000, also don't hurt. 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.

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, out of which 20% are over age 65, there is a bustling social environment for seniors. Median home prices are well below the state average, at $265,000 as of June 2025. Seniors moving to Cambridge will enjoy the friendly, walkable streets and boatable waters. 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 charm 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 vibrant 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. Even with so much to offer, the town has an affordable median home value of around $260,000, perfect for those on a budget.

Oakland

Located in far western Maryland near the West Virginia border, Oakland is a quiet town of just under 2,000 residents. Median home values are around $305,000, well below the Maryland average as of June 2025. The town is especially appealing to retirees who value natural scenery, a slower pace, and friendly neighbors. 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 charming 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, from coastal to mountain, summit to valley. Retiring to any of these nine peaceful towns in Maryland may make your senior years happier and more serene. Whether you choose a town like Hyattsville that is close to a major, bustling city, or one more far-removed like Port Deposit, which is along a quiet, beautiful river, you can't go wrong in checking out these small Maryland towns recommended for senior living.