8 Best Small Towns To Retire In Maryland
Seniors considering retirement in Maryland have no shortage of appealing options. Those drawn to waterfront living might choose Cambridge, with its setting on the Choptank River and its walkable historic downtown. Chesapeake City also appeals to retirees who want water views, thanks to its location on the Chesapeake and Delaware Canal and its small-town historic charm. Retirees who prefer mountain scenery may look to Oakland, a western Maryland town known for its high-elevation setting and easy access to outdoor recreation. Below are 8 options that have something for everyone.
Salisbury
The Wicomico County town of Salisbury on the Wicomico River is known as the "Crossroads of Delmarva" because of its central position on the Delmarva Peninsula. While this was vital to the town's significance years ago, as a commercial, transportation, and cultural hub, Salisbury is still an important community with an ideal location just 30 miles from Ocean City and 115 miles from Baltimore. About 17% of Salisbury's population is over the age of 60. In addition to its recreational attractions and opportunities, easy access to beaches is one of the main reasons Marylanders are retiring to Salisbury.
Being home to Salisbury University, Salisbury has a college-town atmosphere. Many retirees enjoy visiting the university's many art galleries, and may be eligible for a senior tuition waiver to take up to three courses each semester at a reduced cost, or even for free. Seniors can spend time outdoors at Salisbury City Park, taking advantage of its walking trails and listening to music at its outdoor bandstand in the summer months. Open every day except Thanksgiving and Christmas, the Salisbury Zoo appeals to all ages. Home to over 100 animals, the zoo features accessible paths and offers free wheelchairs to visitors requiring assistance while in the zoo.
Cambridge
Marylanders who are seeking a quiet, waterfront life in their retirement may want to consider the Dorchester County town of Cambridge, on the Choptank River. Within this town that is 90 miles from both Baltimore and Washington, DC, 28% of Cambridge's population is over the age of 60, meaning that those who retire here will be among many of their peers. Long Wharf Park, along the river, entices seniors with opportunities for fishing and swimming, as well as spectacular waterfront views.
Seniors may enjoy taking the Downtown Cambridge Walking Tour, which runs for 1.6 miles roundtrip and takes about an hour and a half to complete. This narrated walk takes visitors through historic sites such as Dorchester County Court House and Christ Church and Cemetery. Retirees who want to learn even more history about Cambridge should check out the Harriet Tubman Museum and Education Center, also in the downtown area. This museum celebrates the life and work of one of history's most important women, and one of Dorchester County's own. Seniors who appreciate the arts will love that Cambridge is also known as an arts mecca, with the Dorchester Center for the Arts providing classes, exhibits and education on the arts.
Havre de Grace
Sitting along the Susquehanna River where it meets the Chesapeake Bay, the town of Havre de Grace, in Harford County, is just 35 miles from Baltimore. Many retirees have been drawn to Havre de Grace, which is verified by the fact that 30% of its residents are over 60. The town features a walkable historic district, waterfront charm, and an active, tight-knit community that appeals to retirees looking for a vibrant lifestyle.
The Concord Point Lighthouse is one of Havre de Grace's most iconic landmarks, recognized by residents and visitors alike. Retirees who visit this second-oldest lighthouse in Maryland and are mobile enough may choose to climb to its top, from which views of the river and the bay are breathtaking. Seniors can also get exercise on the Havre de Grace Promenade, a 3/4-mile boardwalk running along the Susquehanna River. In addition to walking, visitors to the promenade enjoy watching the many waterfowl and learning about the Chesapeake Bay through educational signs along the way. The promenade is adjacent to Millard Tydings Memorial Park, a waterfront park with a picnic area, where many town events, such as free summer concerts in the park, are held throughout the year.
Chesapeake City
Retirees who want to live in the only Maryland town situated on a working commercial canal should choose Chesapeake City, where 20% of residents are over 60. The town sits on the Chesapeake and Delaware Canal, just 10 miles from Middletown, Delaware, and five miles from the county seat of Elkton. Chesapeake City has much more than the canal to draw retirees, however. The signature Chesapeake City bridge, built in 1948, spans 3,955 feet above the canal and is a symbol of the rise of this small town in the southern part of Cecil County.
Active retirees may opt to take the Ben Cardin C&D Canal Trail. This trail runs for 17 miles along the canal from Chesapeake City to Delaware City, Delaware, connecting with the Mike Castle Trail in Delaware. Those who prefer to learn more about the town's Ukrainian roots and history can visit the Chesapeake City Museum, a collection of artifacts and documents detailing the town's heritage. Chesapeake City's Pell Gardens, a waterfront park in the downtown area, hosts events such as free summer concerts and is a popular gathering place for residents of all ages.
Chestertown
Chestertown, on the Chester River in Kent County, is about 45 minutes from Smyrna, Delaware and an hour and a half from the state capital of Annapolis. It is clear that Chestertown is a great small Maryland town to which to retire, as 30% of its population is over age 60. Chestertown, home to the liberal arts school Washington College, is another town with the college-town vibe. Retirees who want to keep feeling young may enjoy attending on-campus events such as jazz recitals, poetry readings, and choral concerts.
Attending the Chestertown Farmers Market, held every Saturday morning downtown, is a favorite pastime of many senior residents. Vendors here sell fresh, local produce year-round. The Wayne Gilchrest Trail is perfect for active retirees, running 2.1 miles from Wilmer Park to Gateway park. This asphalt trail is ideal for walkers, bikers, and is also wheelchair-accessible. Chestertown's signature events along the water include the Chestertown Tea Party Festival held each Memorial Day weekend. This event blends history with the chance to socialize with friends, neighbors, and the many visitors who attend.
Oakland
Seniors who prefer the mountains to the eastern shore will delight in the Garrett County town of Oakland in far western Maryland, near the West Virginia border. Sitting 2,500 feet high in Appalachian Mountains, Oakland is 55 miles from Morgantown, West Virginia and 120 miles from Pittsburgh, Pennsylvania. A whopping 39% of its residents are over the age of 60, highlighting Oakland's excellence as a small retirement town.
Oakland has an accessible downtown area featuring the Ruth Enlow Library of Garrett County, within walking distance from downtown shops and businesses. Retirees and residents of all ages are often found browsing its stacks of books or using its computers. The Garrett County Historical Museum, also downtown, is ideal for history-loving seniors. This museum provides a look into the town and the county's history, recounting a time when trains ran through Oakland 12 times each day. Glades Park offers recreational opportunities including a fishing pond and a paved, wheelchair-accessible walking trail ideal for retirees. This trail connects to the main town walking trail which covers almost three miles of Oakland.
Hagerstown
Called the "Hub City" for its central location, Hagerstown, in Washington County, is just 75 miles from Baltimore and 70 miles from Washington, DC. In addition to its easy access to major cities, retirees move to Hagerstown because of its small-town lifestyle and abundance of amenities. Its popularity among the senior set is evident, as 20% of Hagerstown's residents are over 60.
Hagerstown City Park, celebrating its 100th year, is filled with trails, a lake, and a picnic area, and is frequented by residents of all ages. The park also houses the Washington County Museum of Fine Arts, appealing to arts-loving seniors. This museum features older pieces as well as showings of the works of new artists in the area. The Jonathan Hager House Museum, another town landmark, is the refurbished home of the founder of Hagerstown, built in 1739. Seniors, and others, may enjoy guided tours of this historic home, built over a spring that has never failed, in the downtown city park area of town.
Hampstead
Retirees who prefer proximity to Baltimore yet still want to live in a small town might choose the town of Hampstead, in Carroll County. Just 30 miles from Baltimore, a quarter of Hampstead's population is over the age of 60, stressing the appeal that this town has for retirees. The advantages of being near city amenities yet living in a more relaxed, smaller community that has its own amenities draw many retirees to move to Hampstead.
Chief Sites Memorial Park in Hampstead is popular among senior residents for its paved and gravel walking paths, picnic areas, and picnic tables that are wheelchair-accessible. To learn more about the history of Hampstead, retirees may visit the Hampstead Train Station. Created on the site of an old railroad depot, this museum explains the importance of the location, created in 1912, on the Western Maryland Railway Line, transporting goods to and from Baltimore. The train station area is also home to an outdoor amphitheater, which hosts Music in the Park at Hampstead Memorial Park. Seniors and others enjoy the variety of music offered in this free summer program.
Migrate to These Maryland Towns in Retirement
Whether you are searching for walkable downtowns, historic charm, or vibrant local culture, these eight Maryland towns provide amenities for retirees of all ages. From the far western mountains of Oakland to the eastern shores of Cambridge, seniors can choose the perfect setting for the lifestyle they seek. They can enjoy meeting up with their peers at farmers markets like the Chestertown Farmers Market or events such as Hampstead's Music in the Park. With plenty of opportunities to remain active, these Maryland communities enable retirees to stay connected and engaged.
