9 Best Maryland Towns For Retirees

Retirees love Maryland. Maryland is centrally located in the Mid-Atlantic region of the US and is surrounded by large metropolitan areas in Delaware, New Jersey, Pennsylvania, and Virginia. Retirees needing or wanting to visit cities like Washington, D.C., find themselves a short drive away. The problem with retiring in major cities is the cost. Choose Maryland and get the best from living in a smaller town or rural area surrounded by nature, while still being close to big city amenities. Here are the nine best Maryland towns for retirees.

Easton

Easton is the perfect retirement location for those looking to enjoy the small-town atmosphere that’s also close to several major cities. From Easton, residents can access Wilmington, Baltimore, Annapolis, and Washington, DC. Easton sits not far from Chesapeake Bay, which provides open waters for sailing, canoeing, and kayaking. Many residents also take advantage of crabbing along the Easton shorelines.

Retirees can walk or relax at the Talbot Historical Society Museum and Garden year-round and learn about the local history while also savoring the beauty of a groomed New England garden. Retirees can shop weekly at the Amish Country Farmer’s Market and the Easton Farmer’s Market. Get fresh, local produce, seafood, baked goods, dairy, and meat, as well as furniture and handcrafted goods.

Retirees who appreciate nature frequent the Pickering Creek Audubon Center. The center protects 400 acres of forests, wetlands, and the wildlife living within it. Learn from ongoing lectures, field trips, or hikes to experience the beauty of the area. Golfers will be in heaven at the Hog Neck Golf Course. The course is an 18-hole championship course with a pro shop and driving range. Seniors build community at Brooklett’s Place - Talbot County Senior Center. Find services, education, and recreation all in one location. For those looking for senior living communities, check out Bayleigh Chase and Londonderry on the Tred Avon.

Chestertown

Chestertown is a waterfront town located on the Chester River. Chestertown is small but offers retirees a variety of outdoor activities and cultural events within a friendly and open community. For retirees looking to settle down in a quiet town that moves at a slower pace, Chestertown is perfect. Housing in Chestertown is more affordable than most cities in Maryland. Of course, if retirees want to live in Historic Downtown Chestertown, the price is higher compared to homes on the outskirts of town.

Art lovers flock to the Garfield Center for the Arts. The center is within a historic theater that still hosts live performances, including plays, concerts, and special community events. Retirees keep up with the latest performing arts right in their own backyard. Residents and visitors alike take part in tastings at the Chester River Wine & Cheese Co. Sample artisanal cheeses, locally crafted wines, and charcuterie boards for every taste. Seniors looking for outdoor activities go to several local parks like Wilmer Park and Fountain Park. Both parks offer extensive manicured lawn areas, views of the Chester River, and walking paths.

For those looking for more wild surroundings, take a short drive and bird watch, hike, or bike at the Eastern Neck National Wildlife Refuge. Chestertown does offer seniors a place to convene at the Chestertown Senior Center. Senior housing options include Heron Point of Chestertown for independent retirement living.

Adamstown

Adamstown is a suburb of the city of Frederick and offers retirees the option of living in the country while enjoying the amenities of city life. Live in the peace and quiet of nature and be less than a 30-minute drive from Frederick. Retirees choosing Adamstown benefit from living away from the city without being so far away that they feel isolated and alone. Residents of Adamstown may not have as many amenities in town, but they have a strong community. Residents relish annual events like the Carroll Manor Fire Company Annual Carnival.

Retirees looking for challenging hikes head to nearby Sugarloaf Mountain and explore the Northern Peak Trails. For easier trails, try the C&O Canal trails for hiking and biking. Golfers head down to the Worthington Manor Golf Club. The club is a short drive from Adamstown to Frederick. The club offers a top course that’s one of the best in the mid-Atlantic area.

Seniors have access to one of the larger retirement communities at Buckingham’s Choice Senior Retirement Community. There’s no local senior center in Adamstown, but there are two in Frederick: The Frederick Senior Center and the Urbana Senior Center.

Westminster

Westminster is another small town that provides retirees with local activities while still living near the amenities of large cities like Baltimore and Washington, DC. Living in Westminster is significantly more affordable since it’s outside the city. Located in Northern Maryland, Westminster supplies retirees with an inexpensive and welcoming community.

The town provides access to several natural areas for retirees looking to get out in nature. Visit the Bear Branch Nature Center for hiking and biking trails that support active bird and wildlife watching. Westminster also supports several town parks where visitors can picnic, walk, or enjoy the open grass fields. Retirees stay in touch with the arts at the Carroll County Arts Center. Visit the center for a variety of changing exhibits as well as stage performances and concerts.

Westminster retirees appreciate local access to Piney Run Lake for water activities, including fishing and kayaking. Seniors find community, educational opportunities, and recreation locally at the Westminster Senior & Community Center. Benefit from the services offered by the center to support healthy aging in Westminster. For seniors looking to live in a retirement community, check out Brightview Westminster Ridge, Country Meadows, or the Westminster Terraces.

Cambridge

Seniors looking to retire in an affordable waterfront community have found a match in Cambridge. Relish a quiet, easy-going retirement near Chesapeake Bay with access to the Choptank River. Cambridge is a maritime harbor town with water and nature views that will last a lifetime. Downtown Cambridge serves as a central gathering place with local shops, cafes, and art galleries like the Main Street Gallery or The Hive: Art & Goods.

Retirees in Cambridge benefit from a lower cost of living, too, which is surprising for such a beautiful waterfront community. Check out the Hyatt Regency Chesapeake Bay Resort in town that delivers access to a golf course, spa, and marina. Seniors looking for hiking and biking in nature utilize the entire walkable town, including its piers and parks. For more natural trail options, check out the Blackwater National Wildlife Refuge. Discover local history at the Brannock Richardson Maritime Museum. Don’t miss the Harriet Tubman Museum & Educational Center, which honors the famed abolitionist.

Discover the senior community at the local Cambridge Mack Senior Center or the Delmarva Community Services Center at Chesapeake Grove. Find several senior living communities, including the Bradford House and Conifer Village at Cambridge.

Sykesville

Sykesville is a suburb of Baltimore and won Budget Travel’s “Coolest Small Towns in America” award in 2016. Sykesville supplies Civil War history buffs with more than a few museums and locations of interest. Retirees can also spend time visiting the Gate House Museum. Retirees can get outdoors and utilize Piney Run Park, the Sykesville Linear Trail, or find more challenging options at the nearby Patapsco State Park. Patapsco State Park takes visitors through the Patapsco River Valley. Camp, fish, hike, bike, or ride horseback and delight in the peace and quiet of nature.

Seniors enjoy Sykesville’s small-town charm and lower cost of living. Plus, they still live only 30 minutes from Baltimore. Seniors who love the city can benefit from living in Sykesville while still being close to amenities and activities in busy Baltimore. Skyesville furnishes seniors with local senior services, recreational, and social activity options at the South Carroll Senior & Community Center. Retirees looking for senior living communities should consider Winifred Manor and the Village House.

Salisbury

Salisbury is a tranquil town sitting on the Wicomico River with surprisingly affordable waterfront living options for retirees. Housing and general living costs run lower than the national average in Salisbury. Salisbury supplies residents with an active Downtown Arts and Entertainment District thanks to the influence of Salisbury University. The influx of youth, families, and seniors creates a growing business district with local shops, restaurants, and festivals.

For retirees wanting to get outdoors, there are a wide variety of options for biking, hiking, and boating. Find trails within the Pemberton Historical Park, Salisbury City Park, or Schumaker Pond. Don’t forget to try walking the paths around the Salisbury Zoological Park. Discover senior services and community activities locally at the Mac Inc Area Agency on Aging. For senior community housing options, consider Peregrine Senior Living or Commonwealth Senior Living.

Hagerstown

Retirees looking to settle down near, but not in, a large metropolitan area will love Hagerstown. Hagerstown is the perfect retirement destination for active seniors who love the outdoors. Hagerstown is an affordable small town near both Baltimore and Washington, DC, in Western Maryland. Hagerstown is the seat of Washington County and thus a hub for both county government and business.

Hagerstown furnishes retirees with access to a vibrant, thriving community that includes easy access to nature. Hike or bike the Greenbrier State Park trails or visit several city parks like Hagerstown City Park, Fairgrounds Park, or Pangborn Park. Retirees can locate and explore over 21 historic stone arch bridges in the county. Seniors connect at the local Washington County Senior Activities Center. Find social connections and access a variety of services or meet up for special events or exercise classes. Seniors looking for retirement community options need to check out VIVA Senior Living at Hagerstown or Emerald Pointe.

Cumberland

Cumberland is for retirees looking for affordable small-town mountain living. The town sits near the Potomac River and features views of the surrounding Allegheny Mountains. Bikers and hikers have accessible trails with local access to both the Chesapeake & Ohio Canal path and the Great Allegany Passage that runs northwest from Cumberland all the way to Pittsburgh. Cumberland offers retirees a lower cost of living. The value of living in Cumberland doesn’t mean retirees are settling for a lower quality lifestyle.

The mountain town allows residents access to numerous trails and parks. Bikers can cycle from the Cumberland Narrows, across the Mason-Dixon Line, and then pedal all the way through Pennsylvania's Laurel Highlands to Pittsburgh’s Point State Park. The trails are accessible from various points and provide nearly endless opportunities to experience nature in all its scenic wonders. Train enthusiasts can ride the Western Maryland Scenic Railroad and experience the wonders of the Allegheny Mountains on a historic restored steam engine.

In town, experience the arts and entertainment district in downtown Cumberland. Visit the Saville Gallery, the Schwab Mountain Maryland Gallery, and the Cumberland Theatre. Eat in historic downtown at a variety of restaurants like City Lights, or, for fine Italian food, try Ristorante Ottaviani. Seniors can savor the historic downtown and find community at the Cumberland Senior Center. Find resources for seniors, recreation, and social events. Seniors looking for retirement communities should check into Cumberland Meadows Senior Living.

Maryland provides retirees with several options for experiencing an affordable and quality lifestyle. The state has local access to outdoor recreation for any active senior. Most small towns include a local senior center as well as multiple types of senior housing options. Maryland’s popularity is boosted by its reputation as a moderately tax-friendly state. For example, seniors earning less than $50,000 a year may qualify for several tax relief measures. Nature, small town living, and economic benefits make Maryland’s towns attractive to retirees.