10 Best Small Towns in Maryland to Retire for 2026
If you’re looking for a peaceful, charming place to enjoy your retirement, Maryland’s small towns offer the perfect mix of coastal beauty, access to healthcare, rich history, and tight-knit communities. Whether you want water views, proximity to the arts, or access to a high-quality continuing care retirement community (CCRC) like those offered by Acts Retirement-Life Communities, here are 2026’s 10 best small towns in Maryland to retire.
Easton
Easton, home to Acts’ Bayleigh Chase, is often named one of the best small towns in America for good reason. This town on the Eastern Shore offers a thriving cultural scene, with the Avalon Theatre, art galleries, and frequent festivals. It’s also home to top-notch medical care through University of Maryland Shore Medical Center. Easton blends historic charm with modern amenities, offering retirees a vibrant yet peaceful lifestyle in close proximity to Chesapeake Bay.
Chestertown
Nestled on the Chester River, Chestertown is a historic waterfront town that combines colonial charm with a strong sense of community. Its walkable downtown, lined with 18th-century architecture and cozy shops, hosts frequent cultural events and a beloved farmers market. Healthcare access is provided by the University of Maryland Shore Medical Center at Chestertown. Chestertown is also home to Heron Point, an Acts community that offers an incredible lifestyle for older adults and stunning views.
Lanham
Lanham offers a quieter suburban setting while maintaining easy access to Washington, D.C. and Baltimore. Residents of the area benefit from a diverse community, proximity to cultural institutions, and high-quality healthcare. Fairhaven, an Acts community located in the area, offers beautiful campus living with well-appointed residences, a full continuum of independent living and health services, and vibrant lifestyle options.
Sykesville
Located in Carroll County, Sykesville is a picturesque small town with historic buildings, boutique shops, and a charming Main Street that makes it ideal for retirees seeking peace with character. It also offers convenient access to parks, trails, and medical facilities. Residents here enjoy a relaxed lifestyle with small-town hospitality. Nearby, you’ll find Fairhaven, another Acts community known for its welcoming environment and engaging programs.
Annapolis
Maryland’s capital city may surprise some as a “small town,” but with its close-knit feel, walkable downtown, and waterfront setting, Annapolis certainly fits the bill as a great small town in Maryland for retirees. Its rich naval history, vibrant arts scene, and proximity to the Chesapeake Bay make it ideal for active retirees. Acts’ Buckingham’s Choice, located in nearby Adamstown in Frederick County, serves retirees from the Annapolis region with an active lifestyle and upscale amenities.
St. Michaels
St. Michaels is a postcard-perfect harbor town that offers a serene retirement experience. Known for its maritime history and quiet charm, it draws retirees who appreciate fine dining, sailing, and tranquil waterside views. Though there’s no Acts community in St. Michaels itself, its close proximity to Easton makes Bayleigh Chase a convenient option for those who want to live nearby while enjoying top-tier senior services.
Cambridge
Cambridge is another gem on Maryland’s Eastern Shore, offering retirees a welcoming community, affordable housing, and deep cultural roots. The historic district, waterfront parks, and close proximity to Easton’s Bayleigh Chase make this a smart choice for those seeking a balance between affordability and access to care.
La Plata
Located in Southern Maryland, La Plata features a strong sense of community, great local dining, and proximity to the greater Washington metropolitan area. With access to quality healthcare through the University of Maryland Charles Regional Medical Center, La Plata is ideal for seniors looking for a convenient blend of suburban and rural living.
Bel Air
Bel Air, located in Harford County, offers a slower pace of life, tree-lined streets, and a host of cultural and recreational activities. With medical facilities, art galleries, and nature trails all within reach, Bel Air is a relaxing and scenic place for retirees who want to stay active.
Rock Hall
For retirees who love the water, Rock Hall is a quiet fishing village on the Chesapeake Bay that offers beautiful sunsets, fresh seafood, and a friendly community. While smaller than other towns on this list, its peaceful atmosphere and proximity to Chestertown make it ideal for those looking for a quiet, contemplative retirement experience.
Why Maryland Small Towns Appeal to Retirees
Start with the luscious scenery. Then consider the nearby healthcare infrastructure, rich cultural and recreational amenities, and tax advantages for retirees. The state provides a pension exclusion of up to $34,300 (as of 2024), helping to lower overall retirement costs. With beautiful coastal landscapes, vibrant communities, and easy access to senior-focused resources, these towns create the perfect retirement environment.
Learn More About Retiring in Maryland
From the artistic flair of Easton and Chestertown to the calm waters of Rock Hall and the urban-suburban blend of Lanham, Maryland’s small towns cater to a variety of retirement dreams. With several communities operated by Acts Retirement-Life Communities across the state, Maryland is more than just a beautiful place to retire—it’s a home where seniors can thrive with confidence and care.
Looking to explore these retirement options? Learn more about Acts' Maryland communities and schedule a visit today.
