7 Most Hospitable Retirement Towns In Maryland
Retirees seeking a four-season state to enjoy their golden years can discover a fulfilling lifestyle in Maryland. Often referred to as “America in Miniature,” Maryland's diverse landscape ranges from the rolling hills of the Appalachians to the shores of Chesapeake Bay. Its varied counties are filled with warm and welcoming towns and colorful communities where retirees can settle in quite comfortably. Beautiful parkland, outdoor activities, exciting community volunteer opportunities, active event calendars, and exposure to the arts help create a rich and enjoyable life.
Here are the seven most hospitable retirement towns in Maryland that retirees would be proud to call home.
Easton
With its tree-lined streets, charming red brick buildings, and cobblestone sidewalks, Easton is truly one of Maryland's best small towns for retirement. Bump into neighbors shopping for fresh produce and locally made goods at two farmers' markets in town. The indoor Amish Country Farmers Market is open Thursday through Saturday, so there is no need to fight the weekend crowds, though the weekly market on Saturday mornings is always a treat. For leisure, you can head to Hog Neck Golf Course, where you can hone your skills at the putting green, practice your swing at the driving range, or meet up with neighbors for a friendly round on the 9- or 18-hole championship courses.
Easton also holds several festivals and events throughout the year to bring the community together. Kick off the holiday season at the Festival of Trees on Thanksgiving weekend, followed by the Olde Tyme Holiday Parade the first weekend of December. The Academy Art Museum is a gathering place for art lovers with weekend workshops to discover your hidden talent and meet like-minded creatives in the community. Visiting lecturers share their perspective on art, and events range from yoga to classical music concerts in the galleries.
Chestertown
Chestertown is another Eastern Shore gem where Maritime heritage meets college town pride. Sitting on the banks of the Chester River, Chestertown is rich in history, dating back to 1706. The brick-lined streets are dotted with 18th-century homes, and the downtown offers a mix of eateries, cafés, shops, and galleries. As a cap and gown town, you can follow Washington College’s event calendar to find exciting concerts, guest lectures, and workshops to attend. This college town helps keep you vital and young with community events that encourage you to learn new things.
A band of community volunteers joins forces to celebrate the town's rich maritime heritage at several annual Chestertown events. The Chester River comes alive during the annual Sultana’s Downrigging Tall Ship & Wooden Boat Festival when ships cruise en masse with their sails unfurled. The Chestertown Farmers & Artisans Market has been a community gathering place for over forty years. Open from 8 to 12 every Saturday, you can discover local makers of gourmet and specialty items, sample the goods, and stock up on all your staples from meat and cheese to bread and produce. Locals also rub elbows and enjoy casual conversation at downtown eateries like Bad Alfred’s. The transformed historic garage and filling station is a welcoming space bringing people together over food and site-crafted spirits.
Hancock
Retirees who live an active, outdoorsy lifestyle will find Hancock’s location between the Potomac River and the Appalachian Mountains to be a perfect town to hang their hats. Hancock is Maryland’s only official Trail Town, with access to miles of pathways and convenient out-and-back loops through hundreds of acres of parkland. Join the Washington County Bird Club to meet fellow birders, take advantage of the local trails, and participate in field trips. Fort Frederick State Park and the C&O (Chesapeake & Ohio) Canal Towpath are popular areas to observe species in their natural habitat. Cyclists and hikers also have access to the park’s 585 acres along both the towpath and Western Maryland Rail Trail.
Volunteering combines your love of hiking and nature with the opportunity to discover fun facts about your new home. Certified Volunteer Rangers help maintain Fort Frederick’s natural and cultural resources while participating in a wide range of exciting programs, duties, and events, and Volunteer Roving Interpreters hike the canal towpath, greeting visitors and sharing information about the trail, from history to geology and ecology to fun facts. Even shopping in Hancock is an adventure with eclectic destinations like the Blue Goose Market offering fresh produce, gourmet food items, and mouthwatering baked goods.
Thurmont
Thurmont’s idyllic location in northern Maryland near Catoctin Mountain Park and Cunningham Falls State Park makes it a popular gateway to the mountains. If you are planning to downsize but do not want to give up your garden, the Thurmont Community Garden provides locals without private yards a designated plot within walking distance of their homes. The gardens are the work of Thurmont Green Team volunteers who are always looking for new members to help maintain the town’s Sustainable Maryland Community certification. You can also put your green thumb to work helping with Main Street Beautification initiatives or participating in local events.
The community is very social, gathering in the quaint historic downtown to celebrate festivals throughout the year. During the Art & Wine Stroll, Main Street is transformed into an open-air gallery where artists and artisans display their work and local wineries, breweries, and distilleries serve up drinks alongside a convoy of food trucks. A free membership at the Thurmont Senior Center comes with lots of perks and community connections. Enjoy a hot lunch with fellow members, get physical at exercise classes, or learn about a wide range of volunteer opportunities.
Annapolis
Annapolis is located at the mouth of the Severn River on Chesapeake Bay. Retirees with loved ones in Baltimore and Washington, D.C. can live a vibrant lifestyle in this bougie small town just a short drive from friends and family. Red cobblestone sidewalks and streets in downtown Annapolis add historic character to a town that is a little more cosmopolitan than your average retirement community. The Main Street from Church Circle to City Dock is a hub for year-round festivals, including “the world’s largest crab feast” every summer.
Boaters cruise the Severn River out to Chesapeake Bay or follow the narrow waterway along Ego Alley. You can also spend lazy days casting your line with fellow anglers on Chesapeake Bay along over 500 miles of scenic shoreline. The historic town inspires retirees to find new interests and make new friends, including volunteering at Historic London Town & Gardens. Get involved in a wide range of activities with like-minded locals, from gardening to engaging visitors as a docent. Meanwhile, Maryland Hall is the heart of the community’s cultural and arts experiences, where everyone is welcome to participate in workshops, view exhibitions, and explore their creative side. Try your hand at painting, take up knitting or embroidery, or explore the world of printmaking.
Chevy Chase
Chevy Chase is a charming town located in central Maryland’s Montgomery County. Woodend Nature Sanctuary offers accessible trails through 40 acres of forests and meadows where pond habitats and a trickling stream offer hours of exploration and discovery. Join fellow nature lovers on sanctuary field trips, take classes, or sign up for an adventure with Nature Forward, exploring wildlife and nature beyond Maryland and the mid-Atlantic region. You can also take advantage of the cherry blossom season with fellow townees away from the crowds of Washington. Stroll the Kenwood neighborhood to see this town in all its glory during the three-to-four-day window when the trees are in full bloom.
Socialize and learn new things at Chevy Chase Library, like the Handcrafters Meetup, where crafty locals come together to share their latest projects, exchange ideas, and get tips from volunteer crafters. You can also join fellow bookworms at the Town of Chevy Chase Book Club to keep up on the latest recommended reads. The club also holds author talks and happy hour events, where guest authors read from new releases, answer questions, sign books, and mingle with members at the wine and cheese party. Meanwhile, Ch/Art joins the D.C. and Maryland Chevy Chase communities through cultural events. Show off your best casserole at a potluck social, sit in on lectures, take some classes, and support the art community by volunteering your time.
Frostburg
Set against the stunning backdrop of the Appalachian highlands, Frostburg’s historic downtown and quiet neighborhoods offer a picturesque retirement town. Mountain City Traditional Arts is located in downtown Frostburg's Arts & Entertainment District. The center focuses on Appalachian-based, handcrafted folk art and hosts classes and workshops that emphasize traditional art forms. A small venue also presents occasional live music performances and presentations. Volunteering for the Cultural Events Series at Frostburg State University is another opportunity to get involved in the community. Lovers of the arts and theater provide services during performances as ushers and ticket takers while enjoying the show themselves during their shift.
Meanwhile, new experiences await at Frostburg Public Library, where retirees can join the book club or attend lectures and events. Get to know your neighbors at the weekly social hour for hot drinks, conversation, and games. Wandering Frostburg’s historic downtown is also an activity unto itself, where many businesses have been serving the community for generations. Princess Restaurant’s diner-style fare has been satisfying locals for 80 years, where tabletop jukeboxes and booths serve a side of nostalgia with every home-cooked meal.
Whether your retirement plans are about staying active, pursuing new interests, or contributing to your community, Maryland is full of possibilities. From seaside sweet spots on Chesapeake Bay to quiet communities nestled in the mountains and vibrant neighborhoods enriched through the arts, these seven most hospitable towns in Maryland allow you to ease into retirement at your own pace.
