6 Friendly Towns To Retire In Maryland
Its history and geographic location as the center of the Eastern Seaboard distinguish Maryland as a destination. From the Appalachian Mountains to Chesapeake Bay, Maryland’s diverse landscapes and climates make it a fascinating place to visit. Maryland is where the Mason-Dixon Line lies on its northern border with Pennsylvania. Its position as the northernmost Southern state is part of Maryland's image, while the importance of the Chesapeake Bay cannot be overstated. Maryland’s critical location drives the state's culture and economy. For retirees seeking ambiance, friendliness, and a high quality of life, Maryland’s small cities and towns are worth considering.
Easton
A courthouse was built in 1710, and from that point, the city of Easton began to grow. Before this, a meeting house for the Society of Friends was built between 1682 and 1684, while Welsh Puritans settled the Wyle plantation in the 1650s. That land is still owned by the family today, 11 generations later. With a population of 17,342, Easton is a small city that boasts the charms of a small town, yet offers access to larger cities such as Baltimore and Washington. It also has a reputation for outstanding medical services. Located by Chesapeake Bay and its tributaries, maritime culture is a crucial part of Easton’s past and present. Outdoor water activities abound, including sailing, kayaking, fishing, and especially crabbing. The Easton Town Center is a historic district with Colonial and Victorian architecture. The Town Center offers shopping and dining options for every budget, along with antique shops and galleries. For golfers, there are several courses in the area.
The Eastern Shore is ideal for bird watching, especially for migratory birds who make the area a crucial rest stop. For culture, there’s the Chesapeake Chamber Music Festival, a two-week event taking place every June in venues throughout the town. Easton also hosts the Annual Plein Air Competition & Arts Festival, celebrating the technique of painting outdoors that inspired the Impressionists in the 19th century. To soak up more history, the Talbot Historical Society Museums & Gardens is a Federal-style garden with a research center and two historical houses in the Georgian and Federal styles, featuring exhibits.
Berlin
On the eastern shore, a town of 4,485 sits, steeped in history and culture, offering the small-town atmosphere you may be seeking. For the retiree looking for a coastal town to relocate to, Berlin is a thriving and diverse community that has much to offer. First settled by Europeans in 1677, Berlin was incorporated as a town in 1868. The Berlin Commercial District is also its historical district, featuring over 47 buildings from the 19th century. Many of the buildings are constructed as rows with common walls, giving the district its unique and cohesive look. Much of Berlin’s character and town life centers on its downtown area, where historic buildings now house boutiques, cafes, restaurants, and seafood markets featuring local fare. The Berlin Commercial District Welcome Center, located at 14 S. Main Street, features a kiosk open 24 hours a day, seven days a week.
Berlin is a walkable town, and the beauty of its historical neighborhoods and the streets lined with old-growth trees is well worth a stroll. Berlin is also known for its artistic and cultural activities, with artisans, artists’ studios, and galleries throughout the downtown. Heron Park, a repurposed site that was formerly a chicken processing plant, now features ponds and a woodland area, attracting migratory birds that can be viewed up close. Off the coast of Berlin lies Assateague Island and the Assateague Island National Seashore, a nature preserve. It is a crucial resting and feeding space for migratory shorebirds and other bird species, with over 320 species of birds found at different times of the year.
Chestertown
Chestertown is a town of 5,532 that is rich in Colonial, Revolutionary, and maritime history. Founded in 1706, Chestertown was designated a Royal Port of Entry, and the ensuing shipping boom helped establish the town as a commercial hub. In the 18th century, Chestertown was second only to Annapolis as Maryland’s leading port. In 1774, residents of Chestertown staged the Chestertown Tea Party on the Chester River, inspired by Boston’s example. The annual Chestertown Tea Party Festival takes place every Memorial Day Weekend to commemorate the historic event. Chestertown’s history is a key part of its charm, with tree-lined streets filled with Colonial architecture. Its vibrant downtown commercial district offers a wide range of shopping, restaurants, galleries, and cafes suitable for any budget, making Chestertown an ideal place for retirees looking to resettle in a town rich in history and friendly residents.
The Port of Chestertown Marina is situated on the riverfront, offering numerous opportunities for boating and fishing. The riverfront promenade is ideal for cycling, while offering opportunities for fishing at the pier, kayaking along the river, or visiting Wilmer Park. In the downtown commercial district, High Street is closed to cars in the summer, providing a pedestrian walkway and al fresco dining from the many restaurants. Locally caught seafood is featured on many menus, including The Kitchen at The Imperial, situated in a historic three-story luxury hotel. Chestertown boasts a vibrant arts scene, and the Garfield Center for the Arts, located at the Prince Theatre, a historic landmark cinema from the silent era, presents live performances.
Saint Michaels
The key to Saint Michaels charm is its laid-back coastal feel. The town of 1,094, situated on the Chesapeake Bay, boasts a rich maritime history that is a significant part of its appeal. The area was first settled by Europeans in the 17th century, establishing a shipbuilding industry and cultivating tobacco. St. Michaels played a key role in the War of 1812, when, in 1813, British Admiral George Cockburn targeted the town for its shipyards, and a militia battery was established as a defense. This sense of history is prevalent in the city, and its quiet, small-town ambience should appeal to retirees seeking a friendly and historically vibrant coastal town. The commercial district is centered around Talbot Street, which features numerous boutiques, galleries, and restaurants. The street is lined with preserved Colonial buildings, helping to create a time-traveling feel.
In the warmer months, the St. Michaels Farmers Market features local produce and other fare. Whether you go to the market, to the seashore, or visit the local restaurants, between April and November is crab season. The area’s seafaring history is the focus of the Chesapeake Bay Maritime Museum. The museum is situated on an 18-acre waterfront area that includes Navy Point, formerly a cluster of seafood processing facilities. The museum also hosts the annual OysterFest every October, with food, live music, and other activities. A recreated crab shack, Waterman's Wharf, gives visitors hands-on experience harvesting seafood such as crabs, eels, and oysters.
Havre de Grace
Located at the mouth of the Susquehanna River, the area around this city of 12,952 was first settled by Europeans in 1608. A small hamlet during the Revolutionary War, it was visited by legendary war hero General Lafayette, who said the area reminded him of the seaport Le Havre in France. Naming the community Le Havre-de-Grâce, the residents incorporated the town as Havre de Grace in 1785. That romantic name suits the city well, with its well-developed waterfront and the five-acre waterfront Downtown District. The Havre de Grace Promenade is a three-quarters-of-a-mile boardwalk along the river, offering views of where the river meets Chesapeake Bay. It connects two parks, with connections along the way to the downtown, where Havre de Grace is especially known as an antiquing destination.
Local fishing and crabbing history is the focus of the Havre de Grace Maritime Museum. The museum is located within the Concord Point Heritage Corridor, in the historic district. In the Susquehanna River Valley, Susquehanna State Park offers extensive mountain biking trails and access to the river for fishing and boating. The annual Havre de Grace Waterfront Festival takes place at Concord Point Park and extends into other areas, including downtown, and features seafood, music, food trucks, beer gardens, artisans and craft, plus kid zones and a crab soup contest.
Sykesville
Sykesville is a town of 4,622 close to Baltimore, but far enough away to retain its small-town charms. First settled by Europeans in the 1800s, the main pursuit of these mostly German and Scottish immigrants was the area’s farming and mining. The land where Sykesville was built was a 3,000-acre plantation called Springfield Estate, owned by shipbuilder William Patterson. The arrival of the railroad encouraged an influx of new residents and businesses, and the town grew. The Sykesville Historic District is the town’s walkable downtown centered around Main Street. The architecture from the 19th and early 20th centuries includes a mix of styles, such as Victorian, Queen Anne, and Colonial Revival. Today, the Historic District is home to a variety of shops, restaurants, and other small businesses. Sykesville’s friendliness, culture, and history make it an inviting community for retirees.
The B&O Train Station is located in the Historic District next to the river. The Queen Anne-style station was designed by E. Francis Baldwin and built in 1883. It is currently a restaurant with seating on the original outdoor platform. The Sykesville Gate House Museum covers the history of the town in a historic house in Millard Cooper Park. The Piney Run Park Nature Center is part of Piney Run Park, offering environmental education programs. The park itself is open for hiking, boating, and fishing. The Art & Wine Festival takes place in the spring each year, while the fall Craft Beer Festival is another highlight of the town’s events calendar.
Travel Back in Time in Some of Maryland's Friendliest Towns
The towns and smaller cities of Maryland are known for their friendly spirit and sense of community. For retirees looking for small-town life, there are many choices, with all the amenities you want. The beautiful shores of Chesapeake Bay give Maryland its maritime flavor, while the towns with their historic architecture and tree-lined streets set a certain pace not often found in larger communities. For seafood, Colonial history, revitalized historic districts brimming with activity, there just may be a place for you to settle down in retirement.
