9 Best Small Towns In Maryland For Retirees

Maryland is not a large state, containing an area of 12,407 square miles, but it is one of the most beautiful and welcoming states on the East Coast. One of the most stunning features of Maryland is the many rivers and bodies of water within its borders. From the Susquehanna River to the Chesapeake Bay, there are miles of coastline and river beds to explore and appreciate. Maryland is an ideal place for retirees who hope to experience an active outdoor lifestyle and a quiet and laid-back atmosphere complimented by the open and welcoming local people who call this state their home. 

There are over 80 trails in Maryland, taking explorers on various nature hikes. Many of these trails are easy or moderate difficulty, meaning retirees and those nervous about an intense trek in the woods won't have to worry about many of Maryland's trails. Despite its rural and rustic charm, Maryland is also a very modern location. Many high-quality hospitals and medical centers exist, including UPMC Western Maryland in Allegany County and the famous Johns Hopkins Hospital in Baltimore. No matter where newcomers choose to settle in Maryland, they will never need to sacrifice quality of life, care, and overall atmosphere since this state provides the perfect combination of outdoor beauty and city-scape excitement. 

Bel Air

Bel Air is a northcentral town not far from Baltimore. Initially founded in 1874, settlers came as early as 1731 after issuing a land grant to Daniel Scott. Several small rivers and bodies of water flow near the town's borders, including Heavenly Waters, Plum Tree Run, and Bynum Run. The community perfectly blends natural scenery displayed by sites like Rockfield Park and small-town vibes at locations like Sprouts Farm Market. 

Especially active, nature-loving retirees should check out Ma & Pa Heritage Trail, a five-mile, easy trail ideal for people of all ages. People can also join Ma & Pa Heritage Trail, Inc. in participation with Hartford’s Parks and Recreation. Membership dues help support the care of the trail and other nature sites in Hartford County and allow members to partake in events and meetings. It’s a great way to participate meaningfully in the community and gain new friends. This trail sits on the old site of parts of the Maryland and Pennsylvania Railroad, which provided an access point between the east and the ever-expanding western world of America. 

The Arts and Entertainment district of downtown Bel Air is the site of public and private art displays and live music events. This 98-acre location has an impressive outdoor public art display that anyone can peruse and includes 38 handmade murals and artistic expressions with maps nearby to guide guests around the displays. New residents can get close to townsfolks at Looneys Pub, an Irish-styled eatery and pub with a welcoming and friendly environment with good food and drink. Those who prefer a mellow atmosphere can check out Vagabond Sandwich Company or Bagel Works. Bagel Works is a good breakfast location, whereas Vagabond Sandwich Company is a better location for a brunch date with friends and family.

Havre de Grace

Approximately thirty minutes east of Bel Air is the gorgeous coastal town of Havre de Grace. With its proximity to the Chesapeake Bay and Susquehanna River, Havre de Grace is a great location to experience tranquility surrounded by nature. Tydings Park Island is a small island off the coast of Havre de Grace. It is a lovely location, with the coastal park of Millard Tydings Memorial Park serving as a launching point to the water. This park is a lovely place for a picnic, walk, or explore the local wildlife and history at the Chesapeake Heritage Conservancy.

The small community began officially in 1785. It got its name from the French word for “Harbor of Grace” after the Revolutionary War general Lafayette exclaimed its similarity to the French port town. Most of the city burned during the Revolutionary War, and it suffered several other attacks from the British throughout the conflict. Again, during the War of 1812, the village suffered at the hands of the Engish when the British forces burned almost every structure in town. As a result of the continuous conflicts and burnings in town, very few original structures still stand today, with the notable exceptions of the Concord Point Lighthouse and Saint John’s Episcopal Church. 

The Concord Lighthouse is just a few minutes from Millard Tydings Memorial Park and is one of the town’s oldest structures. This location is a popular spot for tourists, but it’s one of the spots that never gets old, even for locals who visit it regularly. Walking up the lighthouse tower gives a magnificent panoramic view of the bay and neighboring landscape. Havre de Grace has several charming cultural art centers, like the Star Center and the Cultural Center at the Opera House, that give guests and locals a taste of class and talent. Don’t worry; there are plenty of cafes and eateries in town for those who prefer a more mellow and laid-back atmosphere, like Coakley’s Pub and Concord Point Coffee, serving house-roast coffee beverages and homestyle dishes.

Saint Michaels 

Just about two hours south of Havre de Grace is Saint Michaels, a small yet dynamic town along the Miles River. The town boasts a beautiful combination of natural scenery and historic charm, with several parks and well-preserved old sites scattered across its boundary. The town has a stunning view of Miles River, with Muskrat Park being one of the best spots for a beachfront picnic or a stroll along the docks. Marinas, ships, and other maritime pastimes fill the coastline and create a unique opportunity to explore the local wildlife and scenery. This includes sites like Patriot Cruises and Higgins Yacht Yard, where folks can dock their boats or tour the waters on one of the company ships. 

The town’s historic district strives to preserve the community’s heritage by maintaining the old structures and educating those visiting the location. The area dates back to 1972, but the oldest structures here go back to the seventeen and eighteen hundreds. For sea lovers, the site of Oystering on the Chesapeake is a great place to experience the early fishing industry that shaped and sustained the community for years. Not far away is the lovely structure known as the Hooper Strait Lighthouse, which dates back to 1879 and once provided light and safe passage to sailors returning home. 

Residents who love seafood will have lots to enjoy in town at restaurants like The Crab Claw and Foxy’s Harbor Grille. Both sit along the harbor's shore and create fresh, decadent dishes from locally sourced fish, crabs, and other marine creatures. While The Crab Claw only operates during the warmer seasons, Foxy’s Harbor Grille works all year round, so people never need to go without a delicious meal. Many sites are between the inland and coastline, including the Thomas-Kirby House, the Chesapeake Bay Maritime Museum, and Saint Michaels's Nature Trail Covered Bridge, so folks shouldn’t limit their exploration to just the bay.

Easton

Ten miles east of Saint Michaels is the inland town of Easton. The town is near several bodies of water, including Dixon Creek and Tred Avon River, which branches into other rivers and streams. The community offers visitors and residents a taste of two worlds, with its event-filled streets lined with shopping sites and community events, a small-town vibe, and natural scenery. The town began as a Quaker community in 1682 but is a modern and open location ideal for a blend of relaxation and stimulation. The Easton Point Marina and Easton Point Park are not far from the Tred Avon River and are great sites for exploration and daytime excursions. For those with grandchildren, Idlewild Park near the center of town offers a fun time scurrying about the many playgrounds and open areas. 

Grandkids will also love the Be With Me Children’s Museum. This museum combines education and excitement, allowing kids to play real-world scenarios like making a pizza at a pizzeria or fixing a broken vehicle as a mechanic. The best part is it’s an excellent bonding activity for parents and grandparents, who can join in on the activities with their children or grandchildren. But don’t worry, the town offers much more than just a fun time for grandkids. The Academy Art Museum is perfect for budding or expert artists who enjoy looking at fine art displays and want to learn more about honing their skills. The museum offers exclusive benefits to members, as well as relatively affordable art classes. 

The George Murphy Pool in the south of town provides residents with a superb spot to exercise and build lasting friendships with the residents. Thanks to its reputation as a vacation and tourist area, Easton has plenty of good dining experiences. Rude Burger is the place to be if you like homestyle foods like BBQ specialties and American favorites like hamburgers. Rise Up Coffee Roasters is the ideal mix of speed and welcoming vibes for those who prefer a cute cafe where they can start their day. Visitors can either get their cup of joe in a rush or sit and enjoy the restful morning in a wholesome and pleasant environment.

Chesapeake City

Chesapeake City is to the north of Easton, not far from the border of Delaware, and split in two by the Back Creek. It is a preferable location for those seeking a more tranquil environment than sites like Easton. The Chesapeake City Canal is one of the area's most popular and heavily utilized canals, with its original construction dating back to 1824, providing more efficient shipping routes between the east and the early west. The canal is a lovely site to explore, but several bridges worth visiting connect the town and give excellent views of the creek and surrounding areas. 

The canal and Back Creek were essential to the town’s early history and economic development. Land surveyors, like Augustine Herman, were the first to consider the potential of a canal to connect the Delaware River and the Chesapeake Bay in the 1760s. Although the canal took decades, it was eventually built and helped the town grow into a hub of commerce. New residents should take some time to explore the canal and its museum. Not only is it a fascinating location with some spectacular views, but it’s also a vital piece of the community and its cultural heritage. Not too far from the canal museum is the adorable Bethel Bridge Lighthouse, a small white and black lighthouse that adorns the shores of the Back Creek. 

The Ben Cardin C&D Canal Trail is a 15.4-mile long trail that takes travelers along the creek and usually takes about four and a half hours to complete. It's a great trail for people of all ages who want to survey the area's beautiful landscape and get a decent workout that isn’t very difficult since, despite its length, the trail is relatively easy. The Schafers Canal Restaurant and Bar is a delicious place to end the day. Not only do they have excellent food and drinks, but they have fun events everyone can enjoy, including a stunning ballroom.

Saint Mary’s City 

Just under three hours southwest of Chesapeake City is the vibrant and beautiful historic town of Saint Mary’s City. For history and culture lovers, Saint Mary’s City is a never-ending wealth of experiences and well-preserved historic landmarks, homes, and structures. The town’s location along the Saint Mary’s River gives the area a lush, green landscape filled with native plants and wildlife. The Historic Saint Mary’s City Nature Trail takes adventurers on a 3.79-mile trip around these gorgeous nature scapes and typically takes just over an hour to complete. 

Although the community’s natural scenery is worthy of mention, it is not the town's main attraction. The area’s history is the most popular aspect of the city and celebrates the region’s more than 300-year colonial history beginning in 1634. Catholic settlers came to the site of the modern-day town to escape religious persecution and gave the city its name in honor of the Virgin Mary. The region to the south of town is known as the Historic St. Mary's City and gives people an authentic, immersive experience of the life and times of these early settlers. It's a great spot to see a reenactment or witness educational events that help bind the community together in a shared heritage. 

Many old structures still stand in town, including St. John’s Site Museum, the (Reconstructed) State House of 1676, and The Brick Chapel (ca. 1667). St. Mary’s College of Maryland houses the St. John’s Site excavation, which gives visitors a glimpse of an archeological dig and one of the earliest structures in town. The State House was rebuilt in 1934 to celebrate the community's 300th anniversary. It is a free site to visit and occasionally hosts special events for the town. Last, new residents will love visiting the 1667 Brick Chapel, a monument to the city’s faith, with a glass floor where guests can view some of the original lead coffins of settlers. While there are a few restaurants in St. Mary’s City, including Same Same But Different sandwich shop, the area is better known for its historic and natural charm than its shopping experiences.

Cumberland

Nearly four hours northwest of St. Mary’s City is the adorable town of Cumberland, situated along the border of West Virginia and the North Branch of the Potomac River. Its proximity along the Potomac River makes the city an outdoor paradise, with the Western Maryland Scenic Railroad giving people a front-row seat to the surrounding mountains and woodlands. It’s especially spectacular when the leaves change during the fall, but it's fabulous in all seasons. For those who prefer cycling, the Wheelzup Adventure is a place that can satisfy everyone no matter their age, with fantastic views of the pathways along the waterways and various outdoor experiences. They’re focused on promoting an atmosphere of healing and mental well-being, where people can find a sense of belonging and community along the wooded trails of Cumberland. 

Cumberland’s official beginnings started when the general assembly established the town in 1787. However, its history goes back much further, with some experts believing the history began thousands of years ago, as evidenced by the remnants of human settlement. As a historically and culturally rich community, the city offers many local gatherings that help fuel the local spirit and encourage lasting bonds. Sites like the Cumberland Country Club, built in 1919, are popular spots for people to gather and not just play golf. The location is part of the golf course, restaurant, and event center, all within the rolling greens of the country club. Becoming a member here as a new community resident is a great way to make friends and establish lasting roots.

New Market

New Market is a lovely, historic town located near central Maryland, about an hour and a half east of Cumberland. Commonly known as the antique capital of Maryland, New Market is the ideal combination of small-town shops run by residents and welcoming and engaging townwide events. Almost nothing shows the welcoming and close-knit nature of the town more than the annual Christmas events that occur throughout the city. True to its nature, the yearly Christmas Market allows members of the New Market to sell their finely crafted gifts to holiday shoppers. And that’s not all; there’s also the annual Christmas parade accompanied by  Mrs. Claus telling stories and spreading cheer. 

New Market once stood as the main town along National Road, the early highway connecting the east and west. However, a small community of settlers existed in and around modern-day New Market since 1745, although it was not officially established until 1793. There are several lovely locations in town on the National Register of Historic Places, including the town’s historic district, Drummine Farm, and the Henry Nelson House. The Henry Nelson House dates to the early 1800s, although the exact date of its construction isn’t known, and sits just a few minutes outside the town’s borders. The Drummine Farm is also a few minutes outside of town and is a pretty Georgian-style home built in 1790 with several additional structures around the property, like a smokehouse. 

This small town has a few little restaurants and hang-out spots that will make an ordinary evening memorable. Pour Decisions Restaurant and Bar has an eventful atmosphere and live music on certain nights, adding to the site's fun and exciting environment. Or, for more laid-back and classy experiences, the Vintage is the ideal hangout spot. This chic redbrick building is an essential piece of New Market’s past, having served as a general store and a hotel that housed migrants as they moved from east to west. Today, they’re a luxurious place and serve diverse dishes, including Ahi Tuna, caprese, and much more.

Mount Airy

A few minutes East of the close-knit community of New Market is the rural railroad town of Mount Airy. The town’s borders surround several small rivers, streams, and creeks, including Woodville Branch and Bush Creek, located along Old National Pike. The community has plenty of parks and outdoor activities, but the best location is Watkins Park and Watkins Dog Park. These sites not only provide excellent walking trails for people and their four-legged friends, but they’re also lovely spots for picnics, a pavilion to have a small event, and tennis and volleyball courts. 

Mount Airy began as a small settlement of houses and shops along Parr’s Ridge in the 1830s. Around ten years later, the small settlement developed further with the construction of the first church and educational center in 1846. The good news is that this structure remains the Pine Grove Chapel and Cemetery on Main Street today. The place is primarily used for burials today, and the website makes locating the burial site of a loved one or distant relative very easy. It’s worth visiting to better understand Mount Airy's history and heritage, even for those who don’t have relatives in the area. 

The downtown area has plenty of small-town restaurants and eateries that everyone will love. The Upper Deck Sports Bar and Grill is a favorite place for locals to grab lunch or dinner, with the laid-back atmosphere fostering connectivity in a wholesome family location. Those who want to support a local, women-owned business should check out Cle Doree for some delicious pastries. Those hoping to have a fun day shopping at a chic, adorable location should check out the Blossom and Basket Boutique. While they specialize in wedding flower arrangements, they’re a great place to buy a gift for that special someone.

Retire in Maryland's Enchanting Small Towns

Maryland's magical natural charm allows retirees to find a perfectly immersive and soothing place to live out their golden years. For those who want to find a close-knit community, those towns with smaller populations might be the better choice, but those who want a more exciting time should check out the more prominent communities. Maryland has over 16,000 registered small businesses, meaning many of the area's shops and stores are family-owned and operated. This means that almost every experience will likely be met with a personal touch from the state's families. Maryland is the ideal choice for those who hope to have a retirement marked by a tranquil environment where people are friendly and welcoming.