Aerial view of Annapolis, Maryland.

9 Best Places To Retire In Maryland

Retirement is a time to focus on living life fully in a place that offers comfort, community, and opportunities to stay engaged. It’s not just about slowing down but embracing a new chapter filled with beautiful surroundings, friendly neighborhoods, and enriching activities.

Maryland is home to a diverse range of towns and cities that cater to retirees, offering quality healthcare, vibrant communities, and access to nature. From charming coastal villages to serene mountain retreats, these destinations provide the ideal settings for a fulfilling and active retirement.

Annapolis

Downtown view of Main Street with the State House in Annapolis, Maryland.
Downtown view of Main Street with the State House in Annapolis, Maryland.

Perhaps you served in the Navy or military and prefer to retire in a similar environment, or lived inland and desire to retire with a change of scenery. Known as America’s sailing capital, Annapolis’ Naval heritage and ocean activities complete every wish. Steeped in navy history, Annapolis is home to the US Naval Academy, the U.S. Naval Academy Museum, and other popular museums. Besides the ocean, rivers, and creeks banked by gorgeous nature, invite canoeing and kayaking or exploring the charming streets, like Maryland Avenue, lined with historic buildings hosting shops and restaurants for everyone’s tastes and budget. Healthcare is a priority in Annapolis, with several healthcare facilities like the Annapolis Health Center and a community that cares for its residents.

Oxford

Aerial view of Oxford, Maryland on the Chesapeake Bay with clouds, water and shoreline.
Aerial view of Oxford, Maryland on the Chesapeake Bay with clouds, water and shoreline.

Oxford might be a small town, but it’s bursting with life. Picnic and relax at the Town Park alongside the shoreline, sail or kayak, cozy up with a good book from the Oxford Library on rainy days, or learn about Oxford’s 350-year history at the Oxford Museum. The Conservation Park is perfect for everyone, whether active and fit or aspiring to be. It’s perfect for a casual stroll or running and biking. The fresh air blesses the lungs while the wetland’s spectacular scenery and wildlife inspire. Health concerns are cared for at The Oxford Rehabilitation and Healthcare Center. The best part of retiring is making new friends. So, meet new friends at the community center every Monday, Wednesday, and Friday and enjoy conversation and free coffee. When the grandkids visit, and they can ride a bicycle, enroll them in the Oxford Kids Camp for a week (or four) of fun and entertainment.

Ocean City

People walking along the Ocean City Boardwalk in Maryland.
The Ocean City Boardwalk in Maryland. Editorial credit: George Sheldon / Shutterstock.com

Do you enjoy Marlin fishing, golfing, and living by the ocean? Thanks to a hurricane in 1933, an inlet was created, separating Ocean City from Assateague Island. Residents decided to keep it separated and built jetties to stabilize the inlet. This ingenuity is why Ocean City is sought after by retirees and tourists today. However, in summer, it exceeds this by far. So, if the influx of visitors during the holidays and weekends is not an issue, Ocean City is ideal for retirement. Along the shoreline is the boardwalk with three miles of shops, arcades, plenty of seafood restaurants, and the Ocean Gallery. When the family visits, there is much to entertain: Trimper’s Rides and Amusements has entertained for over 100 years. Spend endless hours at the Jolly Roger’s Splash Mountain Water Park or fly a kite on the beach. Hot, humid summers and mild winters mean stunning sunrises. So, dip your feet in the beach sand and watch spectacular sunrises.

Hagerstown

Street view of Hagerstown, Maryland, USA
Street view of Hagerstown, Maryland, USA.

During many battles, such as the First and Second Battles of Hagerstown in July 1863, Hagerstown has preserved its history in its buildings, like the Jonathan Hager (the founder) House Museum or the Vietnam War Veterans Monument. A railroad built after the war revived the town, becoming a significant transportation hub. Visit the City Park Train Hub and learn about the Steam Engine 202 and other trains that influenced Hagerstown’s growth. Diversifying from the battlegrounds, Hagerstown was immersed in the arts and culture scene. The Mansion House Art Center, an 1846 Georgian-style house, the headquarters for the Valley Art Association, showcases local artists’ works. Another outstanding museum embracing Hagerstown’s love for art is the Washington County Museum of Fine Arts. Visit the museums while enjoying a walk in the City Park. The park has several trails for hikers, like the Hagerstown Arboretum Trail, the Founder’s Trail, and the StoryWalk. Hagerstown is a wonderful retirement option for art and history enthusiasts who enjoy a quiet, close-knit community and several excellent healthcare facilities, such as the Meritus Medical Center.

Hyattsville

Street view of Hyattsville in Prince George's County, Maryland
Street view of Hyattsville in Prince George's County, Maryland. By Bohemian Baltimore, CC BY-SA 4.0, Wikimedia Commons

Hyattsville is a historical utopia with its Victorian and colonial homes, and it prides itself on being listed in the National Register of Historic Places. It offers diverse opportunities for becoming involved in a community of arts, culture, and outdoor activities. For art devotees, the Pyramid Art Center hosts workshops in art, printmaking, papermaking, and showcasing local artworks. Release the individuality within when visiting the Vanadu Art House, packed with captivating antiques and junk. It’s an artist’s or collector’s haven. The Anacostia River Park satisfies outdoor cravings to work off those unwanted calories. While burning energy running, walking, or biking on one of many trails, observe the plethora of wildlife, then relax and appreciate the stunning views. Hyattsville's many healthcare facilities, such as MedStar Health Medical Center and West Hyattsville Medical Center, cover every health concern, so relax and enjoy life peacefully.

Cumberland

A scenic view from a hill overlooking the historic town of Cumberland, Maryland
A scenic view from a hill overlooking the historic town of Cumberland, Maryland. Editorial credit: Kosoff / Shutterstock.com

Cumberland overcame its significance during the Civil War, developing into a hub for manufacturing industries and later in technologies and tourism. But do not be deterred. Cumberland is gorgeous and has the surrounding nature of the Appalachian Mountains, like the 150-mile Great Allegheny Passage and the 3000-acre Rocky Gap State Park. After availing of the many hiking trails and water activities Cumberland offers, enjoy a train ride on the Western Maryland Scenic Railroad. It’s not merely a ride through breathtaking scenery but has numerous routes, including a Murder Mystery Dinner Train. Murder mystery dinner is an intriguing concept, yet it's hardly ever on the entertainment list. It’s time to fulfill the fantasy and retire in Cumberland. Learn more about your new home at the Cumberland Museum and Archives via its exhibits, events, and interactive programs. Cumberland might be a small town in the Appalachian Mountains. Still, it has everything desired for a retired life, including excellent healthcare at UPMC Western Maryland and Cumberland Healthcare Center facilities and amenities.

Berlin

Old brick buildings and narrow streets in Berlin, Maryland.
Old brick buildings and narrow streets in Berlin, Maryland. Editorial credit: Kosoff / Shutterstock.com

Maryland’s towns are vibrant, boasting their history. Berlin is no different, but it is also a shopper’s paradise, named Best Town for Shopping in 2018 and 2020 by USA Today and a Top 10 Great American Main Street. Its many shops, galleries, antiques, delectable restaurants, and markets that will keep you shopping for hours. Several streets have interesting murals and hidden stars for a greater shopping experience and more entertaining. However, Berlin is not all about shopping. It has superb and enchanting studios, like Beach Memories, where artists create hand-blown glass jewelry, Henry Fine Arts, and Jeffrey Auxer Glass Design Studio. Musicians should not miss visiting the Harvest Guitar Shop for incredible handmade wooden guitars or relax at the Greyhound Indie Bookstore. Berlin delights in displaying its history at the Calvin B. Taylor House Museum. Take a well-shopped break and enjoy kayaking and exploring coves with Track and Yack's railbike tours. Active retirees will love their new home in Berlin, filling the days with endless sea and shore activities.

Chestertown

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, USA.
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, USA.

Chestertown, Maryland, offers retirees a harmonious blend of historic charm and modern amenities. The town's well-preserved 18th-century architecture and vibrant arts scene, including performances at the Garfield Center for the Arts, provide ample cultural engagement. Healthcare needs are well-served by the University of Maryland Shore Medical Center at Chestertown, which offers services such as a full-service emergency department, medical imaging, and rehabilitation programs. For those seeking a community atmosphere, Heron Point of Chestertown, an affiliate of Acts Retirement-Life Communities, is a 66-acre riverside retirement community that offers stimulating opportunities for physical, mental, cultural, and spiritual well-being. With its combination of historical ambiance, cultural activities, quality healthcare, and recreational opportunities, Chestertown stands out as an ideal retirement destination in Maryland.

Thurmont

Downtown Thurmont, Maryland
Downtown Thurmont, Maryland. Image credit Andrew Bain, CC BY-SA 3.0, Wikimedia Commons

Settled in the Catoctin Mountains, Thurmont is a retiree’s dream. Since it’s surrounded by luscious nature, expect to find amazing wildlife and natural areas, like the 43-acre man-made lake and the 78-foot Cunningham Falls. Satisfy energetic urges by swimming, cycling, or hiking in the many parks. When the grandkids visit, they will be enthralled by the Catoctin Wildlife Preserve and Zoo’s many species. Instead of venturing to the mountains, participate in the Thurmont Community Park’s many events, like the annual Colorfest, Halloween festivities, and movie nights. Like most towns in Maryland, Thurmont played its part in the American Revolutionary War, and the Catoctin furnace, once an iron smelting plant, is open to the public. Thurmont’s Main Street is a hive of activities featuring local artists’ works, crafts, restaurants, and general stores. Healthcare might be a concern for most retirees. However, Thurmont has several healthcare facilities like the Catoctin Medical Group and Evergreen Adult Medicine.

Finding The Ideal Retirement Destination in Maryland

Retirement is more than a transition; it is a chance to craft the life you have always envisioned. Whether drawn to the serene charm of a small town, the energy of coastal living, or the convenience of a vibrant community, Maryland offers a diverse array of options to match every lifestyle. Prioritize what matters most, whether it is access to healthcare, outdoor adventures, cultural experiences, or a peaceful setting, and discover the ideal place to call home. In Maryland, the next chapter is yours to shape and savor.

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