Chesapeake Bay with boats St Michaels, Maryland, USA.

8 Most Comfortable Towns on the Chesapeake Bay for Seniors

Among the shore of the Eastern U.S. lays the largest area on the Atlantic coast, the Chesapeake Bay. Bordered by Virginia and Maryland, the Chesapeake Bay wraps two opposing landscapes into one masterpiece—one reason why it's often so attractive for weekend getaways. On the eastern shore, you will find low views filled with marsh and water views, and on the western coast, you will see the great heights of the Calvert Cliffs. Retirees have the best of both worlds in the heart of these 8 towns on the Chesapeake Bay, not only filled with beautiful surroundings but with recreational indoor activities such as museums filled with rich Maritime history, senior recreational centers, and, best of all, state-of-the-art senior healthcare facilities.

Prettiest Towns To Visit On The Chesapeake Bay These charming locations are like the Bay’s best-kept secrets, where the pace is slower, the smiles warm, and every street feels like it is inviting you to be transported through time.

Havre De Grace, Maryland

Havre De Grace city illuminated by the golden light of dusk. Editorial credit: Wirestock Creators / Shutterstock.com

Havre De Grace, Maryland is an urban district consisting of eight neighborhoods that make up the present town, with buildings that have stood against the test of time for over 200 years. This small town boasts outdoor adventures for seniors who wish to remain active. Havre De Grace Promenade is a scenic boardwalk that overlooks the Susquehanna River, Tydings Park, the Decoy Museum, The Maritime Museum, and one of the largest attractions here, the Concord Point Lighthouse which was added to the town in 1827. Not only does Havre De Grace offer a suburban feel with waterfront views, parks, and relaxing greenery but has many Senior Activity Centers within the area that offer gyms, computers, billiards, and recreational rooms. The town upholds a community tone. Located centrally is the University of Maryland and Medical Center which specializes in geriatric care such as urgent care, orthopedics, cardiology, and many others. As of January 2024, the median housing cost comes in at $489,000, with the median home sold price at $400,000. These numbers are slowly rising; however, Havre De Grace, Maryland remains a very affordable town for seniors. With all of these extracurriculars offering a safe space, it’s no wonder why many seniors are choosing Havre De Grace to retire.

Cambridge, Maryland

Cambridge, Maryland is located in Dorchester County, the largest municipality and one of the oldest colonial cities in Maryland. The town dates back to 1684 along the Choptank River, harboring a maritime culture for seniors filled with Crab and Oyster catching, museums rich with history, and a historic district that contains over 300 years of history. The Richardson Maritime Museum holds many artifacts and the best-kept secrets about building boats. Blackwater National Wildlife Refuge is another popular attraction for seniors in the area and was established in 1933 as a waterfowl sanctuary for migration. Whether you are up for hunting, hiking, paddling or simply going for a scenic drive, there is always an outdoor activity around the corner.

The University of Maryland Shore Regional Health at Cambridge is the primary health service in the area and specializes in senior care. The hospital is open 24/7 and has a telehealth line open for phone calls. The median home value here as of January 2024 is an astonishing $321,031. Not only is this area senior-friendly, with moderate crime rates of 1 in 35 in the south, but extremely budget-friendly.

Chestertown, Maryland

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

If you are looking for one of the most historic parts of the Eastern Shore to retire, Chestertown may be the place for you. If you present yourself as a lifelong learner, Washington College has an Academy of Lifelong Learning program for adults and seniors that stimulates the mind. The Chestertown Spy has newly updated walking tours as well. You’ll be sure to achieve your daily steps exploring the magnificent history of Chestertown.

The RiverArts Studio invites the public to mingle with artists in their creative spaces behind the scenes. This spot is a cohesive mix of a gallery, clay studio, kidsSPOT, and arts education. If you have grandchildren and family who like to visit, there are many options for fun activities. Health services in the Chestertown area include the University of Maryland Medical Center and the DaVita Chestertown Dialysis Center. Services include a focus on long-term palliative care. The average home price here trends upward to $399,000 as of 2024 statistics. Chestertown can enrich your lifestyle with inherent history, a thriving art scene, and educational opportunities knocking at your door.

Easton, Maryland

View from the Thompson Park and the City center of the historic town of Easton. Editorial credit: grandbrothers / Shutterstock.com

Easton, Maryland has been named one of the best small towns in America and is known for its tight-knit community activities, historical nature, and jaw-dropping architecture. Idlewild Park holds many community events and features baseball fields, picnic tables, water fountains, and other amenities. The local Easton farmers market is set up by local vendors on Saturdays, selling fresh produce and handmade items. The Avalon Theatre upholds history to Easton, originally built in 1921 as the Showplace of the Eastern Shore. The theatre hosts musical guests, performing arts, and comedians. The University of Maryland Shore Regional Health offers extensive geriatric care for seniors and a range of in-patient and out-patient services. The median home price has climbed to $339,000, which is still relatively affordable. Easton, Maryland is ideal for retirees and seniors looking for a peaceful small town rich in community with good healthcare services.

Solomons Island, Maryland

A young couple on a pier below the the Solomons Bridge at night. Editorial credit: Alexanderstock23 / Shutterstock.com — A young couple on a pier below the Solomons Bridge at night. Editorial credit: Alexanderstock23 / Shutterstock.com

Solomons Island is located right at the southern tip of Calvert County and is surrounded by maritime culture. The Calvert Marine Museum has collected the pure Maritime heritage of the Chesapeake Bay since 1970 and is one of the most spoken-about attractions in the area. Another is the Annemarie Sculpture Garden and Arts Center, where there is a fun time for any occasion including sculpture walks, year-round exhibits, native gardens, and their well-loved "tree-mendous" trail.

MedStar St. Mary’s Hospital local to Solomon’s Island has received eight “A” grades for patient safety from Leapfrog Groups National Hospital Safety Survey. Their Senior Rehabilitation Services is an outstanding service the hospital offers—which is why many seniors flock to this well-rounded area. A low crime rate in Solomons Island creates a secure atmosphere allowing peace to prevail. The housing market is competitive in Solomon’s Island, with house prices climbing to $579,000 on average. However, many homes sell for far less. This is a well-sought-after area for retirees due to the lovely summer weather, maritime heritage, and activities present.

St. Michaels, Maryland

Some of the shops and stores in St Michaels, MD along the town's main street. Editorial credit: George Sheldon / Shutterstock.com — Some of the shops and stores in St. Michaels, MD, along the town's main street. Editorial credit: George Sheldon / Shutterstock.com

St. Michaels, Maryland holds breathtaking views of the Chesapeake Bay and was at one time a hub for shipbuilding and trade. The Chesapeake Bay Maritime Museum works as a community partner and pours itself back into its residents. If you are a history buff, this museum has ample information on preserving the shipbuilding heritage and is working on new exhibition centers to keep that history alive. As far as exercise and nature go, one of the well-known trails in the area is St. Michael Nature Trail, a 2.5-mile trail that exudes natural beauty. The walkability of St. Michael is extremely high, inducing a healthy lifestyle with serene views.

The low crime rate in the area also adds to St. Michaels's peaceful lifestyle. The nearest hospital in the area is the University of Maryland Shore Medical Center at Easton only a short drive of only 20 minutes. Maryland Shore Medical Center takes good care of its senior citizens, focusing on preventative healthcare. The home value for St. Michaels is trending upwards towards $700,000, as it is a high retirement destination with some of the most desired views of the Chesapeake Bay.

Onancock, Virginia

Onancock VA, USA. Editorial credit: John Blottman / Shutterstock.com — Onancock, VA, USA. Editorial credit: John Blottman / Shutterstock.co

Onancock, Virginia resides on the Eastern Shoreline and encompasses hospitality and small-town culture. The residents of this town enjoy their tight-knit community. Senior discounts can be found at Ker Place Museum, one of the town's historical landmarks, encompassing the town's colonial historical memory. Nature and animal lovers will enjoy SouthEast Expeditions for Eco-Tours in the area provide paddling tours and information to help you identify local wildlife. Senior-friendly outpatient and life-long health services at Riverside Shore Memorial Hospital are in town. The well-equipped health care and peaceful lifestyle in Onancock create the perfect environment for the modern retiree. The most recent median home value is just under $400,000, coming in at $372,000, making it one of the most affordable towns on the Chesapeake Bay.

Kilmarnock, Virginia

Kilmarnock is one of the smaller towns in both Virginia and the larger Chesapeake Bay area, with a population of roughly 1,500. The rural area includes panoramic waterfront views of Chesapeake Bay and an impressive small-town hub with great food. Many local events from farmers markets, carnivals, and festive holiday celebrations happen downtown. If you are religious, the town has a National Historic Landmark Church, The Historic Christ Church, built in 1735. Or if nature is more up your alley, the Rappahannock River runs through the town. Rappahannock General Hospital, named after the famous River, provides a long list of healthcare services, specializing in senior long-term health. The most recent home statistics come in at $354,000, dubbing it, like Onancock, one of the most affordable places along the Chesapeake Bay area.

Spend Your Golden Years on the Chesapeake Bay

Each of these 8 towns encompasses an array of wildlife, attractions, affordability, and communal senior living. Whether you would like more of a quiet town life or a larger on-the-go full of events life, these places each offer something special that can cater to your needs. One benefit of each town is amazing healthcare facilities are nearby, allowing safety and security in each environment. Picking where to settle down is not easy, however, these towns near the Chesapeake Bay take the edge off.

Share