6 Senior-Friendly Towns in Chesapeake Bay
The Chesapeake Bay is the United States' largest estuary. It encompasses parts of Virginia, Maryland, and the state of Delaware. Many great options exist when deciding to retire in the Chesapeake Bay Area. From urban and suburban cities to small towns, there is more than where to consider. Taxes, housing costs, healthcare availability, and recreation are equally important factors.
The Chesapeake Bay provides an excellent opportunity to enjoy a relaxed lifestyle with umpteen recreational activities amidst natural beauty. If you are looking for a place to settle down, consider these six senior-friendly towns, all in the Old Line State of Maryland.
St. Michaels
St. Michaels is a tranquil, beautiful town popular among seniors because of its charming waterfront views and abundant outdoor activities. The town is located in Talbot County on the banks of the Miles River. The median listing price of housing in St. Michaels is $1 million (according to realtor.com). Seniors can enjoy shopping or dining on Talbot Street, or a day at Muskrat Park. Popular stores include Antiques on Talbot while Harrison’s Harbour Lights is one of the town’s best restaurants. Hollis Park is another popular spot because it is located near the harbor and close to the Chesapeake Bay Maritime Museum.
Cambridge
Like St. Michael’s, Cambridge is a waterfront community steeped in maritime and colonial history. Residents can enjoy visits to the 28,000-acre Blackwater National Wildlife Refuge to bird watch, hike, bike, fish, hunt, and paddle. Another great spot is the Heritage Museums and Gardens of Dorchester which features several lush gardens and museums that showcase the town’s history. The median listing prices of homes is around $290,000.
For healthcare needs, seniors can head to the University of Maryland-Shore Medical Center (formerly Dorchester General Hospital). It is a 47-bed hospital with 24-hour emergency services, lab testing and surgery facilities.
Easton
Located in Talbot County, Easton is a small town with approximately 17,100 residents. The town is quite safe and has brick-paved streets lined with quaint shops, restaurants, and art galleries. The median listing prices of a home in Easton is $524,000. Seniors living in the area can head to Tred Avon River to fish, hike, bike, boat, and kayak.
The Avalon Theater is a town staple and hosts regular educational, cultural, and dynamic art events. Every Thursday to Saturday, the Amish Country Farmers Market is open, offering residents fresh produce, dairy, meat, furniture, and handicrafts.
Oxford
With only about 800 residents, Oxford is a small, rural town in Maryland. The median home listing price in 2024 is 1.6 million. Oxford is one of the first places settled in Maryland and has a rich history. It is also considered a sailing mecca. The Oxford Museum displays artifacts and handicrafts from the 1700s while the Oxford Community Center hosts lectures and theater performances regularly. The Robert Morris Inn is another historical site, it was once the home of revolutionary patriot Robert Morris. The home now functions as an inn and restaurant where residents can dine.
Solomons
Once a busy shipyard and oyster processing center, Solomons or Solomons Island is now a bustling, picturesque resort town. The river boardwalk or Riverwalk along the Patuxent River is beautiful for a stroll. Solomons is well known for its many festivals, including the Harvest Taste of Solomons, Waterman’s Festival, and Solomons Christmas Walk. Most residents own their homes and the median house listing price is approximately $529,000. Hiking, biking, and camping are common activities in Solomons because the town is surrounded by miles of trails and has several parks such as Calvert County-Maryland Co-Op Park.
Chestertown
Nestled in the scenic Chester River Valley is Chestertown, a charming small town with approximately 5,500 residents. Established in 1706, it is one of Maryland’s oldest towns. The median price listing of a home in Chestertown is around $420,000. For healthcare needs, residents can head to the University of Maryland Shore Medical Center. The medical center offers residents a 24-hour emergency department, lab testing, radiology department, and same-day surgery. For outdoor adventures, seniors can spend a day down by Chester River, Betterton Beach, or explore the Eastern Neck National Wildlife Refuge.
Retiring in Chesapeake Bay, Maryland, offers seniors pension exclusions up to $39,000, social security tax exemptions, a low sales tax, and no inheritance tax. Additionally, each town is naturally beautiful, from Hollis Park in St. Michaels to the Eastern Neck Wildlife Refuge in Chestertown. Each has a rich history and culture dating back to the 1700s. These towns offer senior citizens safety, comfort, and modern amenities amidst a peaceful, welcoming community. So, if you are looking for a new place to call home, consider these six senior-friendly towns along Chesapeake Bay.
