11. Chestertown, Maryland: A Historic Gem on the Eastern Shore
Chestertown, located on Maryland’s Eastern Shore, is a historic town with a population of around 5,252, and one of our favorites on this list of best places to retire. Established in 1706, it boasts a rich colonial history, evident in its well-preserved architecture and vibrant cultural scene. The annual Chestertown Tea Party Festival commemorates the town’s revolutionary past, offering parades, reenactments, and colonial crafts. The town is also home to Washington College, providing educational and cultural opportunities for residents. The scenic Chester River offers boating and fishing activities, appealing to outdoor enthusiasts. With its blend of history, culture, and natural beauty, Chestertown provides a charming setting for retirees.