12 Best Chesapeake Bay Towns For Retirees
Retirees looking for a peaceful, coastal lifestyle filled with charm, natural beauty, and culture may find that the Chesapeake Bay is their ideal destination. The Bay contains quaint waterfront towns featuring the perfect blend of relaxation and recreation, from boating and fishing to checking out historical landmarks to partaking in cultural events. Each community along the shores of the Chesapeake Bay has its own unique appeal, including historic streets, friendly neighbors, and stunning sunsets over the water. These are 12 of the best Chesapeake Bay towns offering retirees the perfect mix of comfort, leisure, and scenic living.
Annapolis, Maryland
Although Annapolis is the capital of Maryland (and the county seat of Anne Arundel County), it has a small population of 40,800. Annapolis may be the perfect Chesapeake Bay location to which to retire if you are looking for a waterfront town with large-city amenities. Annapolis sits at the mouth of the Severn River on the western side of the Chesapeake Bay and is seven square miles in area. It is just 40 minutes from Baltimore and 50 minutes from Washington, DC.
Retirees who are into history may enjoy touring the Maryland State House, the oldest state house in the US still being used by the legislature. The Annapolis Maritime Museum and Park features exhibits on the rich maritime heritage of the area and the ecology of the Chesapeake Bay, as well as a 12-acre park with trails. Seniors wishing to socialize with their peers should check out the Annapolis Senior Activity Center. If medical needs arise, Luminis Health Anne Arundel Medical Center is located right in town.
Cambridge, Maryland
Cambridge, Maryland, home to about 13,000 people, is in Dorchester County on the Choptank River, an estuary leading to Chesapeake Bay. This waterfront town's advantages include a low cost of living and access to water-based activities, as well as to nature. Salisbury, about 40 minutes away, is the nearest city to Cambridge.
Blackwater National Wildlife Refuge, with over 20,000 acres, five miles of hiking trails, and 17 miles of paddling trails, will interest retirees who love spending time outdoors. The Harriet Tubman Museum & Educational Center is a great place to learn more about an important woman in history who called the Cambridge area home. Medical care is conveniently provided in Cambridge by the Emergency Center at University of Maryland Shore Regional Health.
Cape Charles, Virginia
The small town of Cape Charles, Virginia, population of around 1,200, in Northampton County, sits on a peninsula at the southern tip of Virginia's Eastern Shore. It contains the only free public beach on that shore, the Cape Charles Town Beach on the Chesapeake Bay, which is attractive to many retirees who want to live near the water but not pay for beach access. The nearest city to Cape Charles is Norfolk, about 44 miles away.
Nature-loving retirees should check out the Eastern Shore of Virginia Wildlife Refuge, one of the most popular stopping places for migratory birds and insects. While Cape Charles does not have its own senior center, many seniors enjoy gathering at the Cape Charles Memorial Library. Riverside Cape Charles Medical Center is conveniently located in town when medical care is needed.
Chestertown, Maryland
Sitting on the banks of the Chester River, a tributary that flows into the Chesapeake Bay on Maryland's Eastern Shore, the Kent County town of Chestertown houses about 5,500 people. This waterfront town offers retirees a slower pace of life within a strong community. Annapolis is 48 miles away.
The Port of Chestertown Marina features 15 dedicated transient boat slips for retirees who want to keep their watercraft nearby. Washington College, a private liberal arts college, stages performances and hosts events such as theatre, music, and library readings on campus that may interest seniors. The Amy Lynn Ferris Adult Activity Center in Chestertown welcomes seniors age 60 and up. Medical care can be obtained at the University of Maryland Shore Medical Center in Chestertown.
Crisfield, Maryland
The town of Crisfield, Maryland, population 2,500, is in Somerset County on Tangier Sound, an arm of the Chesapeake Bay. This historic waterfront town was founded in 1666 and is the southernmost town in Maryland. It is also known as the "crab capital of the world." Crisfield is an ideal town for retirees who want a quiet, water-oriented lifestyle. The town of Salisbury is the nearest larger town, about 30 miles away.
Since Crisfield is such a historic town, retirees who relocate there may wish to partake in the Port of Crisfield Escorted Walking Tour, with a knowledgeable tour guide narrating the history of the town. Crab lovers will enjoy the crab capital of the world's Tawes Crab & Clam Bake, held each year mid-summer. The Crisfield MAC Senior Center is a great place for retirees to gather with others their own age. The McCready Memorial Hospital in Crisfield has medical care available if needed.
Easton, Maryland
The county seat of Talbot County, on the Eastern Shore of Maryland, Easton sits at the head of the Tred Avon River, a tributary of the Choptank River, which flows into the Chesapeake Bay. This town of about 17,000 was established in 1710. Easton is a quaint and charming historical town that will appeal to retirees who appreciate colonial-style architecture and lively activities. Easton is about 68 miles from Baltimore.
The Talbot Historical Society Gardens occupy one acre in downtown Easton and feature mature boxwood, a shade garden, a perennial garden, and more. Every November, Easton hosts the Waterfowl Festival, which draws bird lovers, artisans, and craftspeople from all over. The Talbot County Senior Center provides services and activities for those aged 60 and up. Easton's own University of Maryland Shore Medical Center is in town for medical care, when required.
Havre de Grace, Maryland
Meaning "Port of Grace," the Harford County town of Havre de Grace, Maryland, sits at the mouth of the Susquehanna River and the head of the Chesapeake Bay, Home to about 14,800, retirees will love Havre de Grace's relaxed atmosphere, waterfront access, and historical sites. It is just 37 miles from Baltimore.
The Promenade, along the Susquehanna River, is a 3/4 mile boardwalk that provides awe-inspiring views of the river as well as its natural inhabitants. The Maritime Museum explores Havre de Grace's waterfront history and its importance to the Chesapeake Bay. The Havre de Grace Senior Activity Center serves senior citizens in the area. The nearest hospital is the University of Maryland Upper Chesapeake Medical Center in Bel Air, just 15 miles away.
Mathews, Virginia
The county seat of Mathews County, the tiny town of Mathews, Virginia, population 500, sits on a peninsula along the western shore of the Chesapeake Bay, on the middle peninsula of Virginia. It has waterfront access on both the Chesapeake Bay and the Mobjack Bay. This village has no stoplights, and may be appealing to retirees who want to truly experience small-town life. Mathews is about 70 miles from Norfolk.
Even though Mathews is small, it still has its share of arts and culture, evidenced by art galleries such as Art Speaks. The community enjoys gathering at the Mathews Farmers Market on Saturdays from April through October on the town's Historic Courthouse Green. The Mathews Active Lifestyle Center senior citizen center welcomes seniors to participate in its activities, with no age requirements. Although Mathews is small, it provides medical care through its Riverside Mathews Medical Center clinic.
North East, Maryland
The waterfront town of North East, Maryland, population 4,000, is in Cecil County at the head of the North East River, which flows into the Chesapeake Bay. Founded in 1658, North East is known for its walkable Main Street that is filled with cute shops, charming coffee houses, and restaurants ranging from casual to fine dining. Retirees who move to North East will surely find plenty to keep them occupied. North East is about 57 miles from Philadelphia, Pennsylvania and 47 miles from Baltimore.
Seniors enjoy gathering at Chesapeake Bay Coffee Company for coffee, fresh baked goods, and companionable conversation. The North East Community Park, 10 acres along the North East River, has paved walkways and plenty of area for picnicking. Cecil County Public Library's North East Branch is recently renovated and offers meeting areas and community gathering spaces for residents of all ages. Medical care, if needed, can be found at ChristianaCare Union Hospital in Elkton, just 10 miles away.
Onancock, Virginia
Onancock, Virginia, with a population of around 1,100, is situated on Virginia's Eastern Shore in Accomack County, along Onancock Creek, which flows directly into the Chesapeake Bay. Captain John Smith called Onancock "the gem of the Eastern shore." The town was chartered in 1608 as a port town. Retirees today will savor Onancock's quiet, waterfront splendor. Onancock is about 50 miles from Crisfield, Maryland, and 40 miles from Cape Charles, Virginia.
Culture-loving retirees can enjoy live theater at the North Street Playhouse. They may also wish to hop on the Tangier Onancock Ferry, with daily runs to Tangier Island from May through October. Central Accomack Senior Center provides services for seniors aged 60 and older. Riverside Shore Memorial Hospital in Onancock is available for medical care as needed.
Poquoson, Virginia
The independent city of Poquoson, Virginia, population around 12,000, is not located in a county, but is within the Hampton Roads area on the Virginia Peninsula of the Chesapeake Bay. Poquoson contains 84 miles of shoreline along the Chesapeake Bay, and was established in 1631 as a fishing village. The Oxford Run Canal Trail is a 1.4-mile walking trail around City Hall towards Wythe Creek Road in Poquoson. It is described as scenic and relaxing, perfect for retirees. The Poquoson Museum is of interest to those who want to learn more about the waterfront town's rich history. The Poquoson Senior Center is held in the Municipal Park Community Center and welcomes seniors age 60 and up. Riverside Regional Medical Center is in Newport News, just six miles away, if medical care is required.
St. Michaels, Maryland
The waterfront town of St. Michaels, Maryland, is located in Talbot County along the Miles River, which flows into the Chesapeake Bay. Retirees enjoy St. Michaels' tranquil waterfront lifestyle, rich maritime history, and strong sense of community. Baltimore is just around 80 miles away from St. Michaels. The Chesapeake Bay Maritime Museum explores the fascinating history, environment, and culture of the region. Retirees looking for a bit of exercise may wish to hit the St. Michaels Nature Trail, a 1.3-mile-long rail trail running through town. The Bay Hundred Senior Center, located in the Perkins Family YMCA, provides activities and services for seniors aged 60 and over. Medical care can be found at the University of Maryland Shore Medical Center in Easton, just eight miles away.
Find Your Retirement Home Along the Chesapeake Bay
These 12 Chesapeake Bay towns offer retirees a blend of relaxation, lively activities, and peaceful waterfront solitude. They are ideal for those who wish to get away from it all and enjoy the natural environment, yet still be close enough to access amenities and activities when desired. Many of Virginia and Maryland's Chesapeake Bay towns provide a lower cost of living, tax benefits, outdoor recreational opportunities, and cultural experiences that retirees won't want to miss.
