
8 Best Towns In Chesapeake Bay For Retirees
The Chesapeake Bay areas of Maryland and Virginia are filled with quaint, small, historic towns that offer the perfect destination for retirees. Towns along the Bay's shores are popular among all ages, especially senior citizens, for their natural beauty, welcoming atmospheres, and affordability.
The towns described below are all ideal for retirees as median home values fall near or under the state averages. Yet, they offer ample nature, history, and opportunities to cultivate community in later years. Read on to discover the other advantages these Chesapeake Bay towns hold for retirees who decide to relocate there.
Chesapeake City, Maryland

Sitting along a working commercial canal, where the Chesapeake Bay connects with the Delaware River, Chesapeake City, Maryland, is a unique small town with a population of fewer than 800, 16% of whom are over the age of 65. This quaint waterside town is one of the most breathtakingly beautiful towns in Cecil County. A parade of cargo ships and vessels still travels through the Chesapeake and Delaware Canal on a daily basis. Stop for unique gifts at The Mercantile at Back Creek and enjoy waterfront dining at the Chesapeake Inn or Schaefer's Canal House.
Median home values here are $403,680, under the state average. Public transportation is available in Chesapeake City through Cecil Transit shuttle buses, which can take riders to nearby Elkton and other parts of Cecil County. Should the need for retirement living arise, the Village of Cecil Woods provides mobile home independent living 10 miles away on the outskirts of Elkton. Abbey Manor Assisted Living is also nearby, if more closely monitored care is needed. Medical care can be found at ChristianaCare Union Hospital in Elkton, six miles up the road from Chesapeake City.
Onancock, Virginia

Founded as a port town in 1690, Onancock, Virginia, was described by Captain John Smith as "the gem of the Eastern Shore." The waterside town has a population of just over 1,150, almost 25% of whom are over 65. It is situated in the harbor along Onancock Creek, which flows into the Chesapeake Bay. Median home values here are $287,865, well below Virginia's state average. Visit art and jewelry shops like Ten Good Sheep and C D Marsh Jewelers, or enjoy live performing arts at the North Street Playhouse. The Charlotte Hotel and Terra Mare Restaurant are popular spots for locally sourced seafood and farm-to-table dishes.
Onancock's residents (as well as visitors) can use public transportation through STAR Transit, providing connections with other Virginia Eastern Shore communities. The Onancock Ferry takes riders to nearby Tangier Island, Virginia. One of the largest independent and assisted living communities in the area, Commonwealth Senior Living at the Eastern Shore, is in Onancock. Medical services are provided to the town's residents and visitors by Riverside Shore Memorial Hospital in Onancock.
Snow Hill, Maryland

Another historic Chesapeake Bay town, Snow Hill, Maryland, was chartered in 1686 and is described as being centrally located between beach and bay, river and trails. Of its more than 2,2300 residents, almost 20% are over age 65. Median home values here are $301,055, less than the state average. The small town has a welcoming feel, with many independent shops to peruse, such as Sassy Girl Boutique, and plenty of eateries, including Elliott's Tavern, Puerto Real Tacos & Cantina, and Tides & Vine Wine Bar.
Shore Transit provides residents with public transportation via regional buses traveling through Somerset, Wicomico, and Worcester counties. Retirement homes in Snow Hill include Pleasant Manor for independent living and Marilyn's Home for the Aged for assisted living. Atlantic General Hospital in Berlin, about 16 miles away, is the nearest hospital for medical care.
Melfa, Virginia

Located on Virginia's Eastern Shore, in the Chesapeake Bay watershed, the tiny town of Melfa has a population just under 400, with 17% over age 65. Median home prices here are $248,647, well under the state average. Those who live in Melfa enjoy the quiet, rural town atmosphere with little traffic. Eastern Shore Community College in Melfa offers tuition assistance for senior citizens interested in taking classes. Shoppers may enjoy Melfa's Uniques and Antiques on Main Street, as well as Emmanual Store, which serves breakfast and lunch.
Public transportation is available to the surrounding area via STAR Transit. The ferry at nearby Onancock can take interested riders to Tangier Island, Virginia. And Accomack County Airport, a regional airport, is also located in Melfa. If retirement homes are needed, Commonwealth Senior Living at the Eastern Shore provides independent and assisted living in Onancock, just six miles away. Medical care is given at Riverside Shore Memorial Hospital, also a short ride away in Onancock.
Crisfield, Maryland

Founded on the Tangier Sound in 1666, the waterfront village of Crisfield, Maryland, is the southernmost town in Maryland. With about 2,500 residents, more than 18% of whom are over 65, the close-knit town is known as the crab capital of the world. It is highly conducive to retirement living, with home prices averaging a very affordable $158,176. Annual events such as the J. Millard Tawes Crab and Clam Bake in September foster the neighborly atmosphere in town. Small shops in town, like Tim & Doris's Country Store and The Bay Gift Vault, are welcoming to both visitors and residents.
Public transportation in Crisfield is available through Shore Transit, whose regional buses run through Somerset, Wicomico, and Worcester counties. When it comes to retirement living in Crisfield, Chesapeake Cove provides assisted living, and Alice B. Tawes Nursing and Rehabilitation Center offers more supervised care. McCready Memorial Hospital in Crisfield serves the area's medical needs.
Poquoson, Virginia

Just over 12,600 people live in the town of Poquoson, which is in the Hampton Roads area on the Virginia Peninsula of the Chesapeake Bay, with 20% over age 65. The town, established in 1631, was named the Best Affordable Suburb in Virginia by Bloomberg Business Week. Median home prices here are slightly higher than the state average, at $437,000. This thriving town is the ideal retirement destination and has plenty of opportunities to shop, including Poquoson Gifts, Beachy Bull, and the Poquoson Commons Shopping Center. Residents also enjoy eating and drinking at 6131 Burgers Bourbon & Brew, right in town.
Hampton Roads Transit serves the town of Poquoson's public transportation needs. Dominion Village at Poquoson provides both assisted and independent retirement living options. And Riverside Medical Center in Newport News is the closest hospital, just six miles away.
North East, Maryland

North East, Maryland, is a small village at the head of the North East River, which connects to the Chesapeake Bay. It was founded in 1658 and today has a population of just over 4,100, with about 10% over age 65. This charming town draws thousands of tourists during boating season but remains a tight-knit community, appealing to many retirees. Median home prices are just under the state average, at $392,240. The highly walkable Main Street in North East is notable for its many shops and eateries, including Silver and Sassy, 5 & 10 Antique Market, Woody's Crab House, Chesapeake Bay Coffee Co., and Casa Mezcal.
Public transportation is available in North East through Cecil Transit, whose shuttle buses take riders all over Cecil County. Retirement options include Victoria Park, which offers independent living apartments for seniors. Autumn Lake Healthcare at Calvert Manor provides nursing and rehabilitation services in Rising Sun, just 10 miles north of town. The closest hospital to North East is ChristianaCare Union Hospital in Elkton, also just 10 miles away.
Eastville, Virginia

The town of Eastville, Virginia, is at the southern tip of the Delmarva Peninsula on Virginia's Eastern Shore. It has been the Seat of Northampton County since 1680 and today is home to around 300 residents,18% of whom are over age 65. Home prices average a reasonable $299,675, well under the state median. Residents enjoy the downtown area and its shops including Barrier Islands Salt Company and Margaret's Gifts. Yuk Yuk & Joe's and Buttercups, Biscuits, & Bagels are both popular breakfast and dinner spots.
STAR Transit provides public transportation for Eastville and to other communities in Northampton and Accomack counties on Virginia's Eastern Shore. The nearest retirement home is Commonwealth Senior Living at the Eastern Shore, providing both independent and assisted living in Onancock, about 30 miles north of Eastville. Likewise, the nearest hospital is Riverside Shore Memorial Hospital in Onancock, 27 miles from Eastville.
Retire to the Charm of the Chesapeake Bay
Retiring to the Chesapeake Bay is the dream for many who love the water and want to spend their golden years as close to it as possible. Even for those who are not boaters, retiring to any of these eight towns and their natural beauty can give you great peace of mind. Whether you choose the small-town charm of waterfront towns like North East, Maryland, or prefer a larger but still suburban area like Poquoson, Virginia, relocating to any of these welcoming, close-knit towns can make retirement even more fulfilling.