14 Gorgeous Chesapeake Bay Towns To Visit In 2023
The Chesapeake Bay is America’s largest estuary, with over 11,000 miles of shoreline straddling parts of six states on the East Coast. It stretches from the Susquehanna River to the Atlantic Ocean and holds approximately 11 trillion gallons of water. Several big cities and small towns have cropped up around the famous watershed, taking advantage of its scenic natural beauty and ample angling opportunities. Besides the multiple water-based activities, the Chesapeake Bay region is dotted with nature preserves, pristine parks, hiking trails, camping sites, and diverse wildlife species worth discovering. It also houses colonial-era villages with a treasure trove of historic landmarks that take you back to the bygone eras. The best way to experience the charm of the sprawling watershed is to visit its less-crowded locations, which place you in the heart of its natural splendor. Here are gorgeous Chesapeake Bay towns you need to visit in 2023.
St. Michael’s, Maryland
A popular vacation hotspot on the Eastern Shore, Saint Michael’s, Maryland, started as a thriving seaport but has since adopted a different personality. Today, it charms visitors with its picturesque waterfronts and an eclectic mix of fun things to do, especially during the summer. The Chesapeake Bay Maritime Museum paints a vivid picture of the region’s maritime heritage through a collection of exhibits, artifacts, and old vessels used on the Chesapeake Bay.
Adjacent to the museum, you’ll come across the 1879 Hooper Strait Lighthouse, an iconic city landmark from the 19th century on Navy Point. One of the best ways to experience the beauty of this quiet Chesapeake Bay town is to get on the water, and booking a tour with Patriot Cruises allows you to enjoy a laid-back trip while soaking in the picturesque scenes.
Solomons Island, Maryland
Solomons Island, or Solomons, is a quaint waterfront town on the southern end of Calvert County, Maryland. Considered among the best tourist spots on the Chesapeake Bay, it boasts a delightful atmosphere and spectacular vistas of the Patuxent River. If you’re interested in the town’s history, there is much to learn at the Calvert Marine Museum. This impressive facility offers a glimpse into Chesapeake Bay’s maritime heritage through exciting artifacts, including one of the few remnant screw-pile lighthouses on the bay.
Another must-visit attraction on Solomons Island is the Annmarie Sculpture Garden and Arts Center, an excellent spot for art enthusiasts and nature lovers. This Smithsonian-affiliated center comprises indoor galleries showcasing intricate art pieces, sprawling lush gardens, and a kid’s natural play area. By hiring a vessel from Solomons Boat Rental, you can embark on a cozy cruise to check out iconic town landmarks like Drum Point Lighthouse. Later, you can sample delicious Chesapeake Bay cuisine at the popular Lighthouse Restaurant and Dockbar.
Cambridge, Maryland
Another popular destination on Maryland’s Eastern Shore, Cambridge, is a historic town teeming with colonial architecture and fun outdoor adventures. You can experience the area’s charm by strolling through its downtown, lined with unique galleries, quaint restaurants, and interesting museums. The Harriet Tubman Museum and Educational Center preserves the legacy of the iconic slavery-era figure and displays artifacts, videos, and literature chronicling the Civil War, Underground Railroad, and Post-Civil War periods.
If you prefer to spend your time outdoors, the Blackwater National Wildlife Refuge is an excellent spot to watch migrating birds and native animal species like the Southern flying squirrel. Alternatively, you can take a kayak tour and paddle down the Choptank River to the historic Choptank River Lighthouse. Meanwhile, those with kids can take them to the Cabin Fever Play Center for a day full of fun and adventure.
Havre de Grace, Maryland
Havre de Grace was named after the French port city le Havre. It is a historic Maryland town situated on top of the Chesapeake Bay and the mouth of the Susquehanna River, offering epic views of the two water bodies. One of its must-see landmarks is the Concord Point Lighthouse, which was constructed in 1827. It has the distinction of being the second oldest lighthouse in the state and currently serves as a popular wedding site, thanks to its picturesque views.
If you have a soft spot for the arts, you can tour the Havre de Grace Decoy Museum to browse a sophisticated collection of duck decoys used in duck hunting and admire the craft that went into the exhibits. Elsewhere, exploring the Susquehanna State Park is an excellent way to appreciate the open spaces in town and take advantage of exciting outdoor opportunities like camping, fishing, hiking, and boating.
Chesapeake City, Maryland
Chesapeake City is easily one of the best Chesapeake Bay towns to visit, thanks to its stunning waterfronts and charming historic district, which features an array of Victorian homes, art galleries, and restaurants. Boat tours are popular among visitors to the town, and hopping aboard the Chesapeake City Tours for an easy-going sunset cruise is a must-have experience, complete with wine and craft beer tastings. But if you don’t want to get on the water, you can admire the views from the historic canal, an excellent spot for a lazy walk.
The vibrant corridor has a delectable dining scene where you can sample delicious seafood. The Schaefer’s Canal House serves tasty seafood, sandwiches, and steaks. Also, the Chesapeake & Delaware Canal Museum is an exciting stop for historians interested in the heritage and operation of the canal linking the Chesapeake and Delaware bays.
Cape Charles, Virginia
This charming little town on Virginia’s Eastern Shore stands out for its gorgeous beaches, Victorian architecture, and walkable downtown. Its cozy atmosphere makes it the perfect destination for a family-friendly getaway, and the 29-acre Cape Charles Natural Area Preserve is an excellent example of the serenity so many come to find in this beautiful locality. Strolling along its long boardwalk takes you through pristine forests teeming with diverse bird species. But if you fancy indoor attractions, the Cape Charles Museum hosts a wonderful collection of exhibits that will paint for you a picture of how Cape Charles and the surrounding area came to be.
Cape Charles is also famous for its bustling seafood scene, and popping into The Shanty allows you to sample fresh delicacies on an outdoor patio while taking in remarkable water views. Alternatively, you can explore the Cape Charles Historic District and take a refreshing dip in the toasty waters of Cape Charles Beach.
Yorktown, Virginia
Yorktown, Virginia, draws tourists with historic charm, as it is among the first shires created in Colonial Virginia in the 17th century. With a modest population of about 300 residents, there is enough room to explore its various historical landmarks and several other attractions. At the American Revolution Museum at Yorktown, you can delve into the influential role that the town played during the American Revolution through immersive galleries, videos, and other exhibitions.
Other prominent historical sites, like the Yorktown Victory Monument and Yorktown National Cemetery, offer a look into what transpired in the town during the Revolutionary and Civil War periods. But if history is not your thing, you can head to Yorktown Beach for a stress-free stroll on the sandy shores and a laid-back lounging session while people-watching.
Easton, Maryland
Easton is also situated on Maryland’s Eastern Shore and wows travelers with a rich past and unique culture. This town has a little bit of something for everyone. If you are a history buff, you will love exploring the many historic structures in the area, housing famous sites like the Academy Art Museum and Talbot Historical Society. To spend some quality time outdoors, Idlewild Park is an exciting 1-acre expanse full of swings, slides, fort, and other play areas, perfect for families.
Meanwhile, The Trippe Gallery in Historic Easton showcases intricate art pieces, including watercolor paintings and fine art photography. The seafood scene is also worth sampling, and one of the best joints to enjoy a crab pretzel or fried oysters is Headwaters Seafood & Grille.
Oxford, Maryland
This picturesque waterfront destination is among the oldest towns in Maryland, having been founded in 1694. Besides its historic allure, which it still retains, the quiet village beckons tourists to sample fun water-based adventures. Yachting Magazine once ranked it as the world’s best waterfront town, which should interest any first-timer. One of the best experiences in the locality involves hopping on the historic Oxford-Bellevue Ferry, believed to be the oldest privately-run ferry service in the country.
Meanwhile, the Oxford Museum preserves Oxford’s heritage as one of the country’s oldest ports, with more history to be uncovered at The Water’s Edge Museum, which tells the story of Maryland’s founding black families. After exploring all the top spots in the town, travelers can refuel at Doc’s Sunset Grille for delicious crab cakes and fried oysters to rejuvenate.
Chestertown, Maryland
Chestertown, a historic college town on Maryland’s Eastern Shore, has a vibrant arts community and a wealth of Chesapeake Bay cuisine. The town has served as the seat of Kent County since the 18th century and boasts a rich past that you can uncover at the Historical Society of Kent County. But to experience Chestertown’s artistic personality, you can catch a riveting performance at the Garfield Center of the Arts at the Prince Theater.
There’s more to experience in the town for outdoor lovers, including the beautiful atmosphere of Wilmer Park. Sitting along the banks of the Chester River, this delightful natural space offers plenty of outdoor opportunities, including the new Aunt Sarah’s Playground. Shoppers can also stop by The Bookplate before leaving town to shop for a nice souvenir.
Smith Island, Maryland
This isolated community in the middle of the Chesapeake Bay intrigues guests with distinctive Elizabethan accents, which have carried on from one of the oldest English settlements in the region. The island features miles of marshland waterways that are perfect for exploring on a kayak, leading you to gems like “Goat Island,” where non-indigenous goats roam freely. Alternatively, you can discover the territory on dry land by hopping on a bike and enjoying the scenes on your way to Rhodes Point.
Another must-visit site on the island is The Smith Island Cultural Center Museum, which sheds light on the culture, history, and everyday life on the island through immersive documentaries, cultural artifacts, and other exhibits. Lastly, your trip to Smith Island won’t be complete without tasting the iconic Smith Island Cake, the state’s official dessert.
Deal Island, Maryland
Home to the popular Skipjack Festival, Deal Island is a quintessential watermen’s town where aquatic activities like oyster harvesting, crab fishing, and boating abound. This 3-mile-long island in Maryland delights visitors with a long-held tradition during the Labor Day weekend, when participants compete in a series of events, such as fishing, swimming, and boat docking. The two-day occasion also features an exciting parade, amusement rides, and lots of food.
History-hungry tourists can explore the Skipjack Heritage Museum, which preserves the historical and cultural heritage of the Skipjack, the country’s oldest working sailing vessel. Also, there are chances to get on the water and hop between the four communities that make up the island: Chance, Deal Island, Dames Quarter, and Wenona.
Crisfield, Maryland
Billing itself as the “Crab Capital of the World,” blue crabs are a prominent feature in this quaint community, and you will come across them wherever you go—in the water, in restaurants, in art galleries, and even in museums. One of the best times to be in Crisfield is during the Labor Day National Hard Crab Derby, when you can join locals in marking a 60+ year held tradition. At the Crisfield Heritage Foundation, guests get a glimpse into the town’s rich historical heritage and that of the surrounding area.
An excellent way to traverse the area will be to take a tour with Tangier Island Cruises, which takes you on a laid-back cruise on the calm waters of Chesapeake Bay, with a chance to discover various hidden gems. Since you are in crab country, it makes sense to sample the local delicacy at the trendy Fisherman’s Grille.
Annapolis, Maryland
Despite being the state capital, Annapolis maintains a small-town feel and lures vacationers to experience its rich history. Popularly known as the “Sailing Capital of the World,” the town’s rich maritime heritage shines through iconic venues like the Annapolis Maritime Museum and Park, which exhibits artifacts, holds educational programs, and stages events dedicated to preserving naval history on the Chesapeake Bay. The city also houses the treasured United States Naval Academy, a must-visit if you’re in Annapolis.
Exploring the lively downtown area is an opportunity to discover a treasure trove of historical gems, including the stunning The Maryland Inn of the Historic Inns of Annapolis. Besides being America’s oldest capitol building in continuous legislative operation, it is an iconic city landmark and one of the most visited sites in Annapolis.
Wrapping Up
The beautiful expanse of the Chesapeake Bay watershed harbors an array of hidden gems that you can discover by visiting the many towns in the area. From historical landmarks and unique cultural attractions to pristine beaches, these charming Chesapeake Bay towns expose you to the unprecedented charm of the region.
