7 Most Idyllic Small Towns in the Chesapeake Bay

Chesapeake Bay is known as the largest estuary in the United States and is home to more than 3,000 species of plants and animals. It is bordered by many states, including Virginia and Maryland, and was formed by melting glaciers more than 10,000 years ago. It has now become a haven for fishing, boating, sailing and other water sports such as kayaking. The bay is also surrounded by cute little towns and there is no shortage of places to spend a weekend, whether you’re looking for sandy beaches, calm waters or prime casting grounds. So there’s something for everyone, from shopping in Annapolis to historic sights in Chestertown.

Annapolis, Maryland

View of the Annapolis Harbor in Annapolis, Maryland.
Waterfont buildings and a boat docked along the Annapolis Harbor in Annapolis, Maryland.

Less than an hour’s drive from Baltimore, Annapolis is a waterfront city near many attractions and amenities. Most visitors head straight to the water to enjoy skipjack tours, sailing cruises, parasailing, paddle boarding, kayaking and jet skiing. One can also fish for crab, oysters and shrimp. Back on land, tourists satisfy their shopping cravings by stopping at the farmer’s market or visiting the Arundel Mills Outlet Shopping Mall, with stores like Coach, Bass Pro Shop and Lego. You can also stroll through the historic city center, where you will find coffee shops, pottery studios, bookstores, comic shops, antique shops and tea and spice shops. After all the fun, end the day with a drink along the Annapolis and Anne Arundel County Craft Brewery Trail, with stops like Chessie’s Wharf, Forward Brewing, Crooked Crab and the Guinness Brewery.

Chestertown, Maryland

Aerial view of Chestertown, Maryland.
Aerial view of the coast along Chestertown, Maryland.

A historic town on the Chester River, Chestertown has a deep-rooted Civil War history. History buffs head straight to the Sumner Hall Museum to learn about the backstory, or visit the Bordley History Center to learn about the county’s past. The city is also full of art galleries, performing arts venues and an old-fashioned main street. Visitors can find record shops, chocolate shops, florists, pet shops, bakeries, bars and creameries here.

On warmer days, locals enjoy spending time at the farmers market, which sells soaps, baked goods, produce, meats, dairy products and more. As for parks, plan a picnic at Fountain Park or walk through Wilmer Park, which is right on the water. The Chestertown Marina also has a public boat launch and gas station for those interested in hitting the waves. Reenergize after a trip to one of Chestertown’s many restaurants, such as the Chester River Wine and Cheese Company.

Oxford, Maryland

Boats docked along the harbor in Oxford, Maryland.
Boats docked along the scenic harbor of Oxford, Maryland.

One of the oldest cities in Maryland, Oxford is located on the Tred Avon River and offers plenty of waterfront options. For example, tourists can take a ferry from the city to Bellevue, a neighboring community. Those who want to enjoy the view can also enjoy a meal at the Capsize Waterfront Grill or Docs Sunset Grille, which features an outdoor bar. Or walk through one of the marinas and admire the sailboats, yachts and other watercraft.

The attractions change in central Oxford, and you can enjoy shopping in bookshops, delicatessens, creameries and general stores. Accommodation is also great, as Oxford is full of quaint bed and breakfasts, inns and boutique hotels such as Sandway Suites & Beach. Additionally, if you take a look at everything available in town, there are several other attractions nearby, such as the communities of Trappe, Williamsburg, and Easton.

Cape Charles, Virginia

Aerial view of the coast at Cape Charles, Virginia.
Aerial view of the coastline and waterfront homes in Cape Charles, Virginia.

Cape Charles is a picturesque town in the middle of the Chesapeake Bay. Tourists come here to enjoy sandy beaches perfect for swimming and calm waters for paddleboarding, kayaking and kiteboarding. Those who bring their own boats can take advantage of the public boat launch for a fun time on the water. Even if you don’t have one, companies like Poseidon Watersports offer the opportunity to rent jet skis, boats and bicycles.

In town, visitors and locals alike stroll the beautiful Main Street, which is home to an abundance of unique businesses. A hotspot is the Cape Charles Coffee House, where you can enjoy a delicious iced latte while strolling the streets and walking along the waterfront. There’s also no shortage of restaurants for a good meal, from pizza at Deadrise Italian Kitchen to seafood at Beach Market. At the end of the day, book a room at Cape Charles’ Bay Haven Inn for a comfortable stay in rustic decor.

Saint Michaels, Maryland

St. Michaels Harbor in St. Michaels, Maryland.
A boat docked along Saint Michaels Harbor in Saint Michaels, Maryland.

Saint Michaels is a cute waterfront town on the Miles River and next to Eastern Bay, perfect for shopping, relaxing and exploring. Shopaholics love the Christmas Shop, where they can feel festive all year round. Nearby, you can also stop at a boutique clothing store, browse antiques, or admire artisan crafts and art. After walking around, local restaurants such as the Blue Crab, Fool’s Lantern and Crab Claw entice weary tourists with their delicious seafood, drinks and ambiance.

In addition to the busy streets of Saint Michaels, the city’s seaside location makes for some fantastic activities. For example, experience the tranquil waters of Miles River with a cruise with Patriot Cruises. They offer a range of unique options including a history cruise, a musical cocktail cruise, and group tours. Visitors can also go oyster catching for a new experience in this charming Maryland town.

Chesapeake Beach, Maryland

Bayside Trail in Chesapeake Beach, Maryland.
Bayside Road along the coast in Chesapeake Beach, Maryland. By Famartin – Own work, CC BY-SA 4.0, Wikimedia Commons.

As the name suggests, Chesapeake Beach is a cute little town on the shores of Chesapeake Bay. It’s a great weekend destination in the state, just an hour’s drive from Baltimore and Washington, DC. Upon arrival, tourists delight in the public boat launch, where they can participate in kayaking, canoeing, paddle boarding, and water fishing. Speaking of fishing, the city is a hub for fishermen thanks to its range of fish species such as red drum, black drum and kingfish. Next to the harbor is the Chesapeake Beach Water Park, which offers activities for the whole family. Activities range from floating down the lazy river on a raft to racing on the water slides, which provide a quick glimpse of the tranquil bay.

Visitors who want to stay on land can head to the Historic Heritage Trail, which offers walking paths leading to the Railroad Museum and Bayfront Park. Another option nearby is the Railway Trail, which follows an old railroad line along Fishing Creek. For dinner you can choose from a variety of dishes, such as freshly caught crab, pizza or a classic bar and grill. If this isn’t enough, you can continue your trip in the adjacent community of North Beach, which offers sandy beaches and rentals such as beach chairs, umbrellas and floaties.

Stevensville, Maryland

A historic farm and home in Stevensville, Maryland.
A historic home and farm in Stevensville, Maryland. By JERRYE & ROY KLOTZ, MD – Own work, CC BY-SA 4.0, Wikimedia Commons.

A creative haven, Stevensville is located on Kent Island and is connected to the Maryland mainland by the William Preston Lane Jr Memorial Bay Bridge. Not only is this bridge a famous landmark, but it also provides easy access from Annapolis and a quick connection to Baltimore. Visitors from these cities love Stevensville’s lively streets, full of independent galleries and art stops. It’s also home to an art market, making it even easier to get to know all the local vendors. If anyone wants to hone their artistic skills, Creatives Corner offers classes and workshops, such as graffiti art and cheese making. Hand in hand with the vibrancy, the historic city center also features rustic buildings, which are now protected and available for photos and tours. Such places include the 19th century Old Post Office, the 1902 Stevensville Train Depot, and the 1903 Stevensville Bank.

In addition to the static attractions, visitors should also consider what events may take place during their visit. For example, Kent Island Day in May brings together authors, artists and vendors. This June, join us for Paint Stevensville, where local painters showcase their talent. Also come to the Classic Car Show in November. You can also take in all the sights in one go by taking to the skies on Delmarva Hot Air Balloon tours for an unforgettable experience in Maryland.

Easily accessible from nearby cities such as Washington, DC, Baltimore, MD and Norfolk, VA, Chesapeake Bay offers endless opportunities for waterfront fun. Tourists can choose from more populated cities with all the amenities they need, such as shopping centers and water parks, or spend some time in scenic areas to de-stress and embrace history. Whatever you want to experience, you’re sure to find the perfect retreat in this scenic retreat shared by Maryland and Virginia.