7 Most Idyllic Small Towns in Chesapeake Bay
Famed as the largest estuary in the United States, Chesapeake Bay is home to over 3,000 species of plants and animals. Bordered by many states including Virginia and Maryland, it was formed over 10,000 years ago by melting glaciers and has now become a haven for fishing, boating, sailing, and other water sports like kayaking. The bay is also surrounded by adorable small towns and there is no shortage of places to spend a weekend, whether you're looking for sandy beaches, calm waters, or prime casting territory. Thus, there is something for everyone, from shopping in Annapolis to historical attractions in Chestertown.
Annapolis, Maryland
Under an hour's drive from Baltimore, Annapolis is a waterfront town near many attractions and amenities. Most visitors head straight to the water to enjoy skipjack tours, sailing cruises, parasailing, paddleboarding, 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 farmers' market or visiting the Arundel Mills Outlet Shopping Mall, which features stores like Coach, Bass Pro Shop, and Lego. One can also stroll the historic downtown, home to coffee shops, pottery studios, bookstores, comics, antiques, and tea and spice shops. After all the fun, the best way to end the day is with drinks along the Annapolis and Anne Arundel County Craft Brewery Trail, with stops such as Chessie’s Wharf, Forward Brewing, Crooked Crab, and the Guinness Brewery.
Chestertown, Maryland
A historic small town on the Chester River, Chestertown has a deep-rooted history in the Civil War. History enthusiasts head straight to the Sumner Hall Museum to learn more about its backstory or visit the Bordley History Center to learn about the county's past. The town is also full of art galleries, performing arts venues, and an old-fashioned Main Street. Visitors can find record shops, chocolate shops, florists, pet stores, bakeries, bars, and creameries here.
On warmer days, locals love to spend their time at the farmers' market, which sells soaps, baked goods, produce, meats, dairy, and much 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 fuel station for those interested in getting out on the waves. Recharge after an outing at one of Chestertown’s many restaurants, such as the Chester River Wine and Cheese Company.
Oxford, Maryland
One of the oldest towns in Maryland, Oxford rests along the Tred Avon River, providing ample waterside opportunities. For example, tourists can take a ferry from the town to Bellevue, a neighboring community. Those who want to enjoy the views can also have a meal at the Capsize Waterfront Grill or Docs Sunset Grille, which features an outdoor bar. Or walk one of the marinas and admire the sailboats, yachts, and other watercraft.
The attractions change in downtown Oxford, and one can enjoy shopping at bookstores, delis, creameries, and general stores. Accommodation is also fine, as Oxford is full of quaint bed and breakfasts, inns, and boutique hotels like the Sandway Suites & Beach. Moreover, if you go through everything available in town, several other points of interest are nearby, such as the communities of Trappe, Williamsburg, and Easton.
Cape Charles, Virginia
Cape Charles is a scenic town located right in Chesapeake Bay. Tourists flock here to enjoy sandy beaches perfect for swimming and calm waters that allow 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 your own, companies like Poseidon Watersports provide the option to rent jet skis, boats, and bicycles.
In town, visitors and locals walk down beautiful Main Street, which boasts a plethora of unique businesses. A hotspot is the Cape Charles Coffee House, where one can relish a delicious iced latte while browsing the streets and walking alongside the waterfront. There is also no shortage of restaurants for a proper meal, from pizza at Deadrise Italian Kitchen to seafood at Beach Market. As the day ends, book a room in the Bay Haven Inn of Cape Charles for a comfortable stay amidst rustic decor.
Saint Michaels, Maryland
Saint Michaels is an adorable waterfront town on the Miles River and next to Eastern Bay, perfect for shopping, relaxing, and exploring. Shopaholics adore the Christmas Shop, where they can feel festive all year round. Nearby, one can also stop at a boutique clothing store, browse through antiques, or admire artisan crafts and art. After walking around, local restaurants like the Blue Crab, Fool’s Lantern, and Crab Claw beckon weary tourists with their delectable seafood, drinks, and ambiance.
Beyond the bustling streets of Saint Michaels, the town’s coastal location makes for some fantastic activities. For example, experience the tranquil waters of Miles River with a cruise at 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 fresh experience in this charming Maryland town.
Chesapeake Beach, Maryland
As the name suggests, Chesapeake Beach is an adorable small town on the shores of Chesapeake Bay. It is a great weekend destination in the state, only an hour or so from Baltimore and Washington, DC. Upon arrival, tourists rejoice at the public boat launch, where they can participate in kayaking, canoeing, paddleboarding, and on-the-water fishing. Speaking of fishing, the town is a hub for anglers thanks to its range of fish species, such as red drum, black drum, and kingfish. Next to the harbor is Chesapeake Beach Water Park, which has activities for the whole family. Activities range from floating down the lazy river on a raft to racing down the waterslides, which offer quick glimpses of the tranquil bay.
Visitors wanting to stay on land can head to the Historic Heritage Trail, which offers walking paths leading to the railway museum and Bayfront Park. Another option nearby is the Railway Trail, which follows an old railroad line along Fishing Creek. For dinner, choose from various dishes such as fresh-caught crab, pizza, or a classic bar and grill. If this isn’t enough, continue your trip in the adjacent community of North Beach, featuring sandy beaches and rentals such as beach chairs, umbrellas, and floaties.
Stevensville, Maryland
A creative haven, Stevensville is situated on Kent Island and is connected to mainland Maryland by the William Preston Lane Jr Memorial Bay Bridge. Along with being a famous landmark, this bridge provides easy access from Annapolis and a quick connection to Baltimore. Visitors from these cities adore Stevensville’s vibrant streets, which are full of independent galleries and art stops. It is also home to an art market, making getting to know all the local vendors even easier. If anyone wants to hone their artistic ability, Creatives Corner offers classes and workshops, such as graffiti art and cheese making. Hand in hand with the vibrance, the historic downtown area also features rustic buildings, now protected and available for photos and tours. Such places include the 1800s Old Post Office, the 1902 Stevensville Train Depot, and the 1903 Stevensville Bank.
In addition to the static attractions, visitors should check out what events might occur during their visit. For example, Kent Island Day in May brings authors, artists, and vendors together. In June, join in on Paint Stevensville, where local painters show their talent. Similarly, in November, come down for the Classic Car Show. One can also take in all the sights at once by hitting the skies with Delmarva Hot Air Balloon tours for a memorable experience in Maryland.
Easily accessible by nearby cities such as Washington, DC, Baltimore, MD, and Norfolk, VA, Chesapeake Bay offers endless opportunities for waterside fun. Tourists can choose from more populated towns with all the amenities they need, like shopping malls and waterparks, or spend some time in quaint areas to de-stress and embrace history. No matter what you're looking to experience, you'll surely find the perfect getaway in this scenic abode shared by Maryland and Virginia.
