Annapolis, Maryland, USA downtown view over Main Street with the State House at dawn.

10 Adorable Small Towns In Chesapeake Bay

With its breathtaking beauty and iconic presence, the Chesapeake Bay is one of the most alluring destinations in the United States. Rich in history and enveloped by stunning scenery, the Bay's shoreline is dotted with charming towns and villages, each offering a unique blend of exploration opportunities. Whether you're drawn to delve into historical museums, savor local culinary delights, or embark on outdoor adventures, the Chesapeake Bay region promises diverse experiences that captivate the senses and ignite the imagination.

3-Day WeekendsTake a look at these eight ideal destinations for a long weekend along the Chesapeake Bay

Annapolis, Maryland

Annapolis, MD, USA 05-02-2021: Street view of Annapolis, Maryland with people walking in historic town and people dining outdoor sitting on tables put on street by local restaurants.
Annapolis, MD, USA 05-02-2021: Street view of Annapolis, Maryland, with people walking in the historic town and people dining outdoors. Editorial Credit: grandbrothers via Shutterstock.

Located on the banks of the Chesapeake Bay, Annapolis, Maryland, is a beloved destination for travelers from all over the world. This bustling small town offers plenty to do no matter what your interests may be. Spend an afternoon exploring historic areas such as City Dock, where visitors can relax and enjoy the water or explore the dock’s shops and art galleries. When it comes to outdoor activities, Annapolis provides visitors with plenty of opportunities for adventure. Whether you are looking for swimming spots at Sandy Point State Park or kayaking through Weems Creek, there is something here for everyone. Those who prefer hiking and biking will be happy to visit Quiet Waters Park, a 340-acre park featuring trails, playgrounds, and picnic areas.

St. Michaels, Maryland

St. Michaels, MD, USA - March 30, 2013: Some of the shops and stores in St Michaels, MD along the town's main street.
St. Michaels, MD, USA - March 30, 2013: Some of the shops and stores in St Michaels, MD, along the town's main street. Editorial Credit: George Sheldon via Shutterstock.

St. Michaels, Maryland, is a picturesque small town on the Chesapeake Bay's Eastern Shore. Attracting visitors with its old-world charm and rich history, St. Michaels is an ideal destination for anyone looking to learn and explore. Discover a handful of local museums, including the St. Michaels Museum, which offers a variety of walking tours and historical collections. Another museum worth visiting in town is the Chesapeake Bay Maritime Museum, where visitors can explore a 19th-century lighthouse and get a glimpse into life before modern times. This charming town also offers plenty of outdoor activities, including hiking along the St. Michaels Nature Trail or admiring the historic cannons and harbor views at Muskrat Park.

Cape Charles, Virginia

Cape Charles Virginia - April 23 2022: Aerial View of Mason Ave in Cape Charles with businesses looking east.
Cape Charles, Virginia - April 23, 2022: Aerial View of Mason Ave in Cape Charles with businesses looking east. Editorial Credit: Kyle J Little via Shutterstock.

Despite its small size, Cape Charles, Virginia, offers plenty of opportunities for tourists looking for culture and recreational activities. From its long stretches of sandy beaches to the beautiful Victorian-era buildings in the historic district–there is no shortage of things to see and do here. Those who taste wanderlust should visit the Cape Charles Natural Area Preserve, which features a long boardwalk, rare woodlands, and bluffs overlooking the Chesapeake Bay. Dive into the town’s history at the Cape Charles Museum. Then, finish the day with some drinks at Cape Charles Brewing Company or indulge in tasty southern-style seafood plates at The Shanty.

Kent Island, Maryland

Kent Island, Queen Anne's County, Maryland, USA, Biking the Cross Island Trail, May 4, 2004.
Kent Island, Queen Anne's County, Maryland, USA, Biking the Cross Island Trail, May 4, 2004. Editorial Credit: Malachi Jacobs via Shutterstock.

Kent Island, Maryland, is the largest island in the Chesapeake Bay and one of the most popular tourist destinations. In addition to the beautiful landscape, Kent Island also offers a wide range of activities for outdoor enthusiasts. Take a stroll on the iconic Cross Island Trail, which passes through farmlands, wooded areas, and calming meadows. Hikers and bikers will also find charming footbridges and wetlands along the way. Another must-see spot is the award-winning Terrapin Nature Park. Here, visitors can explore hiking trails and relax on the sandy beach. Regarding attractions, visitors can take advantage of various cultural activities, including visiting the Stevensville Historic District and stopping for a bite to eat at Big Bats Cafe.

Urbanna, Virginia

Urbanna Creek, Urbanna Virginia. By C Watts - Urbanna Creek, Urbanna Virginia, CC BY 2.0, https://commons.wikimedia.org/w/index.php?curid=63577448
Urbanna Creek, Urbanna Virginia. By C Watts - Urbanna Creek, Urbanna Virginia, CC BY 2.0, https://commons.wikimedia.org/w/index.php?curid=63577448

Located on the shores of the Rappahannock River, Urbanna, Virginia, is a charming little enclave known for its unique blend of historical sites, recreational activities, and coastal beauty. Get a taste of the town’s rich history at the Urbanna Museum and Visitor Center, or take yourself on the Museum in the Street Walking Tour. Those looking to shop will find plenty to explore here as well. From strolling through the Urbanna Flea Market and antique shop to exploring the Urbana Town Marina, there is something for everyone. Outdoor activities are plentiful, too; enjoy picnics and river views at Waterman’s Park and Taber Park, or hop aboard The Pearl, a local trolly ride. Visitors can also participate in various events throughout the year, such as the annual Urbanna Oyster Festival, which brings together locals and tourists for good food and good fun.

Onancock, Virginia

Onancock VA, USA — November 15, 2022: Red brick early 20th century store front on Market street housing the Red Queen Gallery in early evening light. Featuring works of art. Red bench on sidewalk.
Onancock, VA, USA — November 15, 2022: Red brick early 20th-century storefront on Market Street housing the Red Queen Gallery in the early evening light. Featuring works of art. Red bench on the sidewalk. Editorial Credit: John Blottman via Shutterstock.

Filled with cultural highlights, entertainment, and delicious places to eat, it’s not hard to spend the day in Onancock, Virginia. Discover a range of artifacts celebrating maritime history at Watermen's Heritage Foundation or explore Ker Place, a historic house displaying a range of period art and furnishings. This easily walkable town also features a wharf with pretty water views, plenty of 19th-century homes, and various art galleries and theatres to entertain visitors. Get a hearty serving of seafood at Mallards At The Wharf, a local restaurant with historical roots and waterfront views. And don’t forget to take a ride on the  Tangier Island Ferry, which travels from Onancock to a truly unique island on the Chesapeake Bay.

Solomons Island, Maryland

Solomons Island, Maryland.
Solomons Island, Maryland.

Those looking for a relaxing day filled with nature, wining, and dining will be pleased with what Solomons Island offers, a charming little town tucked away on the banks of the Patuxent River in Calvert County. Pay a visit to the Drum Point Lighthouse at the Calvert Marine Museum, where curious visitors can read lighthouse log entries dating back to 1883. While there, don’t forget to explore the rest of the museum, which offers a unique look at the history of the Chesapeake Bay, a charming marsh boardwalk, and various engaging educational opportunities. To taste the outdoors, take a drive to the nearby Calvert Cliffs State Park – here, travelers can uncover unique fossils and enjoy the sandy beach. When meal time rolls around, there will be a range of choices from the Lighthouse Restaurant and Dockbar to the Tiki Bar & Grill Solomons and a handful of others.

Easton, Maryland

EASTON, MARYLAND - CIRCA 1990's: Main Street, Easton, Maryland.
EASTON, MARYLAND - CIRCA 1990's: Main Street, Easton, Maryland. Editorial Credit: Joseph Sohm via Shutterstock.

Located in the heart of Talbot County on Maryland's Eastern Shore, Easton is a popular destination for visitors far and wide. Immerse yourself in the town's past on a Historic Easton Walking Tour, which provides visitors with an in-depth look at the history and culture of this charming small town. Or, spend an afternoon browsing fresh produce, furniture, and gifts at the Easton Amish Market. The Easton Point Marina is an ideal stop for boaters exploring the region by water. The marina also offers various amenities, including docking spaces, fuel services, restrooms, and several nearby restaurants where foodies can take advantage of tasty local cuisine. Vino lovers will want to explore the Far Eastern Shore Winery, which is one stop along the famous Chesapeake Wine Trail.

Chincoteague, Virginia

Chincoteague. Virginia. USA. August 15, 2020 Wooden pier and hotels next to the pier. Summer, Travel, Vacation and Holiday concept.

Chincoteague, Virginia, USA, August 15, 2020, Wooden pier and hotels next to the pier. Editorial Credit: Kosoff Via Shutterstock.

Known for its wild ponies and beautiful beaches, the picturesque island community of Chincoteague, Virginia, has long been a popular destination for visitors looking to escape the hustle and bustle of everyday life. Those looking to get a memorable view of the local wildlife should book a Saltwater Pony Tour. This scenic cruise lets visitors see wild ponies, bald eagles, and dolphins. The Chincoteague National Wildlife Refuge is another beloved natural area featuring wildlife, dunes, and sandy shores.

Cambridge, Maryland

Choptank River Lighthouse, Cambridge, MD.
Choptank River Lighthouse, Cambridge, MD.

Located along the beautiful Choptank River, Cambridge, Maryland, offers visitors a peaceful atmosphere and many things to explore. From outdoor activities such as canoeing down the Choptank River or visiting Great Marsh Park to unique events at the Dorchester Arts Center–there’s something for everyone in this charming town. Cycling is a great way to explore the Eastern Shore of Cambridge. With its flat terrain and scenic views, this area provides cyclists with a challenging yet enjoyable ride. There are plenty of biking trails in and around Cambridge that vary in difficulty level so that everyone can find something suitable to their skill level. 

Embracing the Charm of Chesapeake Bay

The small towns and villages nestled around the Chesapeake Bay region offer an enchanting gateway to discover the area's distinct culture, natural beauty, and rich history. From exhilarating island ferry rides to wildlife encounters like tours filled with wild ponies, the charm of this region unfolds in endless ways. Whether you're a history buff, nature lover, or seek serenity, exploring these Chesapeake Bay communities will leave you with greater insights and cherished memories. Delight in the authenticity, be inspired by the landscapes and let the Chesapeake Bay be your next unforgettable adventure.

A Taste of History, Culture, Cuisine, and Natural BeautyThese small towns in the Chesapeake Bay come alive in summer.
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Amber Van Wort August 1 2023 in Places

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