8 Whimsical Towns to Visit on the Chesapeake Bay
Visitors of the United States’ largest estuary, Chesapeake Bay, are often treated to the charming towns that line the coasts of six states. Ranging 3.4 to 35 miles wide, Chesapeake Bay has plenty to do and see. Over the years, this area has seen an emergence in its commercial and residential centers, which has led to more visitors and residents over time. Coupled with beautiful landscapes and nature, Chesapeake Bay is a well-rounded area with something for all. Thanks to the area’s rich and lengthy past and location, many of the estuary’s towns have become tourist spots of their own. These towns in Maryland and Virginia represent the best of Chesapeake’s whimsical towns that capture the area’s essence and keep you coming back for more.
Havre de Grace, Maryland
Located at the intersection of the Chesapeake Bay and Susquehanna River, Have de Grace has something for every type of visitor. Seaside points of interest include the Concord Point Lighthouse and Keeper’s House Museum, which is home to the oldest publicly accessible lighthouse on the Chesapeake Bay. Also home to one of 25 designated Arts and Entertainment Districts in Maryland, Havre de Grace is filled with art studios and galleries for every type of art lover, such as Gallery 220, Unlimited Art Studio, and more. Boutiques, antique shops, renowned restaurants, and more line up the main streets, allowing visitors to interact and get to know locals. In the winter, visitors will also get the chance to explore Havre de Grace’s Holly Jolly Days to get into the Christmas spirit.
Chestertown, Maryland
Although the 2020 census revealed a mere 5,532 population, there’s nothing small about Chestertown. Founded in 1706, this Maryland town is a unique location. Home to the annual “Chestertown Tea Party Festival”, this quaint town is filled with historic references and well-kept or recreated buildings that serve as a reminder of its origins. With a recreation of the 1768 Sultana and one of the largest Tall Ship gatherings on the East Coast, there are plenty of chances to explore the estuary and the town’s nautical history.
Onancock, Virginia
With a population under 1,200, Onancock has learned how to live up to its moniker of “the Gem of the Eastern Shore.” Hosting a vibrant art community, Onancock is home to every type of art one could imagine. Artisans, craftsmen, glassblowers, and more make up this community that dates back to the 1600s. Along with art, Onancock allows visitors to learn about the area’s ecosystems via their numerous nature and wildlife tours. As with most of the Chesapeake Bay, Onancock also boosts numerous bed and breakfasts, giving visitors a cozy and familiar feel during their stay. Those looking to know more about how the locals live can visit their numerous award-winning restaurants or the town’s International Film Festival at their old-time movie theater.
St. Michaels, Maryland
St. Michael’s past goes back to the 1600s when the town first served as a trading post for tobacco farmers and trappers. Nowadays, the town is a harbor town that serves as access to many metropolitan cities but still has the charm and wonder of its origins. Because of St. Michael’s pedestrian-friendly layout, many of the town’s points of interest are within a short walking distance of each other. The town’s vibrant art scene includes the Clark Gallery of Fine and Hopkins Original Art. Nearby, the Chesapeake Bay Maritime Museum and St. Michael’s Museums offer a charming view into the town’s history. Streets lined with Victorian-aged buildings house one-of-a-kind boutiques and retail shops that bring back some of the wonders first found in the 1600s.
Cape Charles, Virginia
The Victorian-era planned community of Cape Charles is home to one of Chesapeake Bay’s most coastal and whimsical towns. Cape Charles’ location on the shores of Chesapeake Bay allows for plenty of aquatic and maritime-inspired activities such as kayaking and stand-up paddleboarding. While many old towns will try to infuse modern details into their communities, Cape Charles appears similar to its establishment in the 1880s. Along with its Victorian charm, this town is perfect for cinephiles with the Historic Palace Theatre, built in 1942. A mixture of history and coastal charm, there’s no shortage of captivating attractions in Cape Charles.
Cambridge, Maryland
As one of the oldest colonial cities in the state, Cambridge is another offbeat town that has managed to find the balance between its past and modern boom. Fans of authentic architecture will have the chance to marvel at many of Downtown Cambridge’s homes that date back to the 1700s and 1800s. Besides its rich maritime history, Cambridge is known for its proximity to Harriet Tubman’s birthplace and its role in the Underground Railroad. Filled with plenty of places to learn more about Cambridge’s history, this town relishes teaching visitors about its heroes and one-of-a-kind locations.
Easton, Maryland
Housing approximately 16,500 residents, Easton is a small coastal town that has transformed into an arts and cultural center. While only 70 miles east of Washington D.C., Easton has plenty of places to explore for visitors. Renowned coffee shops and restaurants give visitors a glimpse into the local life. Unique to Easton are the town’s many golf courses and skeet shooting opportunities. Numerous festivals and community days fill the evenings and nights, including antique car shows and art walks. History buffs will enjoy the lined main streets with Victorian and Colonial-aged architecture.
Chesapeake City, Maryland
Renamed in 1839, Chesapeake City is among the busiest canals in the world, making it a prime spot to explore all the Chesapeake Bay offers. With homes and gardens that date back to the 1800s and on the National and State Historic Registries, this town is the perfect place for visitors who wish to explore some of the town’s original architecture and design. The C&D Canal Museum offers a fun and detailed past of the canal and gives an idea as to how Chesapeake City came about, Renowned for its bed and breakfast inns, antique shops, and entertainment spaces, this town ensures visitors are well entertained by their entire trip. Famous to the area, visitors will also have the opportunity to visit the Turkey Point Lighthouse, located a short drive from Chesapeake City. A delightful town with plenty of enrichment activities, this town is the must-see for those looking to brush up on the history of Chesapeake Bay.
Chesapeake Bay’s Hidden Gems Await
The Chesapeake Bay is home to a variety of charming small towns, each offering a unique blend of history, culture, and scenic beauty. From Havre de Grace’s historic lighthouse to the artistic heart of Onancock, these towns invite visitors to explore coastal landmarks, vibrant arts scenes, and captivating history. Whether you're strolling through Victorian-era streets or embarking on a maritime adventure, these whimsical destinations in Maryland and Virginia make for unforgettable experiences. Discover the magic of Chesapeake Bay, and allow their rich stories and welcoming communities keep you coming back for more.
