Eight Cute Towns on the Chesapeake Bay You Should See

Chesapeake Bay is the largest estuary in the United States. The lovely towns that line the coasts of six states are often a treat for people who come to visit. Chesapeake Bay is between 3.4 and 35 miles wide and has lots of things to see and do. There are now more businesses and homes in this area than there used to be, which has brought in more tourists and residents over time. Chesapeake Bay is a well-rounded place with something for everyone. It has beautiful scenery and nature. Since the estuary has a long and interesting history, many of its towns have become popular vacation spots. These Maryland and Virginia towns are the most fun and unique in the Chesapeake Bay area. They will make you want to visit again and again.

Havre de Grace, Maryland

Have de Grace is at the point where the Chesapeake Bay and the Susquehanna River meet. It has a lot to offer all kinds of visitors. The Concord Point Lighthouse and Keeper’s House Museum is a seaside attraction. It is home to the oldest lighthouse on the Chesapeake Bay that is open to the public. The town of Havre de Grace is one of 25 Arts and Entertainment Districts in Maryland. It is full of art workshops and galleries for all kinds of art lovers, like Gallery 220, Unlimited Art Studio, and more. The main streets are lined with shops, bars, antique shops, and other places where people can meet and talk to locals. During the winter, people can also enjoy Havre de Grace’s Holly Jolly Days, which are themed around Christmas.

Chestertown, Maryland

The 2020 census showed that only 5,532 people were living in Chestertown, but the town is anything but small. This Maryland town is one of a kind because it was founded in 1706. This cute town holds the “Chestertown Tea Party Festival” every year and is full of historic sites and well-kept or re-created buildings that remind us of where it came from. The estuary and the town’s maritime past can be explored in many ways. There is a recreation of the Sultana from 1768 and one of the largest Tall Ship gatherings on the East Coast.

Onancock, Virginia

With less than 1,200 people, Onancock has learned how to live up to its name as “the Gem of the Eastern Shore.” Onancock has every kind of art you can think of and has a thriving art community. This town has been around since the 1600s and is made up of artists, craftsmen, glassblowers, and more. Along with art, Onancock offers many nature and wildlife trips that teach people about the ecosystems in the area. Like most of the Chesapeake Bay, Onancock has a lot of bed and breakfasts that make guests feel at home while they’re there. If you want to learn more about how the locals live, you can go to one of their many award-winning restaurants or the International Film Festival at their old movie theater.

St. Michaels, Maryland

From the 1600s on, St. Michael has been around. In the beginning, the town was a trading place for tobacco farmers and trappers. The town is now a harbor town that connects to many big places, but it still has the magic and charm of its early days. A lot of the interesting things in St. Michael are close to each other because the town is laid out so that people can walk it. The Clark Gallery of Fine and Hopkins Original Art are two of the town’s lively art scenes. The nearby Chesapeake Bay Maritime Museum and St. Michael’s Museums are great places to learn about the past of the town. It has streets lined with Victorian-era buildings that are home to unique shops and stores that bring back some of the amazing things that were first found there in the 1600s.

Cape Charles, Virginia

One of the most coastal and fun towns in the Chesapeake Bay is in Cape Charles, a planned community built in the Victorian era. Because Cape Charles is on the Chesapeake Bay, there are many water and maritime-themed activities to enjoy, like sailing and stand-up paddleboarding. Many old towns try to add modern touches to their communities, but Cape Charles still looks like it did when it was first built in the 1880s. Along with its Victorian beauty, this town is great for movie fans because it has the Historic Palace Theatre, which was built in 1942. Cape Charles has a lot of interesting things to see and do. It has both historical and coastal beauty.

The city of Cambridge

Cambridge is another unique town that has found a balance between its past and its modern boom. It is one of the oldest colonial places in the state. People who love real building will be amazed by many of the homes in Downtown Cambridge that were built in the 1700s and 1800s. Cambridge is known for more than just its maritime past. It is also close to where Harriet Tubman was born and played a part in the Underground Railroad. There are many places in Cambridge where you can learn more about its past. The town loves telling tourists about its heroes and interesting spots.

Easton, United States

A small coastal town called Easton has grown into an arts and culture hub, with about 16,500 people living there. Easton is only 70 miles east of Washington, D.C., and there are lots of interesting things to see there. Famous coffee shops and restaurants let tourists see how people live in the area. Easton is unique because it has so many golf fields and places to shoot skeets. The evenings and nights are full of events and community days, such as art walks and shows of old cars. History buffs will enjoy the main streets that are lined with buildings from the Victorian and Colonial eras.

City of Chesapeake, Maryland

Chesapeake City, which got a new name in 1839, is one of the busiest rivers in the world. This makes it a great place to start your trip around the Chesapeake Bay. This town has homes and gardens from the 1800s that are on the National and State Historic Registries. It is a great place for tourists who want to see some of the original buildings and designs of the town. The C&D Canal Museum tells a fun and interesting story about the history of the canal and how Chesapeake City came to be. With its many bed and breakfasts, antique shops, and places to have fun, this town makes sure that guests have a great time during their whole trip. A short drive from Chesapeake City is the Turkey Point Lighthouse, which is famous in the area and can be seen by tourists. This town is a must-see for anyone interested in Chesapeake Bay history. It is a lovely place to visit with lots of fun things to do.