10 Unforgettable Small Towns to Visit on the Chesapeake Bay
The towns in Chesapeake Bay are unforgettable, have majestic landscapes, and offer diverse water activities for visitors. If you are looking for waterfront towns in Virginia and Maryland to explore and make memories, places like Kilmarnock, White Stone, Colonial Beach, and many more in the region are your go-to destinations. Some of the towns also have deep, rich histories tied to them, like the history of the Harriet Tubman Underground Railroad, which you will learn about when you visit Cambridge in Maryland.
Come ready for an adventure in the "Mother of Waters," and prepare to go home with plenty of keepsakes and collectibles.
Kilmarnock, Virginia
During the mid-1600s, when the town of Kilmarnock was first settled, it was called “The Crossroads.” In the early 1700s, a storehouse opened in the town, and then the owner, Steptoe, named the town after his name and store and called it Steptoe’s Ordinary. In the mid-1700s, agent Robert Gilmour changed the town’s name to Kilmarnock after Kilmarnock in Scotland. The name of the town eventually became incorporated in 1930.
The community spirit in Kilmarnock is what sets it apart. The residents are warm and welcoming. The friendly atmosphere in the town creates memorable experiences for every visitor. Relate with tourists and residents at the cool Kilmarnock Town Centre Park. Participate in events or outdoor games, or just relax and enjoy the ambiance. Glimpse the history of the town at Kilmarnock Museum, situated in one of the community’s oldest buildings. Sip or buy varieties of wine at Good Luck Cellars. Shop souvenirs at the Antique Gallery.
Tappahannock, Virginia
Tappahannock is a beautiful town on the Rappahannock River, which is the largest tributary of Chesapeake Bay. It is also the oldest town and county seat of Essex County. The name of the town means where the tide rises and falls.
This waterfront destination is a must-see town with many activities to add to your itinerary. Situated on Prince Street is the National Historic DAW Theater. It is a not-for-profit organization with amazing performances and art events. Shop vintage and collectibles from Acme Antiques, the biggest antique store in town. The best activities at Tappahannock are the watersports. Go boat cruising, touring, and fishing with Tip Sea Charters. Learn new historical facts at Essex County Museum. The Farmer’s Market will allow you to mingle with locals and buy fresh food. There is a refreshing pool at Marsh Street Park & Pool, where you will also get to relax in the park.
Irvington, Virginia
The town of Irvington used to be called Carter’s Creek because it is situated on Carter’s Creek, a side stream of the Rappahannock River. However, the town voted for the name “Irvington” in 1891. The town has grown tremendously since then and has now been appointed a historic district. From 1889 to 1907, Irvington was home to the first Chesapeake Academy.
Unwind in Compass Entertainment Complex with family-friendly games, movies, and dining. Watch exhibits or buy art at the Objects, Art, and More showcase. You will also get a beautiful seaside view while you are there. Golden Eagle Golf Club is a stunning golf course with a view of a 50-acre lake. Stop by for the view or go golfing.
Colonial Beach, Virginia
The rich history of Colonial Beach started around 500 BCE when the Native Americans were said to have lived there. The town was incorporated in 1892, and beautiful cottages and buildings were erected. One of them is the Bell House Inn, made for Alexander Graham Bell, which, unfortunately, has been closed down. However, when you visit, you can see the tall structure standing out on Irving Ave.
Get ready for a great time at Bayside Marina on Monroe Bay, where you get to explore eats or order seafood at Dockside Restaurant & Tiki Bar. Rent a fishing kit and fish at the Municipal Pier. Don’t miss out on the commercial tales of the town in the Museum at Colonial Beach.
White Stone, Virginia
White Stone is the town where the past and present meet. While the town has progressed greatly since it was founded in 1715, the intricate history of the town makes it stand out even more.
Get to know the town's history from locals at the infamous White Stone Beach, an ideal picnic and getaway destination. If you are looking to take some furniture home, check out Antique Outfitters. Watch performances and pick your favorite artists at Allure Art Center. Don’t miss the enrapturing sunset view of the river at the Windmill Point Marina.
Chestertown, Maryland
Chestertown, named after Chester River (a major tributary of Chesapeake Bay), was founded in 1706 and incorporated in 1805. It used to be the second-best port in Maryland from 1750 to 1775. The town also built beautifully designed homes around that time, just like Annapolis did.
Discover the historical treasures of Chestertown at the Historical Society of Kent County. The community people come together at the Garfield Center for the Arts to celebrate artists and watch performances; don’t miss a great time at the Prince Theater. Looking to engage in water activities, the Chestertown Marina provides boat rides and dockage services. The Kitchen at The Imperial is very keen on making customers their friends. If you love an opportunity to make friends with strangers, check them out before leaving town. Reserve a table at Casa Carmen Wines for old-style tasty wines.
Chesapeake City, Maryland
Chesapeake City is a picturesque place on a commercial canal and the only town in Maryland on a canal. Think of old homes and architectural designs; you will find them here. In today’s era, these homes still exist as museums, inns, and dine-ins. The people of this city encourage tourists to learn about the town’s history with canals at the C & D Canal Museum. Chesapeake City Museum also has more tales to offer visitors.
One of the major attractions of the city is the Chesapeake City Bridge. Take a walk on the sidewalk of the arch bridge while enjoying the ambiance of the river below. Check out the Nationally Registered South Chesapeake City Historic District. Complete your unforgettable adventure at Pell Gardens Park.
Cambridge, Maryland
Cambridge used to be known as the hub for slave trading activities. The Harriet Tubman Museum and Educational Center provides more information. The Harriet Tubman mural can also be found on an extended wall of the Educational Center. Check out Harriet Tubman Underground Railroad Park to see Harriet’s activism brought to life. The town is also a river town with lots of fishing, watersports, and boat-building activities. Be a part of this fun by cruising on the Nathan of Dorchester boat.
There is a small museum at the Choptank River Lighthouse. Learn the lighthouse's history and how it used to be near Oxford, Maryland. The town's legacy lives on at Richardson Maritime Museum, where 300-year-old boats can be found. Visit one of the oldest schools in Maryland turn museum, Stanley Institute Museum, to complete your educational tour of the town.
Havre de Grace, Maryland
Havre de Grace, meaning “Harbor of Grace,” is derived from French and was named for Le Havre, a port city in France. General Lafayette visited the town during the Revolutionary War and spoke about how the town reminded him of the French Port. This led to the change of the town's name from Harmer's Town.
Prepare to see lots of historic homes and museums in Havre de Grace, such as the Havre de Grace Decoy Museum, where adorable artworks are showcased. Learn about the commercial lifestyle of the town’s people at The Havre de Grace Maritime Museum. Friends-Concord Point Lighthouse overlooks Susquehanna River and Chesapeake Bay. Take your camera with you to capture the evening beauty of the scenery. Learn about the town’s connection with rivers and canals at Lock House Museum. Relax, go picnicking, or watch other people have fun at Millard Tydings Memorial Park.
North Beach, Maryland
The pleasant town of North Beach is known as the treasure of Chesapeake Bay. This town offers calm and relaxation to residents and tourists. At North Beach, you can walk along the North Beach Boardwalk/Beach. Watch the sunset, ride a bike, or go fishing. Another cool place to relax is the Sunrise Garden. It extends to the beach and offers a peaceful atmosphere to visitors.
The people have a vibrant history rooted in culture. Get to know all about it at Bayside History Museum. Explore the resorts, pool, and private beach at Herrington Harbour South. Get a fishing pass at the welcome center at North Beach Pier, or take a walk around the Pier. Check out Wetlands Overlook Park to observe the wildlife in the area. The town has a wheelchair-accessible area at Chesapeake Beach Railway Trail, seven minutes from North Beach, where everyone can go hiking and have a swell time.
You will surely make unforgettable memories when you go to any of these ten small towns in the Chesapeake Bay. Broaden your knowledge of American history by checking out these historical maritime towns, eating delicious seafood, and bringing home antiques.
