10 Best Chesapeake Bay Towns You Must Visit

Are you looking for the best Chesapeake Bay towns? You are in the right place.

In this article, we will walk you through towns around the Chesapeake Bay, and tell you more about this beautiful area.

The Chesapeake Bay area is a beautiful region. It is located on the East Coast of the United States, spanning parts of Maryland and Virginia. The area is named after the Chesapeake Bay, the largest estuary in the United States and home to a diverse array of wildlife and plant species.

One of the main attractions of the Chesapeake Bay area is the natural beauty of the region. The bay itself offers opportunities for boating, fishing, and other water activities. There are many parks and nature preserves in the area for hiking, camping, and wildlife watching. The region is also home to many historic sites, including colonial-era towns. There are so many Things to Do in the Chesapeake Bay Area.

You will need a car to explore this area as public transportation is limited. Parking can also be a challenge in some towns so check before you go or be prepared to walk or bike.

So are you ready for us to walk you through some of the cute towns in the Chesapeake Bay? These are just the start of the wonderful Chesapeake Bay towns to explore in this area.

10 Best Chesapeake Bay Towns You Must Visit

Chesapeake City, Maryland

Located at the northern end of the Chesapeake Bay, Chesapeake City is one of the picturesque eastern shore towns. It has a historic district featuring Victorian homes, boutique shops, and art galleries. If you are looking for small Chesapeake Bay towns this is a great place to start.

This town has one of the most picturesque waterfronts that you must visit. Biking or walking along the historic canal and visiting the Chesapeake & Delaware Canal Canal Museum is also essential. And you can also take boat tours down the canal.

The restaurants in this town are phenomenal and the seafood choices are exceptional. There is nothing like dining in one of the waterfront restaurants while watching the world go by.

This is one of the towns to visit in the Chesapeake Bay if you have a lot of different people to please. It’s one of the best small towns in Maryland.

Cape Charles, Virginia

On the Eastern Shore of Virginia, Cape Charles is known for its pristine beaches, quaint downtown area, and charming Victorian homes. This is one of the quaint Chesapeake Bay towns that has a family-friendly atmosphere.

At the southern end of the Delmarva Peninsula, this town was once the railroading hub many of its industrial past left for tourists to enjoy. One of the must-see things, while you are here, is the Cape Charles Lighthouse.

Seafood restaurants abound here and dolphin cruises and other boat trips are plenty. It’s a lovely walkable town with a beach that will keep everyone happy. It is one of the best towns on the eastern shore.

Annapolis, Maryland

Known as the “Sailing Capital of the World,” Annapolis is a historic city with a thriving downtown area filled with shops, restaurants, and historic sites. As the capital of Maryland, some may argue it isn’t one of the cute towns in the Chesapeake Bay but we just had to include it.

There is a lot to do in Annapolis, it has a historic charm and gives a glimpse into colonial America. Expect lots of boutique shops, great Annapolis restaurants, and lively nightlife.

Must-do activities include touring the United States Naval Academy and visiting the Maryland State House. Sailing out on the Chesapeake Bay is also an option.

If you are looking for that small-town experience with all the lights and action of somewhere bigger this is the place to come. It is one of the best Chesapeake Bay tourist towns.

Havre de Grace, Maryland

Situated at the top of the Chesapeake Bay, Havre de Grace is a historic town with a bustling downtown area, charming bed and breakfasts, and a picturesque waterfront.

Named after a French seaport this is one of the small towns in Chesapeake Bay which has an abundance of antique shops and restaurants and many opportunities for outdoor recreation. The town is known for its maritime history and charming downtown.

Must-do activities include visiting the Havre de Grace Decoy Museum (it’s the duck decoy capital of the world) and exploring the Susquehanna State Park which has some great hiking. A tour of the Concord Point Lighthouse, the oldest publicly accessible lighthouse, is also something that should be on your to-do list.

This is one of the small Chesapeake Bay towns that has something to please everyone whatever they like doing.

Solomons Island, Maryland

Located on the southern tip of Calvert County, Solomons Island is a charming waterfront town with a rich maritime history. This is one of the best Chesapeake Bay tourist towns if you are looking for a very peaceful atmosphere and lots to explore.

The Calvert Marine Museum is the place to go to explore the history of the town. The museums exhibit one of the few remaining “screw-pile” lighthouses on the Bay which you can visit.

Solomons Island also has a great boardwalk which is a great place for shopping, dining, and leisure.

The Annmarie Sculpture Garden is also a great place to visit. It’s a Smithsonian-affiliated establishment and mixes the great outside with world-renowned artists’ work.

This is one of the towns to visit in the Chesapeake Bay area.

Cambridge, Maryland

A historic town on Maryland’s Eastern Shore, Cambridge offers visitors the opportunity to explore colonial architecture, and outdoor adventures.

This town has a very authentic feel about it and the downtown area is full of unique one of kind stores, galleries, and wonderful restaurants.

Must-do activities include visiting the Harriet Tubman Museum and Educational Center and taking a kayak tour of the Blackwater National Wildlife Refuge. Paddleboarding the Choptank River is also great for those who want a bit more adventure.

It is also believed that Cambridge is home to the haunted street on the Eastern Shore so take a ghost tour if that is your thing.

This is one of the prettiest towns in the Chesapeake Bay that will please historians, shoppers, and adventurers alike.

Saint Michaels, Maryland

Situated on Maryland’s Eastern Shore, Saint Michaels is a popular tourist destination known for its picturesque harbor and charming Main Street. Founded in the 1600s it was a thriving seaport and it seems to have taken a lot of that personality into what remains today.

This is one of the eastern shore towns that is bustling with things to do and while it still has all the historic sites and one-off shops it isn’t quite as peaceful as some of its neighbors. It’s a perfect family destination.

Must-do activities include visiting the Chesapeake Bay Maritime Museum and taking a scenic boat tour of the harbor. You can also take a scenic bike ride on the Rails to Trails path which is close by. And of course, more adventurous sailing or kayaking is available on the bay.

This is one of the best towns on the eastern shore that makes a perfect family destination.

Chincoteague Island, Virginia

Chincoteague Island, Virginia is a hidden gem located on the Eastern Shore of Virginia, just south of the Maryland border. It’s one of the best Chesapeake Bay beach towns for those looking to experience the natural beauty of the East Coast, with plenty of opportunities for outdoor activities and relaxation.

If you love wildlife you will love this town as is home to herds of wild horses roaming the shores of the Atlantic Ocean. These ponies roam free on the nearby Assateague Island and you can take a pony tour if you wish or explore the area on a bike or foot. A visit here is one of the things to do in Maryland.

The beaches here are uncrowded and pristine and the Assateague Island National Seashore is a short drive away. If you love swimming and beachcombing these beaches are perfect.

One of the prettiest towns in the Chesapeake Bay it is very charming and has that real small-town atmosphere. The downtown area has enough to keep you busy but don’t expect the nightlife of some of the other towns.

Yorktown, Virginia

Yorktown, Virginia is one of the historic and charming towns around the Chesapeake Bay, located on the banks of the York River. It is a great location for history buffs, outdoor enthusiasts, and anyone looking for a relaxing getaway.

This town has a rich history, in town played a pivotal role in the American Revolution. You can explore the town’s history at the Yorktown Battlefield and the American Revolution Museum. The town also has several historic sites, including Colonial Williamsburg and Jamestown Settlement.

The downtown area is charming with plenty to do and the waterfront has beautiful views and is a great place to spend some time. Yorktown is also home to several parks and nature preserves, perfect for hiking, biking, and searching for local wildlife.

This is one of the quaint Chesapeake Bay towns that is less visited than some of the other destinations so you might not find as many restaurants and nightlife activities. It’s the place to come if you are after somewhere a little more relaxing.

Yorktown is a beautiful and historic destination that offers a chance to explore the history of the American Revolution and enjoy the natural beauty of the York River. With plenty of outdoor activities and a charming downtown area, it’s one of the small towns in  Chesapeake Bay perfect for those looking for a relaxing and educational vacation.

Easton, Maryland

Located on Maryland’s Eastern Shore this is one of the Chesapeake Bay tourist towns that has plenty of history and culture. It’s a great place to visit if you wnat a little bit of everything.

The town has many historic homes and buildings and is home to several museums and galleries, including the Academy Art Museum and the Waterfowl Festival Art Center, offering a chance to explore local art and culture.

To learn about the town’s history head to the Historical Society of Talbot County and the Easton Point Marina. The downtown area is charming as you would expect and is full of shops, restaurants, and, galleries

Easton is known for its seafood so make sure you sample the local oysters and crabs. it is located near several other charming towns, including St. Michaels and Oxford, offering a chance to explore more of the Eastern Shore.

It’s one of the best Chesapeake Bay beach towns for a relaxing vacation that offers you a chance to explore local history, culture, and nature.

The Chesapeake Bay area is a beautiful and historic region with many charming towns to explore. Whether you’re interested in colonial history, water activities, or just relaxing on the beach, there is something for everyone.

So pack your bags and get ready to explore these Chesapeake Bay towns. We hope you have an amazing vacation and come back and tell us all about it.