Best Places to Visit and Things to Do Along the Chesapeake Bay

view of Chesapeake bay

Chesapeake Bay is often considered one of the most beautiful parts of the US. All in all, the area is perfect for several different types of vacations. The area has over 20 miles of waterways and canals, and tons of hiking and biking trails for those interested in the outdoors. For those who’d rather spend their time in cities, there are also museums, restaurants, and galleries to explore. And this is all throughout several different cities and areas in the bay. So, no matter what kind of vacation you’re looking for, Chesapeake Bay is sure to have something for you. So, in order to help you plan your vacation to the Chesapeake Bay, we put together a list of the best places to visit and things to do along the Chesapeake Bay.

Sail around Annapolis

Starting off the list of places to visit and things to do along the Chesapeake Bay, a visit to the sailing capital of the world is a must. Annapolis is a beautiful city by itself, but the real draw of the city is its docks. October is when the official boat shows happen, you can expect to see all kinds of sailboat races year-round. And if you want to get in on the action, you can rent a boat tour or rent a sailboat. Either is a great option, although if you’re not familiar with boating we strongly recommend the first option. And when planning your trip, remember that there are things to do early on in the process. Preparation is key to every successful vacation, and planning should be taken seriously. So, make sure you have everything covered well ahead of time so you can enjoy the trip properly.

Adkins Arboretum Ridgely, MD

Found in Ridgely, Maryland, the Adkins Arboretum is a great place if you want to learn about nature and relax. The arboretum is a 400-acre native garden, built to preserve and protect around 600 native plant species. As the arboretum is dedicated to preserving and appreciating the native species of Chesapeake Bay, they offer educational programs, guided walks, demonstrations, and so on to visitors. So, if you’re interested in seeing some beautiful nature and learning about it, this is the place to be. Attractions like this are what convince a lot of tourists to actually settle in the Chesapeake Bay. If you find yourself tempted to move here as well, there are various options to choose from when it comes to moving. We recommend relying on local experts to get you settled in comfortably. After all, experts who know the area are the best bet in the long run.

Pay a visit to Smith Island

Continuing the list of places to visit and things to do along the Chesapeake Bay, Smith Island is another excellent location. Smith Island can be found twelve miles offshore, in the middle of Chesapeake Bay’s waters. You can get there easily via a passenger-only ferry, and experience the state’s dessert, the Smith Island Cake where it was created. Additionally, the island offers bird watching and golfing in a very scenic, relaxed, and quiet atmosphere. So, if you’re looking for a quiet and laid-back spot to add to your vacation, Smith Island is a perfect choice. However, remember that selecting accommodations ahead of time is very important. After all, staying in a bad hotel can often ruin your vacation, so deciding on one you like early is vital. Otherwise, you leave yourself open to a lot of issues with both finding and booking hotels, so do this as early as possible.

Calvert Cliffs State Park

Found in Lusby, the Calvert Cliffs State Park is a must for anyone interested in nature. This state park is focused on preserving the Calvery Cliffs, an area where people have discovered over 600 unique species of fossils. The Calvert Cliffs extend for 24 miles along the easter part of the Calver Peninsula. They used to be submerged under a shallow sea, which revealed these massive cliffs when it receded. Now, the cliffs are a treasure trove of fossils and other prehistoric items. Oysters, ancient shark teeth, and the remains of prehistoric species are all commonplace in this area. However, while you’re out exploring, remember that you shouldn’t bring everything important with you. Experts from Excalibur Moving and Storage recommend using a short-term storage unit. This is, all in all, the safest option, as you shouldn’t leave important belongings in a hotel room either, just to be safe.


If you’re at all interested in art or history, then Chestertown is a must-visit for you. Chestertown is a rather beautiful historic college town. The town’s history as the home port of the Sultana schooner is only part of its extensive history. In May, the town holds the Chestertown Tea Party Festival, during which you can see a reenactment of the 1774 incident when the residents of Chestertown dumped tea into the Chester River as a sign of solidarity for Boston. Additionally, the town is home to a thriving and unique arts community. So, make sure to spend some time exploring the town’s eccentricities. And when planning your trip, remember to pack everything you need for a comfortable trip. Forgetting certain items can make your trip a lot more uncomfortable. So, think ahead about what you need and remember to pack everything ahead of time just in case.

Best places to visit and things to do along the Chesapeake Bay – wrap up

Chesapeake Bay has a lot of wonderful things for every type of traveler in it. From exciting adventures to beautiful gardens to relax in, no matter what kind of vacation you’re looking for, you’ll find it in Chesapeake Bay. However, planning is a vital part of every successful vacation, so take your time and plan for everything. With so much to do it can be easy to get overwhelmed, so take your time and pick out the spots you’d like to visit. We hope this list of the best places to visit and things to do along the Chesapeake Bay helps you with the planning, and we wish you a great trip.

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