8 Best Chesapeake Bay Things to Do for a Great Vacation

You’re about to discover the best Chesapeake Bay things to do that will make for a great coastal vacation.

Whether you’re yearning for a relaxing retreat away, dream of seeing the wild ponies of Chincoteague Island, or crave boating adventures, Chesapeake Bay has it all on offer.

You’ll even learn about beautiful beach spots and explore highlights of an excellent wine trail.

These attractions near Chesapeake Bay provide the perfect blend of sun, fun, and serenity.

So, let’s look closer at these great things to do near Chesapeake Bay, below. Then, you can look forward to experiencing them for yourself when you visit.

CONTENTS — In this article, you will discover the 8 best Chesapeake Bay things to do, including:

• Explore the Chesapeake Bay Region
• Annapolis
• Chesapeake City
• Adkins Arboretum
• Sandy Point State Park
• Chesapeake Wine Trail
• Chincoteague Island
• Caledon State Park
• Cape Charles
• Final Thoughts on Chesapeake Bay Things to Do
• Next Steps

8 Best Places to Visit Near Chesapeake Bay

Imagine yourself standing on the serene shores of the Chesapeake Bay, with the gentle breeze caressing your face and the rhythmic sound of the waves lulling you into tranquility while on your trip to Chesapeake Bay.

Now, picture the adventure that awaits just beyond this picturesque scene.

Nestled in the heart of the East Coast, the Chesapeake Bay region offers many captivating destinations that await you. From historic towns to breathtaking natural wonders, you’ll find amazing places to explore near the Chesapeake Bay.

Whether you crave the charm of Annapolis, the allure of Chincoteague Island, or the beauty of Caledon State Park, each of these eight destinations has something unique.

So pack your bags, grab a map, and embark on an unforgettable journey through eight of the best Chesapeake Bay things to do.

1. Annapolis [Maryland]

If you’re looking for a charming coastal city with a rich nautical history, Annapolis is the place for you.

This vibrant and contemporary city, known as a “Museum without Walls,” offers a perfect blend of modern living and architectural history.

Annapolis is deeply connected to its nautical heritage and the Chesapeake Bay, with waterways leading the way.

Sailing and boating are extremely popular in Annapolis, which hosts several local boat shows every year. In fact, it’s one of the best Chesapeake Bay things to do.

And while Annapolis is renowned for its sailing allure, the surrounding countryside is equally enchanting. Miles of Chesapeake Bay shoreline offers a mesmerizing dance to the rhythm of the tides. The picturesque nautical villages are truly a sight to behold.

One must-visit destination is Historic London Town and Gardens. This former colonial port city has been transformed into an interpretive village with a native garden along the South River.

2. Chesapeake City [Maryland]

Located along the C&D Canal in eastern Maryland, you’ll find Chesapeake City. This charming waterfront town offers a delightful getaway, with its historic downtown area and enjoyable activities.

It’s the perfect destination for a day trip or a peaceful weekend escape.

One of the highlights of visiting picturesque Chesapeake City is its location along the Chesapeake & Delaware Canal. Here, you can select from a range of opportunities to enjoy the water at Chesapeake Bay.

Several marinas in town provide docking options for boat owners, while various companies offer cruises. Either way, you can thoroughly enjoy your time on the water.

Cruise options include sightseeing tours, sunset cruises, and mimosa brunch cruises. It’s a wonderful way to experience the town’s waterside charm and enjoy the beautiful views!

3. Adkins Arboretum [Ridgely, Maryland]

When you venture to Adkins Arboretum, you’ll discover a breathtaking 400-acre botanical haven dedicated to conserving and promoting the unique flora of the Mid-Atlantic Coastal Plain.

This remarkable institution is a significant natural, educational, and cultural resource.

The arboretum’s collection showcases native plant communities cultivated in gardens and arranged in various natural patterns.

You’ll behold beautiful:

• Meadows
• Old fields
• Pine plantations
• Young hardwood forests
• Mature bottomland forests
• Wetlands

Open daily from sunrise to sunset, the Arboretum’s grounds offer nature enthusiasts a serene and captivating experience.

As you explore the diverse landscapes, you’ll witness the beauty of indigenous plant species. These play vital roles in providing wildlife habitats and essential ecosystem processes, such as air and water purification.

4. Sandy Point State Park [Annapolis, Maryland]

With its serene atmosphere and wide range of activities, Sandy Point State Park is the perfect nature retreat for outdoor enthusiasts visiting the East Coast.

Imagine spending a sunny day swimming in the crystal-clear waters of Chesapeake Bay, followed by a relaxing picnic on the park’s picturesque beach.

Located just outside Annapolis, Maryland, this 786-acre park offers a tranquil escape from the hustle and bustle of urban life.

Despite its proximity to major cities like Washington, D.C., and Baltimore, Sandy Point State Park feels like a world away.

There is something for everyone to enjoy at Sandy Point State Park. From swimming, fishing, and crabbing to boating and hiking, outdoor enthusiasts will find endless opportunities for adventure.

The park provides you with essential amenities to make the best of your visit, including:

• Picnic areas
• Shelters
• Showers
• Restrooms
• A food concession stand

Families especially love the park’s beach, which is patrolled by lifeguards from Memorial Day to Labor Day, ensuring a safe environment for swimmers.

5. Chesapeake Wine Trail

Immerse yourself in the vibrant flavors of Maryland’s Atlantic Coastal Plain region as you embark on a journey along the Chesapeake Wine Trail.

There, the finest wines await!

This unique experience blends the warm and inviting ambiance of the Eastern Shore with wines that perfectly complement Maryland’s exceptional seafood offerings.

Along the Chesapeake Wine Trail, you will discover a treasure trove of wineries showcasing the best of what Maryland has to offer. Here are three must-visit wineries along the trail:

• Crow Vineyard & Winery: Nestled in the heart of Maryland’s Eastern Shore, Crow Vineyard & Winery is known for its sustainable farming practices and award-winning wines. Enjoy a tasting of their handcrafted wines, including their signature Barbera, as you take in the breathtaking views of the vineyard.
• Layton’s Chance Vineyard & Winery: This family-owned winery is a hidden gem on the Chesapeake Wine Trail. Experience the laid-back atmosphere as you sample their diverse selection of wines, from crisp whites to bold reds. Don’t miss their popular Chardonnay or their unique Spiced Wassail Wine.
• St. Michaels Winery: Located in the charming town of St. Michaels, this winery offers a delightful tasting experience. Sip on their award-winning wines, such as their Cabernet Franc or their popular Chesapeake White, while enjoying the picturesque views of the Chesapeake Bay.

When you embark on the Chesapeake Wine Trail, let your taste buds savor the rich flavors of Maryland’s finest wines, all while soaking in the beauty and charm of the Eastern Shore.

It’s truly one of the best Chesapeake Bay things to do, especially if you love wine and beautiful vineyards. This is an experience that will leave you wanting more.

6. Chincoteague Island [Virginia]

Hidden amidst the ethereal beauty of Virginia’s Eastern Shore, Chincoteague Island beckons visitors with its enchanting landscapes and captivating wildlife.

As you step onto this serene retreat, you’ll be greeted by a sense of tranquility that can only be found in a place untouched by the hustle and bustle of big cities.

Chincoteague Island, made famous by the 1947 novel Misty of Chincoteague by Marguerite Henry, offers a peaceful escape from the crowded beaches and busy streets.

Here, you won’t find towering high rises or crowded boardwalks. Instead, you’ll discover a relaxed atmosphere that lets you truly unwind and connect with nature.

The island is the gateway to the Virginia portion of Assateague Island and the Chincoteague National Wildlife Refuge. That’s where you can witness the famous Chincoteague Wild Ponies in their natural habitat!

From leisurely beach days to breathtaking sunsets over Chincoteague Bay, this island paradise provides endless opportunities for enjoyment.

Explore the untouched beauty of nature on Chincoteague Island. You can stroll along pristine beaches, go kayaking in the calm waters, or embark on a wildlife tour to spot ospreys, herons, and other magnificent creatures.

This is one of the Chesapeake Bay things to do you won’t want to miss!

7. Caledon State Park [King George, Virginia]

Located in King George County, Caledon State Park offers visitors a chance to explore old-growth forests, witness bald eagles in their natural habitat, and learn about the park’s rich history through its Smoot House and Visitor Center.

Nestled amidst the serene beauty of the park, you can immerse yourself in the tranquil ambiance of the old-growth forests.

The towering trees provide a canopy of shade, creating the perfect setting for a peaceful hike or a stroll. And the crisp scent of pine fills the air, transporting you to a world untouched by time.

As you venture through the trails, keep your eyes peeled for the majestic bald eagles soaring gracefully above.

These magnificent creatures have made Caledon State Park their sanctuary.

When you witness them in their protected natural habitat, it is truly awe-inspiring! The sight of their wings spread wide against the expansive sky is a sight that will leave you breathless. Seeing these amazing creatures is one of the Chesapeake Bays things to do that is like no other.

You’ll experience the wonder and connection with nature as you explore the diverse wildlife that calls Caledon State Park home.

From the playful squirrels scurrying along the forest floor to the elusive deer gracefully grazing in the meadows, every encounter with the park’s inhabitants is a reminder of the delicate balance of nature.

8. Cape Charles [Northampton County, Virginia]

Situated on a small peninsula, Cape Charles offers a vibrant and diverse experience for all who visit.

As you stroll through the town’s bustling commercial center, you’ll find an array of shops, restaurants, and antique stores to satisfy your every need.

Or, immerse yourself in the rich history of Cape Charles by visiting its museums and historic buildings.

If you’re a nature enthusiasts, you’ll be delighted by the range of outdoor activities you can choose from, like the:

• Public beach
• Golf courses
• Harbor
• Marinas
• Boat ramp (perfect for enjoying water activities and sport fishing!)

If you want a relaxing day by the water, head to Cape Charles Town Beach. You’ll find easy access at the end of every block and no entrance or parking fees. This makes it the perfect spot to soak up the sun and enjoy the beautiful surroundings.

Adjacent to the beach, you’ll find the Cape Charles Fishing Pier and LOVEwork, a local art installation, adding even more charm to your visit.

Finally, don’t miss the opportunity to explore Central Park in the heart of historic downtown Cape Charles.

With its pergola, gazebo, benches, and beautiful fountain, it’s the ideal place for you to relax and take in the town’s enchanting atmosphere.

Final Thoughts on Chesapeake Bay Things to Do

So, there you have it—the eight best places to visit near the Chesapeake Bay.

From the historic charm of Annapolis to the natural beauty of Caledon State Park, there’s something for everyone to enjoy.

Whether you’re a wine lover, a beachgoer, or a nature enthusiast, these destinations have got you covered. They are truly some of the best Chesapeake Bay things to do.

So pack your bags, grab your camera, and get ready for an adventure you won’t soon forget.

Happy travels!

Next Steps

For more about visiting Maryland and Virginia while enjoying your waterfront activities, read these articles next:

• 5 Best Ocean City Attractions and Activities That Are Hidden Gems [Maryland]
• 5 Fun Things to Do in Baltimore, MD: Off the Beaten Track + Tips
• Buying a New Boat: 5 Good Reasons Why You Should Do It Today!
• 7 Beach Essentials For Family: Quick Guide To Beach Packing
• Best Beach Vacation Capsule Wardrobe: 7 Packing Tips for the Coast
• Yoga By The Beach: 8 Easy Tips for The Best Experience