21 Best Chesapeake Bay Things to Do for Great Fun

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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.

Chesapeake bay things to do
You’ll discover many great Chesapeake Bay things to do when you visit!

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

21 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. It’s the largest estuary in the US.

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 destinations has something unique.

So pack your bags, grab a map, and embark on an unforgettable journey through a comprehensive list 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]

native plant pollinator | Enjoy Travel Life
Tour the native plant communities that attract important pollinators at Adkins Arboretum.

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]

Sandy Point State Park | Enjoy Travel Life
There is something for everyone to enjoy at the expansive Sandy Point State Park.

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

Chesapeake Bay wine trail | Enjoy Travel Life
The Chesapeake Wine Trail offers a treasure trove of wineries!

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 wine tastings 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]

wild ponies of Chincoteague Island
You’ll enjoy breathtaking natural wonders to rich history in Chesapeake Bay.

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]

Cape Charles | Enjoy Travel Life
The Cape Charles Lighthouse as seen across the marsh.

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.

9. Smith Island, A Slice of History [Maryland]

Imagine biting into a multi-layer Smith Island Cake, the official dessert of Maryland. That’s just a taste of what awaits you on Smith Island.

It’s one of the Chesapeake Bay’s hidden treasures, rich in history and tradition. Hop on a ferry and step back in time.

You’ll love the sense of peace and the stories of this historic island community.

10. Northern Neck for Nature Lovers [Virginia]

Northern Neck at sunset
Northern Neck is a grat place to explore the great outdoors.

Dreaming of a place where the Potomac River meets the Rappahannock and flows into the Chesapeake Bay? The Northern Neck is your spot. It’s a perfect way to explore the great outdoors. Think miles of shoreline, delicious seafood, and nature at its best. Don’t forget your binoculars—eagles and ospreys are waiting!

11. Calvert Cliffs State Park [Lusby, Maryland]

You’re looking for more than just a beach day? Calvert Cliffs State Park offers that thrill of discovery with its ancient fossils hidden beneath your feet. Hike, swim, or simply relax by the water.

This place is a reminder of how wondrous nature can be, with its cliffs towering over the Chesapeake Bay.

12. Chesapeake Bay Maritime Museum [St. Michaels, Maryland]

St. Michaels isn’t just another waterfront town; it’s home to the Chesapeake Bay Maritime Museum. Here, every exhibit, boat, and artifact tells a story.

Dive into the bay’s nautical past and discover the hardy spirit of its people. It’s an experience that connects you to the Chesapeake Bay’s soul.

13. Virginia Beach: A Coastal Gem [Virginia Beach, Virginia]

Virginia Beach
Relax by the sea at Virginia beach.

Where the Chesapeake Bay meets the Atlantic Ocean, you find Virginia Beach. It’s a great place to embark on an adventure on the open waters or a perfect spot for a relaxing day by the sea.

You’ll discover the boardwalk lined with local restaurants and live music, making it an ideal place to spend your Friday afternoon. Just a short drive and you’re there, ready to soak in the vibrant atmosphere.

14. Craft Beer and Culinary Delights [Various Locations]

Dive into the local flavors of the Chesapeake. Beyond the fresh seafood bounty, you’ll want to explore quaint main streets for craft beer tastings and culinary delights.

Whether it’s one of the waterfront towns or any of the small historic towns in the region, each offers a unique taste experience.

Don’t miss out on local breweries for a sip of the region’s finest crafts.

15. Birding and Natural Wonders [Blackwater National Wildlife Refuge, Maryland]

Boardwalk at Blackwater National Wildlife Refuge
You’ll find excellent Virginia birding opportunities and more at Blackwater National Wildlife Refuge.

For nature lovers, the Blackwater National Wildlife Refuge is a treasure.

A short drive from the Chesapeake Bay, this refuge is a haven for wildlife and a prime spot for birding. Its vast land and waterways offer you a serene escape that truly showcases the beauty of the natural area.

16. Historical Exploration [Susquehanna State Park, Maryland]

Step back in time at Susquehanna State Park. Near some of the oldest towns in the United States, this park and historic district offers a glimpse into the American Revolution and the Chesapeake Bay’s cultural heritage.

The Havre de Grace Decoy Museum is a must-visit, offering unique insights into local traditions.

17. Sailing Adventures [Annapolis, Maryland]

sail boat moored in Chesapeake Bay
Go sailing in style on Chesapeake Bay.

Set sail from the Annapolis Yacht Club, where you can either sharpen your sailing skills or board a leisurely charter boat to journey across the Chesapeake Bay.

It’s the best way to breathe in the salty air and navigate the open waters.

It doesn’t matter if you’re an aspiring sailor or just looking to enjoy a day on the bay; Annapolis offers an unparalleled maritime experience.

18. Weekend Getaways [Chesapeake Bay, Various Locations]

Look to American Cruise Lines for a luxurious Friday afternoon escape on the Chesapeake Bay. It’s an ideal way for quality family fun or a serene getaway. Chesapeake Bay cruises offer a unique view of the bay’s stunning landscapes and historical sites. You’ll explore the area in comfort and style.

19. Outdoor Activities [Various Locations]

Embrace the great outdoors by kayaking in the Great Dismal Swamp, hiking through Northwest River Park, or wandering the trails of the Chesapeake Arboretum.

Virginia state parks offer endless opportunities for adventure in natural settings. Each park features the beauty of the region, inviting you to connect with nature in your own way.

20. Local Attractions [Virginia Area]

Cape Henry Lighthouse
Cape Henry Lighthouse is one of many local attractions worth visiting.

Don’t miss the Cape Henry Lighthouse for its breathtaking panoramic views and rich cultural significance. You can learn about local history while taking in the sights here.

Then, head to North Beach to experience its popular tourist attractions and relax in the charming city park. These local attractions offer a glimpse into the Virginia area’s diverse offerings.

21. Social Media and User Experiences [Chesapeake Bay, Wide]

As you explore the wonders of Chesapeake Bay, don’t forget to share your adventures on social media. Whether it’s your favorite spot for sunset views, a hidden gem you’ve discovered, or a memorable meal, your stories enhance the experience for others and help create a vibrant community of Chesapeake Bay enthusiasts. Use hashtags, tag locations, and engage with fellow travelers to make the most of your journey!

Final Thoughts on Chesapeake Bay Things to Do

So, there you have it—a comprehensive list of 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.

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

Happy travels!


Jackie Gately at the beach


About the Author: Jackie Gately

I'm Jackie Gately, your travel confidante and the creative force behind Enjoy Travel Life, awarded the "Best Casual-Luxury Lifestyle Blog (USA)" in Travel and Tourism by LUXlife Magazine for four consecutive years.

With 25 years of published expertise, I'm a seasoned writer, editor, and photographer curating inspiring travel guides and lifestyle tips for empty nesters. I hope to kindle your spirit of exploration, encouraging you to overcome obstacles and turn your dreams into reality.

Learn to minimize your pre-travel angst and maximize the joy of exploration with insights from my experiences. Let's make every adventure a celebration of this exciting phase of life! 

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Frequently Asked Questions about Chesapeake Bay Things to Do

Here are some commonly asked questions about things to do in Chesapeake Bay you may find helpful or insightful.

What makes Chesapeake Bay famous?

It’s the mix of stunning natural beauty, abundant wildlife, and rich history. From blue crabs to historic battles, Chesapeake Bay has it all. You’re going to find something that catches your fancy, guaranteed.

Should I visit Chesapeake Bay?

Yes, you should! Whether you’re after a peaceful day by the water, a taste of fresh seafood, or a hike through beautiful parks, Chesapeake Bay won’t disappoint. It’s a place that has something for everyone.

Can I swim in Chesapeake Bay?

Sure, you can swim here! Places like Sandy Point State Park are perfect for a dip. Just keep an eye on local water quality updates to make sure it’s safe.

What’s a major city on Chesapeake Bay?

Annapolis is the go-to city on the bay. It’s all about sailing, history, and waterfront dining. You’ll feel the nautical vibes as soon as you arrive.

Which cities are along Chesapeake Bay?

Annapolis, Baltimore, and Norfolk are your key cities. Each offers its own unique slice of bay life. You’ve got history, culture, and seafood galore.

Is Chesapeake Bay salty or fresh?

It’s a mix, actually! The bay’s waters blend fresh river water with salty ocean water, creating a unique habitat for all sorts of critters. It’s pretty cool how nature does that.

Do dolphins and whales visit Chesapeake Bay?

Yes, dolphins are pretty common, especially in summer. Whales? Less so, but it’s not unheard of. Keep your eyes peeled—you might just spot one.

What seafood is Chesapeake Bay known for?

Blue crabs and oysters are the stars here. Trust me, tasting them fresh from the bay is a whole other level of delicious.

Next Steps

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