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8 Beautiful Chesapeake Bay Hidden Gems You MUST SEE

Looking for your next getaway? Check out these Chesapeake Bay hidden gems!

Get ready fellow explorers! Today, Must See Places is uncovering the most beautiful Chesapeake Bay hidden gems! In this article, we’ll delve into the stunning treasures nestled along the Bay’s scenic shores.

From charming harbors to serene beaches, each one offers a unique slice of heaven waiting to be explored. Whether you’re a history buff, nature enthusiast, or simply seeking a little escape from everyday life, there’s something for everyone along these shores.

Let’s dive in and unlock the beauty of these hidden treasures. Trust us, you won’t want to miss out on these “Must See” sights! Get ready to be amazed by the wonders of 8 Chesapeake Bay hidden gems, making memories that will last a lifetime!

… Pack your sense of adventure because these Chesapeake Bay hidden gems are calling your name!

Chesapeake Bay Hidden Gem
Photo by Jon Bilous at Shutterstock

Chesapeake Bay hidden gem: Chesapeake City, Maryland

A Bohemian colonist initially named Chesapeake City as The Village of Bohemia. However the name was changed in 1839 after the Chesapeake and Delaware Canals were constructed. Nowadays, it’s the only town in Maryland on a functional commercial canal.

Most of the beautiful Victorian architecture has remained intact. So, the town is registered as a historic site. There are many places to discover here, including Mount Felix Vineyard and Winery, the Chesapeake City Bridge, and the Historic District.

The C&D Canal Museum is an excellent way to understand just how important these waterways are and the significance of the canal system.

Chesapeake Bay hidden gem: Cape Charles, Virginia

Cape Charles is a historical town that boasts the most extensive collection of early 20th-century architecture on the Eastern Coast. Peach Street Books is a favorite among travelers and locals and a famous picture-worthy bookstore.

There are also charming museums and art galleries, like the Cape Charles Museum and the Ellen Moore Gallery. The Cape Charles Natural Area Preserve is where you’ll find 50 acres of outdoor activities and it’s perfect for a leisurely stroll.

The boardwalk is another fantastic spot that’s been well maintained and breezes through beautiful scenery. Looking for a place to stay? Hotel Cape Charles is an outstanding two-star, two-story, brick hotel.

It’s boutique-style and encompasses the spirit of Cape Charles, which is perfect for a short stay in this unique town.

Chesapeake Bay hidden gem: Havre De Grace, Maryland

Havre de Grace is located at the jaws of the Susquehanna River and the tip of Chesapeake Bay. It was named for the port city in France and is known nowadays as a friendly town with lots of things to see and do.

One of the most fun things to do is to check out First Fridays, when the downtown streets are closed down, and it draws a family-friendly crowd. You’ll be greeted with food trucks, live music, and local artisans selling their goods.

Other popular sites include the Havre de Grace Maritime Museum and the Friends-Concord Pointe Lighthouse, both of which highlight the maritime history of this charming coastal town.

Another interesting museum is the Lock House, initially an 1840s riverfront mansion. In fact, quite a few antique mansions have been converted into museums, making this small community even more outstanding.

Chesapeake Bay Hidden Gem
Photo by grandbrothers at Shutterstock

Chesapeake Bay hidden gem: Easton, Maryland

Easton is a Main Street Community on the Eastern Shore of Maryland known for its charming vibe. Since it was established in 1790, it has been well-known as the Sophisticated Center of the Eastern Shore.

Spring is our favorite time to visit when the flowers and trees begin to bloom, perfect for a trip through its historic downtown.

Some sites you shouldn’t miss downtown include the Frederick Douglass statue in front of the beautiful brick courthouse and the Academy Art Museum, which is one of many galleries in this artist’s retreat.

There are also many Victorian bed and breakfasts and historic inns where you can stay, including the Tidewater Inn and the Waterfront. Easton is one of the most culturally significant towns on the Chesapeake Bay and shouldn’t be neglected when visiting this region.

Chesapeake Bay hidden gem: Onancock, Virginia

Onancock is a small coastal town founded sometime in the early 1600s. Even though the town only has a population of roughly 2,000 people, it’s considered a place with lots of heart and even has a vintage movie theatre with an annual International Film Festival.

The lovely town is also known for its incredible art scene, which includes several galleries, including Danny Doughty and the Red Queen. There’s also an extensive collection of local glass blowers and a performing arts theatre, the North Street Playhouse.

Onancock also has stunning natural scenery, which is sort of expected for this area. The Onancock Sailing Adventures and the Tangier Ferry are popular sites if you’re looking for a fun time on the water.

There’s also a maritime museum celebrating the town’s history, Deltaville Maritime Museum, and one celebrating the history on shore, called Ker Place.

Chesapeake Bay hidden gem: Solomons Island, Maryland

Solomons Island, also known as Solomons, is close to Baltimore and is a fun weekend getaway for those living in the area, especially in the warmer months. One fun attraction is the Annmarie Sculpture Garden and Art Center, which includes a massive park.

If you’re enjoying the weather and you have the time, we highly recommend visiting Drum Point Lighthouse while here. It’s one of only four surviving Chesapeake Bay screw-pile lighthouses and once looked out over the entrance of the Patuxent River.

Nowadays, though, it’s an exhibit at the Calvert Marine Museum. A fun way to explore the island is by going on a Tiki Tour. These floating, thatch-roofed floats deliver stunning scenery and a cozy environment.

Solomons has long been known as a natural paradise for its gorgeous water and diverse biodiversity of plant and fauna species.

Chesapeake Bay hidden gem: Urbanna, Virginia

Urbanna is a friendly and quiet town with a walkable downtown area, colonial homes, and more boats than people! The name means City of Anne, and the town was named after Queen Anne.

Its other claim to fame is that it’s home to Virginia’s annual oyster festival, where local boaters, chefs, and other locals help the visitors learn to shuck oysters. The Urbanna Museum and Visitor Center is a fantastic spot to learn about the area and its history.

And the locals are pleasant and can also provide all the information you need while here. The best way to see Urbanna is on foot. So make sure you pack a pair of comfortable walking shoes!

If you’re walking around town, drop by Taber Park to check out the “LOVE” sign. You can even rent it for special occasions, making it a terrific photo opportunity.

Chesapeake Bay Hidden Gem
Photo by Ylexa Gabrielle at Shutterstock

Chesapeake Bay hidden gem: Saint Michaels, Maryland

Saint Michaels used to be a hub for oystering and shipbuilding. But nowadays, it’s a destination for water enthusiasts, boaters, and outdoor lovers. It’s also home to the historic landmark, the 1879 Hooper Strait Lighthouse, which is available for tours.

The Saint Michaels Museum, a restored house from the 1840s, adds some nostalgia to this charming seaside town. Another fun place to visit in Saint Michaels is the Classic Motor Museum, which hosts a few events each year, including Cars and Coffee, on certain days.

The best way to see this town is at a leisurely pace. Where can you stay? We recommend the Wildest Hotel. It’s right on the main drag, Talbot Street, and offers accessible trips on foot to the hub of the shops and restaurants.

Also on Talbot, you’ll find St. Michaels Winery, which is a lovely way to wind down after a full day of sightseeing.

Have you ever been to any of these Chesapeake Bay hidden gems? Be sure to share your experiences with our readers in the comments section below!

Meanwhile, Must See Places has many more fantastic vacation ideas for you. For instance, we highly recommend you check out: 9 Best Introvert-Friendly Destinations in the US for Peace and Quiet

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