6 Most Scenic Small Towns in Chesapeake Bay

Chesapeake Bay is the largest estuary in the United States, stretching hundreds of miles across Maryland and Virginia, where many of their rivers meet the Atlantic Ocean.

The region was vital to early Native American tribes and became an important center for European settlers to trade and thrive.

Its stunning scenery includes a diverse collection of wildlife, with shorelines ideal for sailing, fishing, and birdwatching. The bay truly is a haven for nature enthusiasts and outdoorsmen alike.

That beauty is enjoyed by the more than 18 million people who live in the region's watershed.

Read on to learn about six of the most scenic small towns in the Chesapeake Bay area.

Annapolis, Maryland

Annapolis is famous for being a top sailing spot in the U.S. It has an old-fashioned city center and a bustling culture around its waters, drawing sailors globally.

Its downtown still retains a classical, colonial feel, with cobblestone paths and centuries-old buildings. Main Street and Maryland Avenue are must-visits for their stunning display of the city's colonial past.

The City Dock is a lively spot right by the water where you can enjoy views of the bay and loads of interesting boats. At the docks, you can spot everything from small sailboats to big yachts, making it quite a sight to take in.

Another must-see place in town is the Maryland State House. It is one of the oldest government buildings in the USA, and it is still being used today. Its distinct wooden dome contrasts beautifully with the blue Maryland sky.

Oxford, Maryland

While it is not as acclaimed as its England-based namesake, Oxford in Maryland has its own depth of historic beauty to experience.

One of the best ways to explore the heritage Oxford offers is through a historic walking tour. You can pick up a map at the Oxford Museum or download one online.

On this self-led journey, you will wander by old houses, churches, and important spots, getting a peek into the town's history.

Speaking of the museum, right in the town's center, the Oxford Museum invites you on a fun journey through the region's seafaring past, its local stories, and cultural treasures.

After, hop on the Oxford-Bellevue Ferry for a journey on the water. It is among the oldest ferries in the country, and it is run by private owners. This ferry offers you a peaceful and easy way to get across the nearby Tred Avon River, and it will be a moment that will not be forgotten soon.

Irvington, Virginia

Fancy an oyster or two? Irvington is right next to the Rappahannock River, famous for its oyster beds. Tours are even offered to show how they are farmed and how vital oysters are to the overall aquatic environment.

The town's strong connection to ocean history is celebrated at the Steamboat Era Museum. People who visit can check out displays about the times when steamboats ruled the Chesapeake Bay. You can find cool stuff like antique and authentic items, important photos, and hands-on activities.

After oysters, try some wine. At The Dog and Oyster Vineyard, wine lovers get a special treat. This stop is well-known for its top-notch wines and beautiful sights.

The historical Christ Church & Museum, located just north of Irvington, is a window into the region’s colonial times. The grounds include the iconic church from 1735 and retain its timeless features like its brick door frames, tall seats, stone flooring, and much more.

Solomons, Maryland

Solomons lies on a peninsula, jutting out into the water, and is found at the very bottom of Calvert County. The town has the Patuxent River on its west side and the big Chesapeake Bay on its east.

In town, the Solomons Island Boardwalk is an excellent spot to get river views. It has shops and places to eat along its path, and ideal for a relaxed walk and watching boats sail past.

Solomons has the Calvert Marine Museum, an informative stop-off teaching the area's maritime legacy. People can explore exhibits on local paleontology, with ancient animal fossils waiting for you to discover.

A trip to Solomons is not done without checking out the Drum Point Lighthouse. This old, fixed-up lighthouse has tours that tell you about its part in history by the sea and lends out unbeatable views of the Chesapeake Bay from up high.

Onancock, Virginia

If you love the outdoors, Onancock is the town to see. Onancock sits close to Tangier Sound, with its clear waters and bountiful sea creatures.

The town is also within reach of the scenic Eastern Shore Barrier Islands. These islands are acclaimed for their natural environments, such as beaches, sand hills, and wetlands.

You can reach these islands by boat, and they are a memorable experience for those who love nature and enjoy exploring places.

In the heart of the town stands the Roseland Theatre, an old movie theatre that has been a favorite spot for fun since it opened its doors in the early 1900s.

Another gem is Ker Place, which dates back to the early 1800s. Today, it acts as a museum where you can explore local history, architectural wonders, and stunning decorative pieces.

Chesapeake City, Maryland

This small but pretty town is home to about 700 people and is found right where a canal links the Chesapeake Bay with the Delaware River.

Much of what makes Chesapeake City special ties back to the canal. It played a big part in how the town developed and flourished.

There are no better places to learn about that than the C&D Canal Museum. You can learn all about the canal through exhibits, old artifacts, and interactive activities. It shows just how crucial this waterway was for moving ships and goods.

The Chesapeake City Bridge is a standout place in town, shining over the lovely water below. It is a fixed, high-arch bridge built back in 1949

Right along the canal, you can find old Lock Keepers' Houses. These houses were once home to the people who managed the water locks and gave us a peek into the town's history with ships and water.

Discover Chesapeake Bay's Coastal Charm

All of these towns tell a story of life by the sea and reflect the importance of Chesapeake Bay to the region and country.

The towns are full of old-timey classic buildings, museums about boats and fishing, unforgettable walking paths by the water, and sailboats drifting across the water.

They all have their unique flavor, but together, they make up a beautiful area along the Maryland and Virginia coastline that is rich in history and culture.

So, no matter what town you decide to visit, you will leave with some of the best memories that the Chesapeake Bay region can offer.