8 Of The Most Charming Towns In Chesapeake Bay
The Chesapeake Bay area is one of the most charming areas to visit if you love being near the water. It showcases a series of quaint little towns, each displaying their unique history, landscapes, and culture. If you’re considering a vacation in the mid-Atlantic region of the United States, Chesapeake Bay may just be the ideal spot for you and your family or friends.
You’ll surely enjoy some breathtaking views over the water while enjoying a good meal or visiting a museum in and around the area. But the best part about the Chesapeake Bay area’s charming towns is that they each provide you with an opportunity to meet the locals, stroll around the town, and take in those absolutely stunning water views. There are plenty of old towns to choose from, but we’ve collated the top eight small towns for you to consider for your trip.
Oxford, Maryland
This little town is the perfect postcard destination. Oxford is a port town and one of the oldest in the state of Maryland. The town hosts a plethora of historic buildings, and the main street in the downtown area hosts inns, restaurants, and historic monuments—one of which is the famous Robert Morris Inn. This was built in 1710 and boasts grand architecture in the heart of Oxford town. The inn is the longest-running fully-serviced inn in America, making it a must-see for tourists in the area.
If you enjoy history, a visit to the Oxford Museum is a great idea, a place where you can soak up the local history and view local artifacts as well as exhibits which were donated by the Oxford townspeople. Wander down the town’s main street to find a stream of old local businesses and homes displaying wonderfully manicured front gardens. Grab a seafood lunch at a local tavern or take a ride on the famous Oxford-Bellevue Ferry. If you’re there over the holiday season, make sure to look out for the Christmas on the Creek annual event!
Solomons Island, Maryland
Solomons, Maryland, also known as Solomons Island, is a prominent destination for tourists in search of beautiful marinas, decadent seafood restaurants, and cute little gift shops. It is located at the mouth of the Patuxent River and at the south end of the Governor Thomas Johnson Bridge, which stands at a massive 135 feet high and is the ideal spot to view this stunning town aerially.
This town is located in southern Maryland and hosts a wonderful waterfront and it’s best known as a boating hub. The main area of the town has a boardwalk that is ideal for views of the sunset against the water in the summertime.
Cultural enthusiasts must add the Annmarie Sculpture Gardens and Arts Center and the Calvert Marine Museum to their go-to list. Several live events are also held in the town each year, including events such as live musical acts. If you’re there in the early summer, you can enjoy being a part of the Solomons Dragonboat Festival.
Annapolis, Maryland
Annapolis, Maryland, is the capital of Maryland and is known for its naval heritage. This charming little town is home to the US Naval Academy, first opened in 1845. Today, tourists can walk its historic grounds while enjoying the quaint town. The town is located just 30 miles from Washington, D.C., making it easily accessible to most travelers. Annapolis displays the most wonderous 19th-century architecture and is appreciated by travelers year-round.
The town’s cobblestone streets take you to historic times, and the stunning harbor always gives its visitors some incredible views to enjoy. Annapolis is known to be a very walkable town, and people love strolling through the historic district, as well as several cafés, galleries, and boutique shops in and around the area. Visiting the Hammond House is a must. This house was built in 1774, and today, it’s a graceful museum that celebrates the town and the architecture that it hosts. If you’re a food lover, visit the Cantler’s Riverside Inn for a plate of the freshest blue crabs from Maryland itself.
Virginia Beach, Virginia
Virginia Beach is located on the southeastern coast of the state of Virginia, at the mouth of the Chesapeake Bay. This unique town offers visitors a day at the beach, hiking on stunning trails, or eating some of the best cuisine Virginia has to offer. The town has a wonderful oceanfront and boasts one of the longest sandy beaches in America, stretching for miles.
Virginia Beach is the perfect town if you’re looking for a place that offers a good range of water sports. You can also wander down the cement boardwalk while taking in the beautiful views and soaking up the sun. Stop at one of many local restaurants along the boardwalk for a taste of Virginia.
Nature lovers can enjoy a trip to the First Landing State Park or the False Cape State Park for a day filled with hikes and picnics. Wildlife is also a must-see in Virginia Beach. Visit the Pleasure House Point Natural Area to see over 115 acres of wildlife habitat and spend the day bird watching. There is something for everyone in this small but beautiful Chesapeake Bay town.
Cape Charles, Virginia
Cape Charles is a charming little town on Virginia’s eastern shoreline. In fact, it is the only town in this area home to a public beach on the bayside of the eastern shore. The town is famous for its fleet of fresh clams, oysters, and crabs. In 1884, it was established for the railroad industry and showcases several historic train sites and exhibits today.
Even though Cape Charles is not located on the Atlantic Ocean, it offers visitors the most stunning little beach with calming and shallow waters from the Chesapeake Bay. Visitors can enjoy a day kayaking on these still waters or go on a fishing trip. Other common activities in and around town include a day of golfing at Bay Creek. Children can also enjoy mini golf at the Cape Charles Mini Golf area.
This quiet and relaxing town has a historic downtown area with much on offer. Take a walk on Mason Avenue to see the famous Cape Charles Coffee House and lovely little shops along the way. The Cape Charles Museum and Visitors Center gives travelers a chance to learn about the town’s history while exploring its Victorian architecture throughout the area.
Onancock, Virginia
Onancock was founded in 1680. Although it may be a small town, it offers its tourists an abundance of history and culture. The town is located on the south end of the eastern peninsula in the Chesapeake Bay area.
People who stop by Onancock often enjoy the town's antique shops, souvenir stores, galleries, and restaurants. It’s also known for offering travelers an array of water sports, like kayaking. Visit the Historic Onancock Creek to sneak views of the watermen coming into the town with their catches of the day. You can also see a range of the most majestic birds in the area, including bald eagles, herons, cranes, and falcons.
History fans will love a day at the Watermen’s Museum and Research Center to learn all about the town’s history and its link to commercial fishing. Watch a movie at the Roseland Theater—a vintage movie theater built in the 1950s. Visit the wharf for a delicious crab cake or drink at a pub. No matter what you choose to do in Onancock, you will never be bored in this small but entertaining town.
St. Michaels, Maryland
St. Michaels is the ideal small town on the eastern shore of Maryland, where you can experience a wonderful bridge between historic and leisurely activities. Much like other towns on this list, St. Michaels can be accessed via the Chesapeake Bay Bridge Tunnel.
The picturesque little town is known as a little gem and allows travelers to enjoy long walks in and around the town center. Walk through St. Mary’s Square and take in the historic architecture of every building. If you’re interested in water-based activities, rent a kayak or go on a sailing tour to see the town from the water. You can also take a boat ride to Rock Hall for even more breathtaking views. The Chesapeake Bay Maritime Museum is unique as it is an 18-acre interactive museum boasting a massive display of Chesapeake Bay boats.
St. Michaels also offers food lovers the best and freshest oysters and crabs from the local bay area. The Crab Claw restaurant is ideal for this experience, as it is located on the waterfront and provides stunning water views with a delicious seafood meal.
Tangier Island, Virginia
This wonderful island is only accessible via air or water. It is Chesapeake Bay’s hidden gem and is considered the “soft shell crab capital.” Tangier Island is just a 10-minute ferry ride from the Onancock Wharf, making it easy to get to even though so many see it as a hidden island. Here, watermen have harvested oysters and crabs for generations, and visitors can enjoy the local fresh seafood at one of many restaurants in town.
The small, marshy town allows visitors to rent Tangier taxis (more commonly known as golf carts) or bikes to navigate the narrow streets car-free. While in the area, take in the pristine shores and enjoy a nature cruise through the intricate waterways network. For a good dose of history, you can also visit the Tangier History Museum, the Swain Memorial United Methodist Church, and the Crockett House.
Why Consider Visiting Chesapeake Bay’s Small Towns?
The Chesapeake Bay area is one of the most historic regions in the United States. As you can see, each small town along the Bay Area has various things to offer its tourists, and the region is always full of life from locals and visitors worldwide. If you’re looking for a small town to escape the hustle and bustle of everyday life, consider kayaking, boating, hiking, or eating at one of these Chesapeake Bay gems.
