Living in Chesapeake Beach

Chesapeake Beach is a small community located in southern Maryland just minutes from Upper Marlborough along the Chesapeake Bay. It’s bordered by Woodland Hills, North Beach, and Annie Hall in Calvert County and is home to about 6200 residents.

Locally known for its Chesapeake Beach Railway Station and trail, Chesapeake Beach got its start back in the late 19th century with the plan for a grand resort on the shores of Chesapeake Bay. The state of Maryland granted a charter to Washington and Chesapeake Beach Railway Company in 1891 and in 1894, they were granted a charter to incorporate the town of Chesapeake Beach. Up until 1930, Chesapeake Beach was a thriving independent community. Many people would come from all over Maryland and the Washington DC area for day trips and steamboat rides along the Dixie and Dreamland. The small resort consisted of a boardwalk, park, picnic areas, bandstands, amphitheaters, roller coasters, vendors, and amusement rides.

In 1930, Seaside Park opened and all the amusements were moved to land rather than over the water. In the late 1940s, management changed once again in the park would be known as Chesapeake Beach Amusement Park until it closed in 1972. Today, the small town still attracts visitors nationally and internationally. It’s known for its Chesapeake Bay seafood Festival with delicious Maryland Blue crabs, fresh-cut rockfish, oysters, public boat ramps, local tackle shops, and charter fishing tournaments all up and down the Chesapeake Bay.

Chesapeake Beach Schools

Chesapeake Beach is part of the Calvert County public school system and most residents with school-age children are assigned to the Beach elementary school, Plum Point or the Windy Hill elementary school, the Windy Hill middle school, and the Northern high school. All of the schools received excellent reviews and ratings from parents and students alike. Some of the southern homes are served by the Huntingtown high school as well, which also receives excellent marks.

“Our fourth child is currently attending Northern High, a sophomore, graduating in 2017. Our first child graduated in 2008, our second in 2010, our third in 2014. I cannot say enough good things about the math program!! They have a fabulous AP Calc teacher, our child’s junior year class, AP Calc AB all received 4’s and 5’s on the AP exam.“

You don’t have to live in Chesapeake Beach to enjoy it but a lot of people find that living here is really one of the best ways to enjoy all the Chesapeake Bay and Chesapeake Beach have to offer. Because it was originally a resort community, any people still flocked to the area to enjoy the beaches, the boardwalk, peer and the shoreline throughout the year. The Chesapeake Beach Rail Trail is still a widely used trail network located at the route of the former Chesapeake Beach Railway. It’s perfect for walking, jogging and bicycling and much of it is over Fishing Creek, creating a natural and beautiful viewpoint for travelers and visitors.

The Chesapeake Beach Railway Museum is also a wonderful glimpse into the area’s history showcasing the region’s bayside resort and beachfront district. If you love sports fishing, Chesapeake Beach is a great place to head out on a charter fishing boat. Try your hand at catching the area’s rockfish the can grow up to 50 pounds in size. Larger charter boats can seat groups up to 30 people. Most rentals include licenses, tackle, and optional fish cleaning services.

Not into fishing but still want to enjoy the water? Check out a Chesapeake WindSail cruise and browse up and down the coastline of the Chesapeake Bay. You might spot marine wildlife like dolphins and osprey or grab dinner at one of the delicious restaurants up and down the coastline.

Chesapeake Beach has multiple shops and restaurants in the darling little downtown area. Traders Seafood Steak & Ale is an area favorite. Enjoy their seafood platters, breakfast, lunch, or dinner, delicious cocktails and fresh-caught, local seafood. This has been a local favorite for decades.

The Wheel House Beer Garden is another local favorite and a favorite for visitors alike. Maintaining its consistent five-star status, this great Chesapeake Beach restaurant features iconic handcrafted cocktails, delicious Cuban sliders and smoked bluefish, and a classic Sunday brunch with huevos rancheros, chorizo gravy, and endless mimosas.

Chesapeake Beach MD Real Estate & Homes For Sale

There’s a price point for just about everyone if you’re looking to live in this gorgeous little bayside coastal town. From condominiums and townhomes starting at around $200,000 to single-family homes between $300,000 and $600,000, there’s a variety of styles, colonial properties, new construction, mid-century homes, and ramblers to choose from.

We love to help you find the perfect home in Chesapeake Beach or surrounding southern Maryland areas.