9 Best Things to Do in Chesapeake Beach, MD

By VI Staff on June 25, 2021 - Updated

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Chesapeake Beach is a lovely town in Calvert County, Maryland, originally established as a resort community in the early 20th century. During the peak of its resort heyday, the town anchored Maryland's "Little Nevada" district, home to glamorous hotels, slot machines, and boardwalk attractions. Though most of its Gilded Age resort attractions are gone today, visitors can still learn about the region's history at sites like the Chesapeake Beach Railway Museum or stroll its gorgeous Chesapeake Bay boardwalk, pier, and shoreline throughout the year. Excellent seafood restaurants abound, serving up Chesapeake-caught crab, fish, and seafood classics. Hours/availability may have changed.

1.The Chesapeake Beach Rail Trail

The Chesapeake Beach Rail Trail is a rail-to-trail connector trail network located along the route of the former Chesapeake Beach Railway, which operated between 1900 and 1935 and served as a popular transportation route to the beachfront resort attractions of Chesapeake Beach. The railway corridor was redeveloped by the Maryland-National Capital Park and Planning Commission and now showcases the region's stunning marshland and creek areas for area walkers, joggers, and cyclists. Much of the trail sits atop a wooden boardwalk over Fishing Creek, creating unique natural panoramas for travelers. Many of the area's attractions are accessible via the trail, including the Chesapeake Beach Railway Museum, located at the trail's trailhead.

2.The Chesapeake Beach Railway Museum

The Chesapeake Beach Railway Museum is a lovely cultural museum preserving the history of the Chesapeake Beach region, housed within the city's former Washington and Chesapeake Railway Company railway station. The National Register of Historic Places-listed property was originally erected in 1898 and operated through the spring of 1935, noted as one of the most prominent examples of rural railroad architecture remaining on the East Coast. Today, the station has been converted into a local history museum, showcasing the history of the region's bayside resort and beachfront district via audiovisual presentations, photography, and interactive exhibits. Exhibits include a collection of collected boardwalk artifacts, a retrospective of railroad entrepreneur and town planner Otto Mears, and the "Dolores" parlor car that formerly operated on the Chesapeake Beach Railway.

4155 Mears Ave, Chesapeake Beach, MD 20732, Phone: 410-257-3892

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3.Daydreamer Sportfishing, Chesapeake Beach, MD

Daydreamer Sportfishing offer group charter fishing excursion on the waters of the lovely Chesapeake Bay aboard the Daydreamer, a 38-foot Bertram charter boat designed by world-renowned yacht architect Ray Hunt. The lovely boat is decked out with twin 2006 Cummins diesel engines, a full galley, and an indoor air-conditioned salon with a television and private shower. Anglers can enjoy excellent opportunities for fishing throughout the year for rockfish that grow up to 50 pounds in size. Penn and Shimano tackle are offered for standup or trolling, while a full tuna tower is equipped with Raymarine electronics and a full GPS system.

4165 Mears Ave, Chesapeake Beach, MD 20732, Phone: 703-477-5272

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4.Katherines Charter Fishing, Chesapeake Beach, MD

Katherines Charter Fishing offers full-day and half-day trips aboard a gorgeous Coast Guard-certified boat with seating for groups of up to 30 people. The company operates two charming fishing charter boats, including its namesake Katherine, which was designed under the supervision of Bootie Collins and can reach top speeds of 20 knots. The company's Katherine II features state-of-the-art electronics within a 45-foot Carman fiberglass baybuilt-style structure. Anglers can make use of the boats' comfortable dinettes, which seat six people, and temperature-controlled cabin with full steering controls. All rentals include licenses, tackle, and optional fish cleaning services. Alcohol, food, and beverages are permitted on board.

3748 Harbor Rd, Chesapeake Beach, MD 20732, Phone: 240-676-1098

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5.Chesapeake Windsail Cruises, Chesapeake Beach, MD

Chesapeake Windsail Cruises embark from the gorgeous seaside town of Chesapeake Beach and offer day sailing excursions on the waters of the stunning Chesapeake Bay. The charter company offers daily sailing cruises aboard the stunning Eternal Hope, a Coast Guard-certified 42-foot yacht. Passengers can see amazing area natural wonders like the historic Cliffs of Calvert from the yacht's decks or enjoy chances to spot marine wildlife like dolphins and ospreys on the bay's waters. Cruises last approximately two and a half hours, embarking throughout the day Tuesdays through Sundays between mid-May and October. After the cruise, passengers can dine at the delicious partner Rod 'N Reel Restaurant, which serves up some of the area's best seafood entrees.

4160 Mears Avenue Dock A, Slip 15, Chesapeake Beach, MD 20732, Phone: 855-561-8810

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6.Kyran Lynn Charters, Chesapeake Beach, MD

Kyran Lynn Charters are one of Chesapeake Beach's top fishing charter companies, operating out of the city's Rod 'N Reel Marina. The company offers excursions traveling as far as locations such as Annapolis, Solomons Island, Tilghman Island, and Deale aboard its Kyran Lynn charter boat, helmed by Captain Marty Simounet. Dinner cruises travel to nearby Harrison's Chesapeake House on Tilghman Island, serving up excellent seafood fare and exploring the beautiful waters of Maryland's Chesapeake Bay coastline. The bay's waters offer some of the East Coast's top chances to catch striped bass, doormat flounder, big gray trout, and other bottom-dwelling fish species.

4165 Mears Ave, Chesapeake Beach, MD 20732, Phone: 410-474-4105

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7.Big Worm Fishing Charters

Big Worm Fishing Charters are helmed by Captain Drew "Worm" Payne, taking up to 49 passengers on fishing excursions throughout the Chesapeake Beach, Kent Island, Annapolis, Baltimore, and Northern Virginia areas of the Chesapeake Bay. All excursions are offered aboard the gorgeous Big Worm 52-foot deadrise charter vessel, which was custom-constructed by Millennium Marine and has been inspected by the United States Coast Guard to ensure top safety standards. Throughout the year, passengers can enjoy prime opportunities for catching striped bass, rockfish, speckled trout, bluefish, and black and red drum on the waters of the bay. The charter service is a great choice for team-building events, lunch and dinner cruises, bachelor and bachelorette parties, and other private special events, offering onsite DJ services and catering options.

3150 Karen Dr., Chesapeake Beach, Maryland 20732, Phone: 410-474-4428

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8.Traders Seafood Steak and Ale

Traders Seafood Steak and Ale has been a local favorite dining destination in the Chesapeake Beach region for over half a century, originally opened as the Seabreeze in 1956 by Bill O'Mara. Since 2000, it has been owned and operated by Jim and Gary Luckett, serving up casual Chesapeake Bay seafood favorites at reasonable prices. It has been voted as Chesapeake Beach's Best Breakfast, Best Deck Dining Destination, and Best Nightlife Option by regional newspapers. High-quality seafood favorites like crab Imperial, Maryland crab cakes, and fried butterfly shrimp platters pair with gourmet pub burgers, sandwiches, and appetizers. At breakfast, diners can enjoy three-egg omelettes, Belgian waffles, or homestyle favorites like sausage gravy and biscuits. Keno, Racetrax, and Maryland lottery games are offered, along with electronic bingo and live music night events.

8132 Bayside Rd, Chesapeake Beach, MD 20732, Phone: 301-855-0766

9.Ledo Pizza

Ledo Pizza has been a tradition in the Chesapeake Bay region since 1955, originally founded in Adelphi, Maryland. Today, the franchise operates several locations throughout the Baltimore and Annapolis regions, including a location in Chesapeake Beach's downtown district. The chain is known for its high-quality fresh rectangular pizzas, crafted with homemade dough, gourmet cheese, and traditional Italian tomato sauce. Menu favorites range from traditional pizza varieties like thick-cut pepperoni to unique takes like tzatziki, Korean barbecue, or hot honey pizzas. Shareable appetizers like panko-breaded shrimp pair with gourmet calzones, strombolis, and cheesesteak subs or pitas.

8416 Bayside Rd, Chesapeake Beach, MD 20732, Phone: 410-257-1705

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