Explore & Enjoy…

Herrington Harbour offers activities for all ages. Enjoy paddleboard and kayak rentals, tennis, volleyball, onsite beaches, sailing lessons, charter fishing excursions, an eco-trail, restaurant, deli and swimming pool. There’s something for everyone while staying at the Inn at Herrington Harbour. Just down the bay, the town of North Beach offers antique shops, boutiques, restaurants, bars, farmers markets, festivals, local wineries and breweries, golf courses, beaches, ice cream shops, waterpark and so much more Chesapeake Bay fun … Lots to do for an exciting destination wedding weekend or corporate retreat!

Herrington is surrounded by some of the most beautiful countryside in all of Maryland. Nestled right on the Herring Bay along the Chesapeake, Herrington on the Bay has access to fantastic Beaches, Wineries, Golfing, Breweries, and some of Maryland’s finest Dining. Whether you’re planning a stay and play eco-lifestyle wedding, or an extended corporate retreat, a full week’s stay at Herrington will never have a dull moment with activities for all ages, all within a short drive.

Scroll down to see more local activities or click on the menu tabs below.



North Beach

Within 10 minutes by car, this charming beachfront town offers something for all ages. Enjoy the beach and it’s ½ mile boardwalk by foot or bicycle, kayak or paddleboard by day, and for the evening crowd — free movies, concerts and campfires on the pier. You’ll also find great dining and shopping, and a famous Friday night Farmer’s Market 6-9pm May through October.

Chesapeake Beach

Just about one mile south of North Beach, Chesapeake Beach is another quaint town with a beautiful beach, more waterfront restaurants and succulent seafood. Learn more about the town’s history on the Chesapeake Beach Historic Trail, a self-guided walking tour through town marked with wayside informational signs.

Other public beaches

Bay Front Park (Brownie’s Beach)

During the summer months, from Memorial Day weekend through Labor Day, there is a fee for non-town residents to use the Park (see below). The Park opens at 6am and closes at 9pm.

Breezy Point Beach and Campground

Breezy Point Beach and Campground is a most popular destination and serves a high volume of visitors during summer weekends and holidays. To ensure the safety of our visitors and protection of the facilities, the park has a limited capacity.

Charter Fishing Trips

Chesapeake Fishing Charters.com

We are located in Chesapeake Beach, Maryland. Our boats are all skippered by experienced Captains and crews, most of whom were raised on Chesapeake Bay fishing. Our boats can accommodate parties or groups of all sizes from the traditional angler 6-pack to a party of up to 36 anglers.

Wound Tight Sportfishing

Wound Tight Charters is based in Chesapeake Beach, Md, and is operated by me, Capt. Shawn Gibson. I manage this site and try to keep all information up to date. During the fishing season you will find pictures and video from recent Chesapeake Bay fishing charters as well as fishing reports to let you know what species of fish are being caught and where.



Greenspring Brewing Company

Greenspring Brewing Company is a small specialty brewery located in Calvert County, MD. We believe that beer is a perfect combination of art, science and cheer.

Jail Break Brewing

Jailbreak is a freedom expression. Beginning in 2013 and becoming fully operational in 2014, our artfully crafted beer is meant to be an escape from whatever drama is present in your life.




US NAVAL Academy

As the undergraduate college of our country’s naval service, the Naval Academy prepares young men and women to become professional officers of competence, character, and compassion in the U.S. Navy and Marine Corps. Naval Academy students are midshipmen on active duty in the U.S. Navy.

Annapolis Tours by Watermark

Annapolis Tours℠ by Watermark® is the authentic provider of guided historic walking tours in Annapolis, Maryland, on the grounds of the United States Naval Academy and the surrounding area.

Maryland State House

THE BEAUTIFUL MARYLAND STATE HOUSE is the oldest state capitol still in continuous legislative use and is the only state house ever to have served as the nation’s capitol. The Continental Congress met in the Old Senate Chamber from November 26, 1783, to August 13, 1784.

Schooner Woodwind Annapolis Sailing Cruises

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay.

William Paca House & Gardens

The William Paca Garden is a two acre oasis of natural beauty in the bustling center of Annapolis’ Historic District. Although many colonial Annapolitans had gardens, only Paca’s has been returned to its original splendor and opened to the public.



Renditions Golf Course

Championship golf featuring carefully crafted replicas of 18 holes that have defined the history of the game. Play a round of golf unlike any other. Imagine a golfing experience that would take you from the heather of the Scottish links to the azaleas of Georgia.

Chesapeake Hills Golf Course

Chesapeake Hills Golf Course is Calvert County’s premier public golf course. Located in scenic Lusby, Maryland and just minutes from historic Solomons Island, the course offers an enjoyable and challenging experience for all golfers.

Lake Presidential

We welcome golfers with disabilities. The course will make reasonable accommodations to ensure that golfers with disabilities are able to enjoy the course. Please contact the General Manager or Head Golf Professional at the course for more information.




Eat Chesapeake

The story of Chesapeake really started in our home kitchen. Making recipes for the family, hearing what they thought, and what we could all bring to the table as a family owned and operated restaurant.

Sweet Sues Bake Shop

From simple to spectacular, award-winning Sweet Sue’s stunning creations are the centerpiece of any special event.

Trader’s Seafood Steak & Ale

Although the name implies seafood and steaks, Traders is well known for its incredible breakfast, and features an enormous breakfast buffet on Sunday mornings from 7:00 am until 1:00 pm.

South County Café

South County Cafe is a favorite to locals in Deale. Serving delicious breakfasts and great lunches from soups to salads, sandwiches and more. People enjoy our collection of rustic antique décor — featuring a rustic barn wall, with a real tin roof and wooden pier, accented with hand painted and personalized signs.

Lunch and Dinner

Skipper’s Pier

Waterside Restaurant and Dock Bar. Step out onto the deck and you’ll find yourself enchanted with the boats, the birds, and the unparalleled views of the Chesapeake Bay.

Dockside Restaurant and Sports Bar

Located on Rockhold Creek in Tracy’s Landing Maryland, we are open seven days a week. Lunch & dinner are served daily. Breakfast is served Saturday & Sunday 7:00 to 12:00. We offer indoor seating year round and outdoor dining in the spring and summer. The Sports Bar is open all year round.

Happy Harbor

Walk-Ins Welcome, Good For Groups, Good For Kids, Take Out, Catering, Waiter Service and Outdoor Seating

Abner’s Crab House

Abner’s Crab House & Marina is located in the beautiful Chesapeake Beach, Maryland. Surrounding cities include Annapolis, Washington, and Prince Frederick!

Groceries & provisions

Chesapeake Market and Deli

The story of Chesapeake really started in our home kitchen. Making recipes for the family, hearing what they thought, and what we could all bring to the table as a family owned and operated restaurant.

Chesapeake’s Bounty

We believe in the health and economic benefits of local food, supporting local farmers, watermen, and other producers and paying fair-market prices (or better) for their products.


Full service supermarket specializing fresh cut USDA choice beef, handpicked produce, and personal customer service. Our family has been in the grocery business since 1961 and are committed to providing the wants and needs of our customers in a convenient, friendly setting.

North Beach Farmer’s Market

Nestled on the Chesapeake Bay’s western shore at the northern tip of Calvert County, the Town of North Beach epitomizes “land of pleasant living.” The town and its residents take great pride in the unique and colorful past, eclectic special events and diverse recreational opportunities.



Thanksgiving Farm

Thanksgiving Farm Vineyards & Winery is a Family Owned and Operated Business Dedicated to Grape Growing and Wine Making

Dodon Vineyards

Established in 2007, our vineyards are fortuitously situated on rolling hills just south of Davidsonville, Maryland.

Fridays Creek Winery

Fridays Creek Winery is located in Southern Maryland’s Calvert County just 17 miles from the Capital Beltway.

“What a beautiful place to enjoy the most important day of your life! We were married in the Herring Bay Bridal Garden, our ceremony was inside the Yacht Club, our rehearsal dinner was outside in the tent, our after party was at Mango’s next door, and we stayed at the Inn for two nights. Everything was absolutely perfect!! Our assigned coordinator helped us to create the most amazing day and memories. A great investment. All of our guests have raved about our wedding day at Herrington!!”

— Ashley + Mike

Get in Touch With Us

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