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What's Up Magazine

The Great Chesapeake Loop

Mar 28, 2013 08:27PM ● By Anonymous

From south Bay villages steeped in watermen’s culture and rich in seafood to tucked-away towns that would make Jimmy Buffet smile with glee, we present eleven Chesapeake gems in what we’re calling the Great Chesapeake Loop—riffing off the concept of America’s Great Loop, a designed sail or cruise that loops national waterways in an impressive port-to-port excursion. While America’s Great Loop circles the Eastern portion of the U.S. (Atlantic coast, Gulf of Mexico, Mississippi River, and through the Great Lakes region), we downsized the trip within our very own Chesapeake Bay. Enjoy exploring these many ports of call this sailing season and report your experiences to, subject line “Chesapeake Loop.”


As you depart familiar waters of the Annapolis area, head due north toward the Upper Chesapeake, where our Loop begins in beautiful port of Chestertown. Surrounded by rich, plush farmland and Chesapeake Bay estuaries, colonial Chestertown is a prime getaway for boaters in search of relaxation. Escape city life and spend an afternoon strolling along Fountain Park, where the streets are lined with vendors selling flowers, vegetables, breads, arts, and crafts. Boaters will find Chestertown to be more than pleasurable, with its abundant deep water throughout the harbor and great selection of slips, docks, and anchorage. Dining experiences range from traditional cafes in the center of the historic district to contemporary-style cooking tapas and wine bars. Seafood specialties also are in ample supply, especially at the famed Fish Whistle, the only waterfront restaurant overlooking the Chester River.

Where to Dock: Chester River Yacht Club, Chestertown Marina, Mears Great Oak Landing, Tolchester Marina, Worton Creek Marina

Where to Dine: Along Cannon and High streets.

Rock Hall

Founded in 1707, Rock Hall began as an important tobacco port then turned into a major fishing and crabbing center. For boaters, this town offers 14 harbors and channels with deep water and another with shallow water. Although there is no anchoring in the harbor, nearby Swan Creek serves for ideal anchorage. Enjoy steamed hard crabs, seafood catches such as oysters and shrimp, or pasta dishes while dining dockside. After navigating into the harbor and docking, boaters also can enjoy a large selection of retail, from antiques and jewelry to fishing gear and souvenirs—you never know what treasures you’ll find, especially since Rock Hall has a renowned affection for all things pirate. Hop on the trolley and enjoy a tour of the town as you visit historical landmarks and top off your day with a visit to The Mainstay, a popular entertainment venue with live music.

Where to Dock: Cain’s Marina, Gratitude Marina, Haven Harbour Marina, Herrington Creek Marina, Lankford Bay Marina, Long Cove Marina, Moonlight Bay Marina & Inn, North Point Marina, Osprey Point Marina, Rock Hall Landing, Spring Cove Marina, Swan Creek Marina, The Sailing Emporium

Where to Dine: On and around Rock Hall Avenue and near the water.

Kent Island

Founded in 1631, Kent Island is the oldest English settlement within Maryland and the third oldest settlement in the U.S. This popular Chesapeake town is home to some of the best seafood restaurants on the Bay. With nine accessible marinas, boaters will find prime locations for slips and docking, most of which are close to the popular restaurants. Travel attractions such as the Chesapeake Country Scenic Byway and the American Discovery Trail draw in visitors to take pleasure in the scenic lifestyle of Kent Island, while the nearby Queenstown Premium Outlets provide a popular retail experience for finding designer goods at discounted prices.

Where to Dock: Bay Bridge Marina, Castle Harbor Marina, Kentmorr Yacht Yard, Kent Narrows Yacht Yard, Lippincott Marine, Mears Point Marina, Piney Narrows Yacht Haven, Queen Anne Marina, Wells Cove Marina

Where to Dine: Kent Narrows serves as a hub for restaurants on Kent Island.

St. Michaels

As a charming resort town, St. Michaels is a Chesapeake gem with a unique culture. Dating back to the mid-1600s, the town served as a trading post for local tobacco farmers and fur trappers. For modern day boaters, this destination is highly sought after, with it being home to five marinas, all of which offer slips, docking, and anchorage. After navigating through the deep harbor, where 150-foot yachts—like those owned by Johnny Depp—have been seen, hop off the boat and enjoy the many fine restaurants this town has to offer. Stroll down Talbot Street to find nautical handmade gifts and local artisan goods from a number of shops. Plan a day trip to St. Michaels Winery or Eastern Shore Brewing and enjoy locally produced wine and beer. Or hop aboard with a tour outfit for a historic cruise of area waters.

Where to Dock: Chesapeake Bay Maritime Museum, Higgins Yacht Yard, Miles River Yacht Club, St. Michaels Marina, St. Michaels Harbour Inn Marina & Spa

Where to Dine: Along Talbot Street and around the harbor


A quaint waterside village off the Chesapeake Bay with a population of 1,000, Oxford offers historic allure. Founded in 1683, Oxford is one of the oldest towns in America and has long been tied to its watermen’s heritage. For local boaters in search of solitude and relaxation, Oxford is a must-visit Chesapeake town. Home to primarily sailboats, this town is comprised of both deep and shallow water, with limited slips and docking, though nearby marinas offer more docking. Any boater will find Oxford to have less hustling and bustling entertainment, but it is surely not lacking in excellent dining and relaxation. Although shopping is fairly limited, sightseeing is a must for your to-do list. Visit the Oxford Museum, where a collection of the town’s treasures are on display, or take a ride on the Oxford Bellevue Ferry, believed to be the oldest privately owned ferry in the United States.

Where to Dock: Campbell’s Boatyards, Cutts & Case Shipyard, Hinckley Yacht Services, Mears Yacht Haven, Oxford Boatyard, The Masthead at Pier Street

Where to Dine: Restaurants are spread throughout town on Morris, Pier, and Tilghman streets, and on Oxford Road.

Tilghman Island

In the mid-Chesapeake Bay region, Tilghman Island is a working watermen’s village and an excellent source of local seafood. Nicknamed “Pearl of the Chesapeake Bay,” Tilghman is best known for being home to the last commercial fishing sailing fleet in the United States, with the skipjacks on display at Dogwood Harbor. There are several unique restaurants and retail shops on Tilghman, offering everything from local seafood to baked goods to fresh maple syrup. Join in on fishing charters, skipjack charters, lighthouse tours, cruises, or recreational rentals to get full participation in what Tilghman offers best.

Where to Dock: Harrison’s Country Inn and Chesapeake House, Knapp’s Narrows Marina & Inn, Tilghman Island Marina, Tilghman-on- Chesapeake Yacht Club and Marina

Where to Dine: Waterfront dining is available at marinas and inlets around the island.


With more than 515 slips, Crisfield is accommodating to all boaters, whether their choice of vessel be power or sail. Nestled near the mouth of the Little Annemessex River, Crisfield’s history dates back 1663, when it was originally named Annemessex Neck, coined after the tribe of Native Americans who once lived and hunted on the river. With three marinas in town, Crisfield offers slips, docks, and anchorage along the Bay. Visiting boaters can participate in outdoor activities such as exploring nearby Janes Island State Park—renowned for some of the best canoeing in the state—or taking part in a walking tour of the town. As the southernmost incorporated city in Maryland, Crisfield is known as a seafood town, relying heavily upon its fishing economy. For hungry boaters, look no further than the waterfront restaurants, where local catches of oysters and crabs are met with imported seafood to please any palate. Interested in learning about the Maryland state dessert? Almost all Crisfield restaurants serve the Smith Island Cake.

Where to Dock: Somers Cove Marina

Where to Dine: On and around Main Street

Solomons Island

A quiet waterfront fishing village like Solomons Island is the perfect destination for boaters in search of outdoor adventure. Located near Calvert Cliffs State Park, visitors can pan for ancient Megalodon shark teeth, explore the ancient cliffs, and enjoy some of nature’s fi nest scenery. It’s also home to two historic lighthouses, the Drum Point Lighthouse and Cove Point Lighthouse. Tie up at one of Solomons’ many marinas with ample slips and docks or opt for anchorage. Dine with the locals and enjoy live entertainment on the waterfront with gorgeous sunsets. Take some time to stroll the Solomons Riverwalk and visit nearby antique shops for unique treasures of yesteryear.

Where to Dock: Calvert Marina, Solomons Yachting Center, Solomons Island Yacht Club, Spring Cove Marina, Zahniser’s Yachting Center

Where to Dine: Waterfront dining is available around Back Creek and the Patuxent River inlet.

Chesapeake Beach

As the dream of developers from the late 19th century, Chesapeake Beach began as a grand resort on the Bay with a boardwalk, bandstand performances, a carousel, a casino, and The Great Derby, a rollercoaster that ran until the 1920s. Now, Chesapeake Beach echoes its past by providing the resort experience with a modern twist. Once docked at the accommodating marinas, there are several restaurants within walking distance that are known for the fi nest fresh rockfish in southern Maryland. Visit the Railway Museum for historic perspective, or bask in the lagoon at the Chesapeake Beach Waterpark. Fishing also is on the bill, as Chesapeake Beach is colloquially referred to as the “Charter Fishing Capital of Maryland.”

Where to Dock: Breezy Point Marina, Harbor House & Marina, Rod ‘N’ Reel Dock, Rod ‘N’ Reel Marina West

Where to Dine: Along Chesapeake Avenue, Bayside Road, Mears Avenue, and Bay Avenue

Herrington Harbor

Home to the largest privately owned marinas in Maryland, Herrington Harbor primarily provides deep channels of accessibility. Though accommodating to both power and sail boats, Herrington Harbor is primarily home to sailors. With two main marinas located on either side of Herrington Bay (on the western shore near Friendship and Tracey’s Landing), there are more than 1,200 slips. Divided into South and North Herrington Harbor, this Chesapeake treasure offers dining, marinas, and shops on each side and scenic views overlooking Bay waters. Known for being a departure point for dynamite Bay fishing, Herrington Harbor caters to charter parties and families. There’s also excellent shopping for locally produced wine, beer, and baked goods, especially in North Herrington Harbor, where you can spend the day sifting through antique shops or visiting specialty stores.

Where to Dock: At either the north or south location on Herrington Bay

Where to Dine: Each marina harbors two restaurants.


Considered the busiest recreational port on the Chesapeake Bay, Annapolis is a world-class destination with many slips within the City Dock vicinity and its 18 miles of surrounding shoreline. Home to both power boats and sailboats, Annapolis has seen many famous sailing vessels, some of which have even graced Hollywood films. As home of the Maryland State House (the oldest building in continuous legislative use in America), the U.S. Naval Academy, and St. John’s College, Annapolis functions as a modern city upon a historic backdrop. Waterfront seafood restaurants offer crabs, shrimp, oysters, and mussels in both traditional and custom-made dishes. Historic taverns grace Annapolis with daily specials, brews, and merriment, served with a side of history. Annapolis has dozens of shops that offer a variety of crafts and wares, from local boutiques that specialize in unique jewelry to modern retail shops. Learn more about this colonial town’s past by visiting the Annapolis Maritime Museum and HistoryQuest, or by participating in one of the many guided walking, ghost, or cruising tours.

Where to Dock: In and around City Dock via the Annapolis Harbormaster’s Office. Numerous private companies offer docking and mooring, as well.

Where to Dine: A variety of restaurants offering indoor and outdoor seating are located throughout downtown and around the harbor.