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5 Reasons to Spend a Summer Weekend on the Chesapeake Bay

July 28, 2018
6 min read
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As part of a series on long weekend getaways, we’re showing you how to make the most of your summer Fridays, school breaks and the season’s extra-long days. Check back every week for inspired itineraries and easy city escapes.

While many Washington, DC metro-area residents opt to spend their beach days in Ocean City, Maryland or one of the Delaware beaches like Rehoboth, Dewey or Bethany, travelers too often overlook Maryland’s Eastern Shore — a stunning summer spot flanking the Chesapeake Bay.

The Eastern Shore is quieter than Ocean City, with fewer family-friendly activities and more nautical and historic appeal best enjoyed by couples looking for a romantic escape.

Our favorite town is St. Michaels, where the history can be traced back to the 1600s. It became infamous during the War of 1812, when locals tricked the British by hanging lanterns just outside the city, causing the Brits to miss their target. While the Colonial charm is hard to miss, there is also plenty of modern shopping, quality dining and activities that range from visiting a rum distillery to sailing and kayaking.

Best of all, it's a doable drive from a number of major East Coast cities: an hour-and-a-half from DC, two from Philadelphia and still reasonable three-and-a-half hours from New York City. (Keep a good card for earning points on gas purchases in your wallet, like the Citi Premier® Card. You’ll earn 3x points every time you fill up.)

Here are five ways to spend a long summer weekend in the Eastern Shore’s picturesque town of St. Michaels.

You can lounge at a luxurious resort

The Inn at Perry Cabin by Belmond is a historic property dating back to 1816 that was once owned by designer Laura Ashley and her husband, Sir Bernard Ashley. It was also the site of the main wedding reception in the movie "The Wedding Crashers." Recently refreshed by renowned designer Alexandra Champalimaud (who also reimagined The Plaza and The Pierre in New York City), the inn features French doors that lead to private decks, patios or verandas and nautically-inspired details.

Sprawling across 25 lush waterfront acres, the hotel has six sailboats and yachts for guests to use. Book our personal favorite package, “Skip the Bridge” ($865), which picks up guests before the traffic-clogged Bay Bridge from Baltimore–Washington International Airport (BWI), or from the Annapolis or Baltimore train stations and ferries them to the Inn aboard their custom Hinckley yacht, Five Star.

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Staff will greet you on board by sabering a bottle of Champagne, and you can complete your check in on the boat so, upon arrival at the Inn’s private dock, you can go straight to your room (a one-night stay is included in the package). Other amenities to take advantage of include the Inn’s kayaks and SUPs, the infinity pool and its adjacent bar, the brand new tennis courts and the just-opened 18-hole golf course, the Links at Perry Cabin.

You can visit a winery, distillery and a brewery all in one trip

St. Michaels might be quaint, but that doesn’t mean it’s not home to some boozy attractions. The St. Michaels Winery has a tasting room inside an old sewing factory building and makes wine from grapes grown in nearby Maryland vineyards — there’s Sauvignon Blanc, Pinot Gris, Merlot and Chardonnay to sip during your visit.

Right next door is Eastern Shore Brewing, which serves beers brewed on-site by Eastern Shore native, Zach Milash. (Order a pint of the harbor town's namesake beer, a malty amber ale.)

Behind them is the Old Mill District, home to the Lyon Distilling Company micro-brewery. Here, founders Jaime Windon and Ben Lyon specialize in spicy, well-balanced rums, along with corn, rye and malt whiskey.

You can order famous Maryland blue crabs — and oysters, shrimp and scallops

You can’t go to Maryland and not eat crabs! For a classic crab-shack experience, head to the Crab Claw, where fresh-caught seafood and Old Bay combine to create the tastiest crustaceans you’ll ever eat. And the harbors views aren’t bad either.

St. Michaels Crab & Steakhouse is another quality seafood spot on the water, while Chesapeake Landing Restaurant has a dining room as well as a market, if you want to cook your blue crabs at home.

For a break from seafood, try Ava’s Pizzeria & Wine Bar, Gina’s Cafe for Mexican and Theo’s for expertly cooked steak and pub fare. And save room for ice cream from Justine’s Ice Cream Parlour, a nostalgic spot with daily flavor combos and fun mash-ups, like a collaboration with Eastern Shore Brewing that produced Mango IPA sherbet earlier this summer.

You can learn about the local maritime history

The Chesapeake Bay Maritime Museum is a treasure trove for sea lovers, with everything from a working shipyard to a lighthouse dating back to 1879 that visitors can climb. There are also dozens of historic watercraft, a recreated crab-packing plant and exhibits on how the bay has evolved over the last century.

Plus, visitors can pull up an eel pot, catch blue crabs, tong for oysters and book a ride on the historic 1920 buy-boat, Winnie Estelle. Also on site is the historic Mitchell House, the home of the sister of Frederick Douglass, both of whom were born into slavery in Talbot County, where St. Michaels is located. As it happens, Maryland's governor, Larry Hogan, has declared 2018 the Year of Frederick Douglass to honor the bicentennial of the revered abolitionist's birth.

You can go for a ride on a skipjack, paddleboard or kayak

Just like you wouldn’t avoid hiking in Yosemite, it’s impossible not to set sail on the beautiful Chesapeake while in St. Michaels.

A ride on a skipjack — which became the preferred oyster dredge boat for the Chesapeake starting in the 1890s, but are very rare today — is a classic Bay experience. Try it by booking a ride on the H.M. Krentz, which offers daily cruises from the Crab Claw restaurant.

Visitors can also go on a sunset cruise aboard the vintage catboat, Selina II. At nearly 42 feet in length, the 1926 vessel is considered the largest surviving ship of its kind.

If you prefer a more active day on the water, rent a kayak or stand-up paddleboard from Shore Pedal and Paddle.

Featured image by Getty Images