Summer on the Water: 5 Nautical Journeys on the Chesapeake Bay

An idyllic summer weekend on the water is waiting for you in Rock Hall, a small harbor town in Maryland known as The Pearl of the Chesapeake. A local shares tips on the best ways to get out on the Bay.

CHESAPEAKE BAY – Most summer traffic driving through Maryland joins the crush towards the Atlantic Ocean, bound for Ocean City in Maryland, or Rehoboth in Delaware. But those in the know who want a more relaxed vibe drive along the two-lane country route to the Delmarva Peninsula’s northwestern region. This is farm country. For me, the vacation starts right here on the road, passing gently swaying cornfields, wide-porched farmhouses, and pockets of rural towns where the 25 mph speed limit makes the concept of slowing down tangible.

Maryland’s Rock Hall is a hidden gem isolated on an end-of-the road peninsula jutting out into the Chesapeake Bay. I called Rock Hall home for two years, during which time the steady hum of lawnmowers and abundance of maritime folk art — brushed metal Great Blue Herons, rusty anchors, buoys hooked across weathered fishing nets — were seared into my memory. No matter where you are in town, the water is never far; osprey and bald eagles soar in the sky.

There’s a particular flavor of freedom that only exists on the water. Being on a boat adds a specialness to everything that happens there. The water’s rise and fall feels so unusual for those of us who live our lives on land. Here are five ways to access perspective-shifting, seafaring adventure on the Chesapeake. Even if you don’t own a boat.

Paddle Eastern Neck Island

Rock Hall has some of the best water access you’ll find anywhere, with a wealth of portages throughout town. Rent a kayak or stand-up paddle board from Chester River Kayak Adventures, located on Main Street, for a full or half day. Then continue driving down Main Street for seven miles, and you’ll cross into the Eastern Neck National Wildlife Refuge.

Eastern Neck’s wildlife is enchanting. While quietly gliding through the water, look for barn swallow nests made of mud and grass underneath piers. You may glimpse herons lifting off from across a marsh, furry otters swimming up ahead, or a cownose ray swimming down below. Once back on land, take a nature walk on the BayView Butterfly Trail and watch for American Lady and zebra swallowtail butterflies flitting around the native flowering bushes.

Bogles Wharf is a great kayak launch if you’re paddling around the refuge on your own. Alternatively, you can book a guided kayak tour with Jim, longtime Rock Haller and owner of Chester River Kayak Adventures.

Charter an Overnight Sail

Shardana Sailing Charters can provide your personal floating hotel for the night. The charter begins anytime you choose and ends 24 hours later. A seasoned skipper captains the well-appointed, 43-foot Catalina 425 sloop, so all you have to do is bring your playlist, delicious food, and your crew. There’s a kitchen, a barbecue, and even an ice cream maker.

After dark, the Western Shore twinkles with lights from Baltimore and Annapolis. Let the water sway you to sleep in one of three comfy staterooms. When you wake up refreshed, try a stand-up paddle board yoga session before setting out your brunch spread: bagels, cream cheese, cinnamon rolls, and grilled Langenfelder farm-fresh sausage links from Chester River Wine & Cheese Co. Finish your cruise lounging on deck with an iced coffee in one hand and a paperback in the other.

Charter a Private Fishing Trip

Captain Wayne, of Wayne Gatling Guide Service, is a fourth-generation fishing charter captain, and before the term “fishing charter” came into vogue these excursions were called fishing parties. To book one, you’ll want to round up six or more of your most fun, or most contemplative, friends. You bring the food and drinks for the group (extra points for sharing with the captain and first mate) and Captain Wayne brings the tackle, fishing rods, and bait. And the boat! He brings the boat, too.

Most people who fish with Captain Wayne during the summer are repeat customers — some have been fishing with him for decades — but it’s also totally fine if you’re a first-timer. The usual catch is about two rockfish per person (it’s also the state limit). At 28 to 35 inches each, that’s a substantial amount of fresh fish. Bring a small carry-on cooler with ice, and while you hang out under the shade of the canopy, Captain Wayne will fillet the fish onboard and package it so it's ready to be cooked or frozen. Another fun option is to bring your rockfish to Waterman’s Crab House and have them cook up your catch of the day any way you like and serve it on the restaurant’s waterfront deck.

Learn How to Sail

In a two-hour experience with Rock Hall Yacht Club, a sailing instructor will teach you how to capture the wind and handle a sailboat in Langford Bay, a tributary of the Chesapeake. Learn as much as you want about tacking, gybing, the boom, and how to read wind direction. Once you’ve had enough, feel free to sit back and enjoy the breeze on your face while the instructor maneuvers the sail. The experience, called the Family Sail, is designed as a combination of learning and relaxing for up to three people at a time (including kids).

Take a Sunset Cruise

Captain Mark and First Mate Suzanne, quintessential storytellers and part-time pirates, are full of Bay knowledge. Book Blue Crab Charters and spend 90 minutes chatting with them about anything and everything from the ospreys flying overhead to the working fishing boats in the harbor to the hits of Jimmy Buffet. Their convivial hospitality is undoubtedly a key reason why Blue Crab has won Best in the Bay more times than you can count on one hand. A ride is $35 per person and you don’t have to charter the whole boat — a big plus for solo travelers or smaller groups.

Their classic Morgan cruising yacht, Island Girl, is graced with teak railings and an oversized bimini for shade. Watch the sky streak electric pink and orange from the middle of the Chesapeake Bay’s vastness. Add to this a couple of Waterman’s jumbo lump crab cakes and a beer, and you have the perfect end to a day on the Bay.

Plan Your Trip

Rock Hall is in the Goldilocks range for a weekend trip that feels far away, but doesn’t require an eight-hour flight. It’s a three-hour drive from New York City and a two-hour drive from Washington, D.C., Baltimore, and Philadelphia.

Explore On Land

For a stroll around Main Street, park in the gravel lot next to Rock Hall Village, a collection of brightly painted storefront shanties. It’s right next to the town’s only stoplight, the pared-down red and yellow kind. There are crafters and treat purveyors on this charming town green, including the best ice cream in town at Get The Scoop. Grab a cone and keep walking or eat your sundae at a picnic table on the nearby gazebo.

Along Main Street, you’ll likely pass a few garden club members tending to potted begonias, white curls poking out from underneath their sun hats. You might see Dave the mason drive by in his pickup truck, his chocolate lab grinning out the passenger side window, smelling the world fly by. If you smile and wave at anybody in town, they’ll smile and wave back, and maybe even strike up a conversation.

As you poke around the petite Main Street district, you’ll pass businesses like Smilin’ Jake’s Apparel, Chester River Kayak Adventures, The Hickory Stick Unique Boutique, Village Quilting, Java Rock Cafe, and The Mainstay, a love letter to jazz and live music. Throughout the year, they bring in bands and musicians from across Kent County, the USA, and the world. Thousands of autographs cover the walls, a visual history of the jazz, swing, bluegrass, bossa nova, and others who have played there over the decades.

Over the course of the third weekend of August every year, Kent County celebrates African American heritage at the Legacy Day Festival. Held at Wilmer Park on Chestertown’s beautiful waterfront, there's live music, vendors, and activities. The festival pays homage to Charles Graves, founder of Chestertown’s iconic, bygone Uptown Club, which — in a segregated Maryland of the '50s, '60s, and '70s — created a comfortable and safe space for African American residents to hear and see gifted entertainers like Etta James, Ray Charles, and James Brown.

You can also take a self-guided tour of African American history along the National Chesapeake Scenic Byway in Kent County. The Historical Society of Kent County offers paperless versions of architectural and cultural walking tours that you can do in any order, at any time.

Later, you can take a walk or bike ride down the final miles of Route 20 before it ends at the Chesapeake Bay. Osprey with their bandit masks nest atop tall poles crowned with wide, wooden platforms. Clusters of boat masts pierce the horizon. Ask at Haven Harbour for the key to the Waterman's Museum, its cottage guarded by a life-size, wooden waterman statue. The pathways around the building and grounds are paved with layers of white oyster shells.

Stay Somewhere Charming

Rock Hall is brimming with picturesque accommodations, all locally owned. Among the bed and breakfasts, marina hotels, motels, campgrounds, and Airbnbs, my favorites are the Inn at Haven Harbour, Osprey Point, and the Inn at Huntingfield Creek. Each has its own signature decor, thoughtful amenities, like complimentary bicycles or homemade salted chocolate chip cookies, and welcome pets if you like to travel with your furry companion. At any of these exceptional hotels you’ll have a beautiful place to unwind and crickets to serenade you to sleep.

Eat and Drink Well

Ford’s Seafood is a down-home diner where you can get the best bushel of steamed crabs around, a generous crab cake platter, and classic diner fare. In addition, they sell homemade cakes (whole or slices), such as carrot cake smothered in cream cheese frosting and my favorite, classic yellow cake with thick chocolate frosting.

Waterman’s Crab House offers award-winning food and water views at its prime location right on the harbor. Indoor dining is complemented by an expansive waterside deck for outdoor dining and grooving to live bands that play on the weekends. The menu includes ample seafood plates like the Broiled Rock Hall Combo (crab cake, shrimp, scallops, flounder, and two sides), but also BBQ ribs, tacos, and burgers. Later, at the dockside bar, order a peach sangria, Creamsicle Crush, or other summery drink.

At the corner of East Sharp Street and Main, you can sit outside Java Rock enjoying great coffee, sandwiches, and baked goods while listening for the church bells that chime on the hour.

Located in Chestertown, one town over from Rock Hall, Chester River Wine & Cheese Co. carries various local delights, like wine from Crow Hill Vineyard & Winery and Langenfelder Farm sausage. They also sell a beautifully curated panoply of liquor, olive oil, cheese, and other delectables. If you call 24 hours ahead, the cheesemongers will create a custom charcuterie board just for you.

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