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A visit to Smith Island, which is actually a group of islands 12 miles off the coast, begins with a boat ride. Period. The mostly marshy 3-mile-long, 5-mile-wide swath of terra-sorta-firma has no bridge connecting it to the mainland and no airport. One of the three villages is connected to the others only by water. And although you can catch a ferry to Smith Island from either Crisfield or Point Lookout, Maryland, the very best way to arrive is unquestionably on your own boat. Do so, and you'll learn that it isn't necessary to cruise across an ocean to have a cultural encounter unlike any found on the mainland of continental America. Throw in a pinch of culinary ingenuity, a dash of quirky history, and a heaping helping of raw nature, and you've found a cruising destination as unique as any on the face of the planet — despite being in the regional backyard of more than 10 million Americans.

The Voyage

Melissa and Lenny take a selfie break at Hooper Island light
On the cruise to Smith Island, Melissa and Lenny take a selfie
break at Hooper Island light.

At 8:30 a.m., my wife, Melissa, and I toss the lines off of our 22-foot Glacier Bay center-console in Edgewater, Maryland. We have the cooler packed with enough food for our dinners, as it's past Labor Day and the two restaurants in Ewell, the town where we'll be staying, have limited off-season hours. There's a 15-knot southeast breeze blowing that will make things a bit bumpy during our 58.9-nautical-mile journey, but only for parts of it. One of the unusual aspects of the Chesapeake is that due to its curvature and constantly changing shoreline, you can encounter completely different conditions while cruising through its different parts.

For many miles we enjoy partial shelter from the Eastern Shore and waves no bigger than a foot, but when the Choptank River opens up to the east, we're exposed to a much longer fetch. The waves build to 2 feet and stay that way, until 7 miles later we enter the lee of Taylor's Island. What was a fetch of up to 15 miles shrinks to 2, and the seas go from choppy to charming. Some 12 miles later we wave at Solomons Island as we pass the Patuxent River. Melissa and I have cruised there before and found Solomons wonderful, but you can get there in a car. Somehow, having the bow pointed to a boats-only destination makes places connected to asphalt arteries seem boring in comparison.

Smith Island Harbor at sunset

Ewell at sunset. The red building is Captain Mark's crab shanty and shedding operation.

The seas soon get rough again as the low-lying marsh islands of the Tangier Sound to our port do little to interrupt the breeze. But we can see Smith Island now, just east of the hulking American Mariner, a half-sunk liberty ship sitting on bottom in shallow water. Decades of target practice courtesy of the U.S. Air Force left the ship almost cut in two, but from this vantage point it appears to be one looming mass on the horizon. Soon after gazing at it, we pass between the rock jetties protecting the entrance to Ewell Harbor.

Nav Tips: Smith Island Entrance

The Big Thoroughfare channel leading from the western side of Smith Island to Ewell has two main sections. The first is very well marked and goes for about 0.9 nautical miles from the jetties to the No. 10 red day marker. At that marker, it makes a nearly 90-degree turn to starboard, then runs about a half-nautical mile to the harbor. This second stretch runs a straight course to the green 15 marker, but is relatively narrow, so navigating through it at slow speeds is recommended.

The channel has been dredged in recent years with an authorized depth of 7 feet MLLW (mean lower low water) and a width of 60 feet, according to the U.S. Army Corps of Engineers, and the lowest depth we observed while in the channel was 8 feet. Slips for boats up to 60 feet at the Smith Island Marina are also advertised to maintain 7 feet. Shore power and water are available, and the harbor is very sheltered.

Smith Island map

Aviary Arrival

There's no speed zone through the first leg of the channel, but we pull the throttles back anyway. It would be tragic to zoom past Swan Island, to our port, part of Martin National Wildlife Refuge. Comprising the northern half of Smith Island, this 4,548-acre refuge is home to a shockingly long list of waterfowl and birds ranging from green-wing teal to peregrine falcons. We're not dedicated bird-watchers, but the feathered fauna is impossible to overlook. Over the next 24 hours, we'll spot oyster catchers nesting just a few feet from the water, railbirds darting through the marsh, and ducks waddling through front yards. Osprey, herons, and egrets are ever-present from the moment we pass through the jetties until the moment we depart. And while fishing in Channel Point Gut, flock after flock of brown pelicans coast along the shoreline and pass so close overhead that we pause casting for fear of hitting one with a fishing lure.

Transporting oysters

Kaitlin Noelle transports oysters purchased from dredgers in Ewell to a shucking house in Crisfield, Maryland. (Photo: Jay Fleming)

We idle into the slip that comes with "The Pearl," a renovated waterman's house-turned-VRBO rental, tie off the lines, and begin loading gear into our golf cart. Here on Smith Island, golf carts are the main mode of transportation. The few paved roads are tight, there's only one gas station (which serves far more boats than cars), there are no traffic lights, and you could stroll from one end of town to the other in 15 minutes. Rhodes Point, the only other town connected by road, is a whopping 1.3-mile trek. On top of that, a constant salt breeze can pockmark the finest steel GM has ever fashioned in short order. So having a car here just doesn't make a heck of a lot of sense.

Colorful crab floats

Colorful crab floats hang on a fence. (Photo: Jay Fleming)

Checking out the town itself consists of several highlights. There's the Cultural Center and Museum, a small but well-designed and -maintained facility that has the aura of a rural welcome center. We end up in a 30-minute conversation with the center's director, greeter, historical muse, and head bottle-washer, Sandie. Then it's on to the Harbor Side Deli for lunch. While ordering a crab cake sandwich isn't legally mandated, it should be — Smith Island's main industry is crabbing, and the inhabitants have more than 400 years of ancestral knowledge dedicated to preparing the Chesapeake's most delectable crustacean. It's only after eating, however, that we stroll to what may be the island's premier culinary destination: Smith Island Bakery.

Accommodations & Eateries

If your boat doesn't have the accommodations for staying aboard at the marina, there are a few options similar to The Pearl available on VRBO (though not with slips). There are also a few bed & breakfast establishments, campsites, and slips with showers. Remember that even in-season most businesses close early, restaurants included. However, several islanders will make home-cooked meals for visitors and deliver them by golf cart; Captain Mark will even bring you steamed crabs. Contact information for businesses and services can be found by contacting the Smith Island Cultural Center and Museum.

Just Desserts

How to describe a Smith Island cake? Many words come to mind: incomparable, irresistible, delightful, and certainly delicious. But none of those do justice to a cake so good that Marylanders saw fit to declare it the official State Dessert. Epic — that's the word to best describe a genuine Smith Island cake.

Smith Island cake

Smith Island cake is a local delicacy and the state dessert of Maryland. 

The evolution of Smith Island cakes is poorly documented, but lore has it that a lack of reliable electricity (power lines didn't reach Smith Island until 1978) and using wood-fired ovens necessitated baking eight to 10 thin layers, rather than one or two thick ones, to make a full-sized cake. Others say that the cakes were originally baked with their many thin sheets because layering in the fudgy icing prevented the cake from going stale when the bakers, all wives of watermen, sent their husbands off to harvest oysters for days at a time. Whatever the reason, the multilayer copycats served in some mainland restaurants or ordered from shadowy corners of the dark web can't compare. (For the record, is the real deal.)

We choose chocolate peanut butter from the list of options, bemoan the fact that the "Cake Academy" classes are on hold due to COVID, and spend another 20 minutes intermittently praising and chatting with the flour-dusted woman who walked from the ovens to the counter when we arrived.

Golf-carting back to The Pearl should take two minutes, but we stop to chat so frequently it instead takes more like two hours. Island natives have a unique accent, developed over generations of isolated existence, which makes conversing with them all the more irresistible. While the linguistic twang is one thing, their "backwards talk" is another. In a way that makes sarcasm seem downright charming, islanders will say the exact opposite of what they mean to get a point across. Thus, "I like your boat" may well come out as "I don't think nothin' of your boat." Interestingly, however, the Islanders are well aware of how their linguistic peculiarities can confuse mainlanders. They tend to talk slowly and clearly among strangers, and you need to engage several locals at the same time before getting the full flavor of the conversational experience. That said, in a way there are no "strangers" on Smith Island. These people radiate hospitality and seem to want to get to know you every bit as much as you might want to get to know them.

Captain Mike explains crab shedding

Captain Mark explains the finer points of crab shedding to the author.

Hard crab shed its shell to become a soft crab

While visiting Captain Mark’s shanty, we watched firsthand as a hard crab shed its shell to become a soft crab.

As we travel this short road, we meet a man who appears to be somewhere between 90 and 100 years old, just in from running his trotline for crabs. He tells us about his day while grinning like a 10-year-old who's just filled his first bushel basket. We meet Captain Mark, who has a crab-shedding operation 50 yards from the main drag, and in his half-hour crab shanty tour we learn more about how, why, and when crabs go from hard to soft and back again than most people will learn in a lifetime — we even get to watch a crab molt before our eyes. We meet Patrick, who moved to Smith Island to live out his final months with a terminal cancer diagnosis, beat the odds, and discovered he had zero desire to return to the mainland. And we meet "the Doc," who is not only a doctor but also an oyster farmer. It comes out in conversation that Patrick and the Doc are both anglers. Would they like to join us for an evening fishing trip? Of course! Although the fishing is slow, the company is fabulous. Melissa catches the biggest fish, a speckled sea trout destined for the grill.

Melissa with trout catch

Fishing was slow on this trip, but Melissa caught a speckled sea trout fit for the grill. 

The next morning, we pull the boat past the "downtown" waterfront, which includes a marina with transient docks, the Bayside Inn, and the Harbor Side Deli, then tie up at the lone fuel dock. It takes 10 minutes to fill the fuel tanks, but we don't leave until half an hour later after enjoying a discussion with the proprietor about the high tides that, in these days of rising water, now creep up the roadway; about the pair of golden retrievers playing in the parking lot; the life of watermen; and how the goats across the creek predict the weather.

Wait, What?

Yes, the goats. In another quirk of history, the spit of land directly across from Ewell's channel is inhabited by feral goats. They're playing hard to get at the moment and hiding in the scrub brush, but we're told that when they come out to sun themselves on the beach, you know "no blow is a-comin'."

Kicking back in Jack and Pickles

Kicking back in Jack and Pickles, one of the few businesses on the island that stays open after sunset. 

Could this place really exist a mere 58.9 miles from home? If we'd gone 589 or 5,890 miles, the experience would have been no less unique and no less enjoyable. That's not to say that everything here is idyllic. The mosquitos on Smith Island are hungry. Even in season the restaurants close early, and nightlife is limited to a single establishment, Jack and Pickles, an energetic but small arcade. You certainly won't find the standard-issue tourist town tchotchke shops, pubs, or amusement parks. There's no flash, no sizzle.

More importantly, there also is no asphalt artery that will bring you here. Cruise to Smith Island and you'll find that discovering the heart of a distant culture is just a boat ride — and then a golf cart ride — away.

An Island Out Of Time

Published in 1996, "An Island Out of Time: A Memoir of Smith Island in the Chesapeake," has become the classic way to get to know Smith Island without actually being there. Author Tom Horton spent three years living on the island with his family, immersed in its microculture and the inner workings of the community. The result is an intimate portrait of a deeply traditional community that lived much as their ancestors did 300 years before, attuned to the habits of blue crab, oyster, and waterfowl.

The much-lauded book also led to a half-hour Maryland Public Television documentary of the same name, narrated by Horton, which aired in 2019 and can be viewed on YouTube. $16.95 | or used booksellers.


Lenny Rudow

New Boats, Fishing & Electronics Editor, BoatUS Magazine

Top tech writer and accomplished sports fisherman, BoatUS Magazine Contributing Editor Lenny Rudow has written seven practical boating books, won 30 awards from Boating Writers International — many for his marine electronics articles – and two for excellence from the Outdoor Writers Association of America. He judges the NMMA Innovation Awards, and is Angler in Chief at FishTalk, his own Chesapeake-based publication. A great teacher and inspirational writer, Lenny hosts many of BoatUS Magazine’s very-popular how-to videos, which can be found on the BoatUS YouTube channel, or at