It was a difficult choice. My sister-in-law and her spouse invited us to join them on Calypso, their Mainship 390, for a cruise anywhere along the Great Loop—a circumnavigation of the waterways of the Eastern and Central United States.
“How about Florida?” my husband, Frank, asked, thinking we could join his sister at the beginning of her yearlong adventure. “Or the Dismal Swamp?” But that sounded more mysterious—and hot—than this Seattle-based sailor could handle.
“The Chesapeake would be interesting,” Frank suggested. “We could try the blue crab.”
After considering the varied destinations of the Loop, we decided on the Hudson River Valley segment. As West Coast sailors, we knew that cruising up an Eastern river in a trawler would be a novel experience for us. As a historian, I wanted to see the waterway that had inspired so many artists and writers throughout the centuries. And could there be a more exciting departure point than New York City?
The River
Calypso picked us up at a busy dock in Manhattan on a sunny day in June. By that time, my in-laws Pat and Steve Stanley, who started the Great Loop on the Gulf Coast, had already logged more than a thousand miles. New York Harbor was bustling with tankers, tugs, ferries, sailboats and other trawlers as we boarded the boat for the first time.
Our time at the Chelsea Piers dock was brief, and Pat invited us to the flybridge to view the scene as Steve navigated through the remnants of an old wharf. The Statue of Liberty, always a thrill to view from the water, was visible in the distance as we turned upriver, gliding past what might be the world’s most impressive city skyline. When we cruised under the George Washington Bridge, the skyscrapers and boat traffic began to recede, and the shoreline quickly gave rise to the steep cliffs of the Palisades.
The noise of the city was quickly forgotten as we drifted past the places of Hudson River lore: Spuyten Duyvil (a “spouting devil” of tidal currents), Riverdale, Hastings-on-Hudson, Ardsley-on-Hudson, Sleepy Hollow, Scarborough and others. While we had traveled just a few miles north of Manhattan, a different world lay before us. This is a riverscape lush with deciduous trees and dense foliage covering low-lying hills, still looking very much like the paintings of Thomas Cole and Asher Brown Durand of the Hudson River School—a movement that brought visibility to American art in the 19th century. You could almost see Rip Van Winkle or Ichabod Crane on the leafy shore.
A few miles upriver, we encountered another famous structure: the Tappan Zee Bridge. This massive cable-stayed structure, which replaced an older version and is officially named the Governor Mario M. Cuomo Bridge, opened in 2017 and reveals how the new blends with the old along the river. Soon after making way under the bridge, the historic Tarrytown Lighthouse, a conical tower erected in the 1880s, appeared almost immediately on the east bank, in the community of Sleepy Hollow.
While vessel traffic had decreased since we left Manhattan, Calypso was rarely alone. The Hudson is a river of boats, including commercial and recreational craft, large and small. At Tarrytown, we passed multiple barges and tugs, while kayaks poked along the shoreline. In front of us, sailboats tacked across the river in light air. Other Loopers occasionally cruised by in their trawlers, which Pat identified on NEBO, the boat-logging app used by members of the America’s Great Loop Cruisers’ Association. Pat and Steve keep a notebook of boat cards from other loopers they meet, which they consulted each time an association boat showed up on the app. An estimated 400 vessels were doing the Loop in 2022, and these boaters form a tightknit community.
The Boat
Our first overnight stop was Half Moon Bay Marina, an association sponsor. Located next to Croton Point Park and the river walkway, it is an idyllic spot. As we docked, Steve engaged the bow thrusters and we eased into our slip—a perfect landing.
Our first activity was a toast to Neptune to celebrate our safe passage. It is a family tradition that Pat and Steve have shared with us on many cruises. The flybridge offered a view of the sunset, and we watched herons gliding over the bay between the sailboats at anchor, while Steve serenaded us on his trumpet.
Frank and I were now free to become more acquainted with the features of Calypso. The Mainship 390 has a fuel-efficient, single diesel engine, housed in a room with sufficient space to perform checks and maintenance with ease. The salon and galley are spacious, with ample stowage. There are two staterooms, allowing for extra stowage and a comfortable place for guests on bunks. When I asked Pat about the size of the area between the beds, she explained that on Calypso, length is relative to the number of wine boxes laid side-by-side. “I think the guest beds are two wine boxes apart,” she informed us.
Pat and Steve purchased their Mainship 390 specifically to do the Loop, and they quickly learned why it has been the most popular choice for loopers “crossing their wakes” in recent years.
“The flybridge is wonderful,” she said. “We can drive from the upper helm and have a great view of the waterway, traffic and obstructions. We also like having the lower helm during heavy rains and/or rocky conditions. There is less swing from the lower deck, and the windshield wipers help with visibility.”
The flybridge was my favorite spot, too. When it came time to sleep, Frank and I brought our blankets up there, where we could feel the cool breeze and the flow of the river, while listening to bird calls and crickets. We are sailors after all, used to spending time in the open air.
The People
Our next stop was the Cortlandt Yacht Club, another America’s Great Loop Cruisers’ Association sponsor, located next to Montrose Point State Forest. Frank and I had never encountered friendlier people at a marina. After helping us dock, they offered detailed advice about exploring the nearby lakes and villages on foot.
Convinced, we went for a walk to historic Verplanck, where signs identified sites from the Revolutionary War era. The past echoes strongly here. This is the place George Washington encamped with the Continental Army in preparation for crossing the Hudson at Kings Ferry. It is also where Washington presented medals to the patriots who captured Major John André, a British spy associated with Benedict Arnold.
That afternoon, our dock neighbor suggested that we go to dinner in town. Learning that we had no car, he offered to drive us to a restaurant called Fat Sal’s, providing us his personal number for our ride home. Our meal, served outdoors in the June air, was a highlight of the trip, made possible by the generosity of Cortlandt Yacht Club members, who brought us there and back.
This marina is well protected from the fierce winds that can blast through the Hudson River Valley. The lack of breeze, however, meant that our night on the flybridge was plagued with mosquitos.
As we prepared to leave the dock, our dockmate assured us that the best of our trip was just ahead. “It’s my favorite part of the Hudson,” he said. “The scenery is really something.”
He was right. As we wound our way along the bends in the river, the Hudson Highlands came into view, partly shrouded in mist. This is what Washington Irving called “the fairy region of the Hudson.” It inspired some of his enchanted forest stories. Up ahead, the historic Bear Mountain Bridge, completed in 1924, spanned the river. “That’s the part of the Appalachian Trail,” Frank pointed out as Calypso passed under the structure.
Soon, West Point appeared on the west bank. Fellow Loopers took our photo as we stopped to admire the Tudor revival and federal-style architecture while reflecting on the role of the U.S. Military Academy in American history. Farther up the river, Calypso would encounter the eerie Bannerman Castle and several historical lighthouses.
At the end of our trip, Calypso dropped us off at Cold Spring. A passerby—not a boater—noticed me searching my phone for directions to the train station. “I’ll walk you there,” he offered. Guiding us through the streets of this charming hamlet, he mentioned historical points of interest. It turns out George Washington drank there (we assumed that meant water from the spring).
Soon, Frank and I arrived at the Metro-North rail line to take us back to New York City and the airport, heartened by the warm reception we encountered on the Loop.
“We meet fantastic people who are likely to become lifelong friends along the way,” Pat told us of her experience, while also seeing “parts of the United States that we’ve never seen before.”
She and Steve consider our cruise through New York Harbor and up the Hudson River to be one of the high points of their trip. Kim Russo, director of the America’s Great Loop Cruisers’ Association, told us it was also her partner’s favorite cruising grounds during his first Great Loop.
Frank and I can see why. We vow to return, perhaps to do the rest of the trip in our own trawler.
This article was originally published in the March 2023 issue.
