Dark gray clouds scudded low overhead, pewter waves slapped Windbird’s hull as it heeled in a gust, and a fine, cold mist obscured the low black line on the horizon that defined our island destination, now 7 miles away. Given the sullen weather, you wouldn’t know it was July 5 if not for the steady stream of post-holiday vessel traffic headed in the opposite direction.
“Intensely variable conditions are just part of the bargain for any New England cruise,” I mused, “no matter the season.” As we rounded the Tuckernuck Shoal Buoy, its haunting discordant gongs echoing across the chop, I tightened Windbird’s sheets and hardened our course toward the harbor entrance. Our sturdy sailboat dug in its heels and surged windward with renewed vigor, spray flying over the bow and smacking our dodger. I smiled. The salty weather reminded me a lot of our last visit to Nantucket, Massachusetts, eight years ago and just before a major storm, in a very different sort of traveling machine.
In 2012, Dawn and I were living in Minnesota and had not yet purchased our Piper Pacer, but we had the use of several friends’ airplanes scattered around the country. One of these was a beautiful 1984 Piper Warrior, kept in a scenic little Chester, Connecticut, hangar. My former student Johnny Gioelli (“Rock Star Johnny,” November 2014) had put me on his insurance and told me to come fly whenever I liked, an offer I had taken him up on several times. Dawn originally wanted to go to New England at the height of leaf-peeping season, but our work schedules didn’t line up until the last weekend in October.
With the fall colors past peak, I planned a flight east along the coastline to Nantucket. As the appointed weekend approached, the airline loads to Hartford, Connecticut, and the flying weather from Chester to Nantucket both looked quite good, but there was one major complication: The late-season hurricane the media had deemed Superstorm Sandy for its record-breaking 900-mile diameter was churning its way up the Atlantic seaboard on a collision course with the northeastern states.
In retrospect, knowing the devastation that Sandy wrought—and with the experience of owning my own airplane and perhaps a sailor’s increased respect for the weather—I’m not sure that a cross-country flight just ahead of a major hurricane was the brightest idea I’ve ever had. It certainly had the potential to put my friend’s generously offered airplane in harm’s way. But at the time, it seemed all right; the storm’s stately progress northward was pretty well-established, landfall wasn’t expected until Monday evening, and the forecast for our return on Sunday morning looked OK, if a bit windy. I reasoned that if the forecast changed, we could just fly back on Saturday night.
We flew my airline into Hartford on Friday night, and Saturday dawned clear and bright and warm—a beautiful fall day in New England. We took off from Chester, climbed out over the Connecticut River and the historic seaport of Essex, then turned east along the rocky coastline. Long Island Sound sparkled in the morning sunlight, and only the appearance of long swells from the south after we passed Fisher’s Island signaled the approaching storm. We circled over Newport, Rhode Island’s usually busy harbor; only a few tall mega-yachts remained at their moorings, most other vessels congregating around the shipyard’s busy lifts.
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At Buzzards Bay, Massachusetts, we detoured northeastward to Provincetown, at the far end of Cape Cod, and then flew down the cape’s marshy eastern shoreline to Monomoy Island before climbing for the cold-water crossing to Nantucket. Descending over the historic harbor, Nantucket appeared to be the absolute end of the world, with slate-gray ocean stretching for thousands of miles from northeast through southwest. From these waters, the island made its fortune and fame; from this isolation, the island gained its modern status as an exclusive hideaway.
High, wispy clouds had started to cover the sun by the time we landed in a stiffening crosswind at Nantucket Memorial Airport, and the day took on a distinctly cooler feel during the short cab ride to Nantucket’s main town—known simply and rather charmingly as “town” (though there are several other villages on the island). The last remaining leaves gave up the ghost and swirled madly down cobblestoned lanes, and several storefronts on Main Street were boarding up—as much for the winter as for the storm.
The entire island of Nantucket is designated as a National Historic Landmark district, and downtown has a particularly handsome collection of weathered clapboard structures from the mid-to-late 1700s and early 1800s. Among these was our bed-and-breakfast. We were the only guests, possibly the last of the season. After checking in, Dawn and I wandered through the photogenic but largely empty town, snapping photos. I hoped to visit the whaling museum, but it was closed. Instead, we walked out to the Coast Guard station and lighthouse at Brant Point and watched fishermen in the harbor working feverishly to haul their boats before the storm.
Late in the afternoon, having rechecked the forecast and deciding it was safe to spend the night, we went for drinks at Cap’n Tobey’s Chowder House, a Nantucket institution on Straight Wharf since 1954. It was my kind of place, an atmospheric dive with a lot of nautical and fishing decor and cheap beer on tap. It also happened to be their last day in business, having sold the building for over $3 million to a venture capitalist from Boston, so they were throwing one last big hurrah—a fare-thee-well/hurricane party with weirdly mixed vibes of wistful nostalgia and pre-apocalyptic hedonism. The place was heaving with locals, and we stayed late. “Look around you, kid,” extolled the red-faced lobsterman seated next to me with a much younger woman in his lap. “Here goes the last bit of the old island. There will be a Gucci store here by springtime.”
The next morning, the deterioration of the weather was startling, and I wondered if I had made a mistake staying overnight. Freezing wind intermittently laced with stinging raindrops positively whistled through town, and dark, angry clouds wheeled rapidly overhead. These were, I realized, the outer bands of the storm, nearly 36 hours before landfall. I checked the metar: overcast at 2,000 feet, almost 30 knots of wind, albeit straight down the runway. Yes, it was time to go. When we got to the airport, the ramp was shockingly empty; only a few large bizjets remained, and their crews were busily preparing to get out of Dodge.
I held my breath while turning the ignition key, and thankfully, the faithful Lycoming turned over rapidly and fired up on the third blade. Soon, we were bumping along at 1,000 feet with a mighty tailwind across Martha’s Vineyard, the Elizabeth Islands and the Rhode Island coastline, dodging bands of rain. I’d always been fascinated by hurricane hunters, and now I was one—though the humble Cherokee seemed a less appropriate choice than Lockheed’s beefy P-3 Orion. I didn’t breathe easy until Johnny’s Warrior was tucked safely inside his hangar. We made tracks for Hartford and got out on the next flight, and the following day Hurricane Sandy wreaked havoc all across the region. Later that week, I captained one of the first flights into New York’s LaGuardia Airport after it reopened, and there was still seaweed on the ramp.
Eight years later, COVID-19 was the storm on the horizon, but on July 5, it didn’t seem to be hurting Nantucket too badly; the place was chockablock with holiday tourists. We shoehorned Windbird into the crowded anchorage between mega-yachts 10 times our tonnage, masked up and took the dinghy into town. It was scarcely recognizable as the same place we had visited in 2012. Many buildings had been spruced up, there were more high-end boutiques, restaurants had seemed to proliferate (and, with the pandemic, had spilled out into the cobblestone streets), and prices were sky-high. I checked the old site of Cap’n Tobey’s; it wasn’t a Gucci store, but there was a nice restaurant with $10 beer on tap. We contented ourselves exploring Nantucket’s world-class (and free) beaches and picturesque historic villages.
A few days later, the wind had clocked completely round (with multiple weather changes daily), and we had a nice downwind spinnaker sail to Martha’s Vineyard. The Vineyard is perhaps most famous, in aviation circles, for Katama Airpark, a multirunway grass strip that is a popular seaside fly-in destination complete with its own $500-hamburger joint, the Right Fork Diner. Hopefully we too will fly to Katama someday, when we have another airplane of our own. It’s been interesting to visit places by sea that we’ve seen by air and vice versa. That said, I have decided to institute a firm “no hurricanes” policy for any aircraft smaller than a P-3 and for all vessels lighter than the USS Nimitz.
This story appeared in the September 2020 issue of Flying Magazine