Cyclists ride over a covered bridge in Kent, Connecticut

I Took a Bike Tour Through New York's Hudson Valley — Here's Where I Found 'Farm-to-glass' Whiskey and the Best Meals

On a cycling vacation through upstate New York and the Connecticut countryside, discover a whole new side of the Hudson Valley you think you know.

When I think "bike tours," I tend to imagine winding my way up Tuscan hills or pedaling through sunflower fields in Provence, sharing the roads with grizzled farmers in ancient Fiats and Citröens. But as the pandemic shifted the attention of many travelers to overlooked destinations in their own backyards, so too did it force tour operators to get creative. Last year, DuVine, an international cycling company, unveiled a tour of the Hudson Valley.

The prospect didn't exactly thrill me. As a longtime resident of New York City who has spent countless weekends pawing through antiques, raiding farm stands, and agonizing over that perpetual question — Could I live here? — I thought I'd essentially checked the Hudson Valley box. That said, I am an avid cyclist — and a veteran of many two-wheeled holidays — so any bike trip pretty much has me at "bike." Add some of upstate's finest farm-to-table food (and, as I would find out, "field-to-glass" whiskey), a home base at the cozy lodge Troutbeck (; doubles from $445), and the general fellowship of the people who typically choose to take bike tours, and, well, I could hardly say no.

The entrance to Troutbeck Hotel in New York
Once a retreat for New England’s literary elite, Troutbeck is now a boutique hotel, renovated in 2017 by Alexandra Champalimaud. Gwen Kidera/DuVine Cycling + Adventure Co.

On a simmering summer morning, I arrived solo to join a group of five couples assembled on the lawn at the culturally significant Troutbeck — over the last two centuries, guests have included Henry David Thoreau, Theodore Roosevelt, and Thurgood Marshall. The hotel occupies a 250-acre stretch in Amenia, New York, a hamlet near the border with Connecticut. My fellow cyclists had come farther than I had, hailing from Maryland, Virginia, Georgia, and even Mexico. One couple had e-bikes, the great equalizers — despite being in their 70s, they had no trouble matching the most energetic riders. We were led on the road by our guide, Ross Eustis, a New Yorker who'd gone to boarding school in the area; for him, passing a rival school where he'd played baseball was a literal trip down memory lane.

Just as the first motorists had the lobbying efforts of 19th-century cyclists to thank for the good roads they drove on, the contemporary cyclist can often give thanks to the railroad industry for creating some of the country's best biking infrastructure. The 26-mile Harlem Valley Rail Trail — which runs from Wassaic to Copake Falls and can be picked up near Troutbeck — featured often in our daily cycling plan. The trail provided a level, shaded, and traffic-free artery to places like Millerton, a tiny town that punches above its weight, with artisanal tea producer Harney & Sons (; the Edward Hopperesque Oakhurst Diner (; entrées $13–$25); coffee roaster Irving Farm (, where we stopped to refuel; and Westerlind (, a sort of hipster Woolworths.

When not on the rail trail, we traversed green and rolling back roads, crisscrossing the state border, past fields of thigh-high corn, gushing waterfalls, and tidy Dutch-style houses. We took refuge from the heat at places like McEnroe Organic Farm (, which has its own market and dining operation, and quenched our collective thirst with tastings of Kings Highway Fine Cider (, a zero-added-sugar drink produced by onetime journalist Tyler Graham, who started out making cider in his Brooklyn apartment.

A group of cyclists takes a lunch break at Kings Highway Fine Cider
A lunch stop at Kings Highway Fine Cider, in Millerton, New York. Gwen Kidera/DuVine Cycling + Adventure Co.

One afternoon we were joined by chef Gabe McMackin, an enthusiastic cyclist and former Brooklynite who closed his Michelin-starred restaurant, the Finch, in 2020; now he helms the food and beverage program at Troutbeck. He pointed out secret swimming holes and favorite pizza spots — like the Lantern Inn (; entrées $15–$20), in Wassaic. When he suddenly realized his own dinner service was looming, I agreed to bike back with him. After riding at a blistering pace, I collapsed in a hammock. He headed straight to the kitchen. But our group's meal that night was actually at Serevan (; entrées $32–$38), a regional staple founded by chef Serge Madikians, a self-described "Armenian from Iran" whose exquisite menu includes saffron-infused spaetzle, rack of lamb with herbed labne, and eggplant stew. Madikians is also a pilot; he's been known to ferry fresh seafood from Cape Cod in time for dinner.

The next day, the remnants of Tropical Storm Elsa began to whip through the valley, and we rode past power crews repairing downed lines. After a lunch stop — we stayed mostly dry under the porch roof of a delicatessen — we climbed into the support van for the short drive to Hillrock Estate Distillery (, which is housed in a home built by a Revolutionary War captain.

Hillrock was originally overseen by legendary distiller David Pickerell (he helped bring Maker's Mark to prominence) and still practices "floor malting" — laying out the barley in a Zen-garden-like spiral on a cold stone floor to let it germinate. My group retreated to a cozy room where five whiskeys were arrayed in front of each of us. After tasting fiery rye, smoky and sinuous single malt, and oaky-sweet bourbon, a few of us elected to return to Troutbeck by bike. There was a consistent drizzle, but we were warm, and there were still more country roads to be explored.

A version of this story first appeared in the June 2022 issue of Travel + Leisure under the headline Back in the Saddle.

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