Exploring Hudson Valley by Bike: Discovering Farm-to-Glass Whiskey and Top Culinary Delights

Exploring the Hudson Valley on Two Wheels

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 farmers in vintage cars. However, as the pandemic shifted travelers’ attention to overlooked destinations in their own backyards, tour operators have had to get creative. Last year, DuVine, an international cycling company, unveiled a tour of the Hudson Valley.

Staying at Troutbeck Hotel

As a longtime resident of New York City who has spent countless weekends exploring antiques and local markets, I thought I’d checked off the Hudson Valley. Nonetheless, as an avid cyclist and a veteran of many two-wheeled vacations, any bike trip had me at “bike.” The allure of upstate’s finest farm-to-table food, a cozy lodge at Troutbeck (troutbeck.com; doubles from $445), and the camaraderie typical of bike tours made it hard to resist.

Adventuring on the Rail Trail

On a 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, notable guests have included Henry David Thoreau and Theodore Roosevelt. The hotel nestles on a 250-acre stretch in Amenia, New York, near the Connecticut border. My fellow cyclists hailed from Maryland, Virginia, Georgia, and even Mexico. One couple, equipped with e-bikes, demonstrated that age doesn’t hinder enthusiasm for biking.

Our guide, Ross Eustis, a New Yorker familiar with the area, led us along the 26-mile Harlem Valley Rail Trail—an invaluable biking resource. The trail provided a flat, wooded, and traffic-free route to charming spots like Millerton, home to artisanal tea producer Harney & Sons (harney.com), and the Edward Hopper-inspired Oakhurst Diner (oakhurst-diner.com; entrées $13–$25), renowned for its local flavor.

Culinary Experiences Along the Route

When not biking the rail trail, we rode through picturesque back roads, past fields of corn and gushing waterfalls, finding solace at places like McEnroe Organic Farm (mcenroeorganicfarm.com). We quenched our thirst with tastings from Kings Highway Fine Cider (cider.nyc), crafted by Tyler Graham, a former journalist turned cider-maker.

On one notable afternoon, chef Gabe McMackin shared culinary insights. After his Michelin-starred restaurant closed during the pandemic, he became involved with the culinary program at Troutbeck, enthusiastically guiding us to favorite local spots, such as the Lantern Inn (wassaiclanterninn.com; entrées $15–$20). Our dinner that evening was at Serevan (serevan.com; entrées $32–$38), offering a delightful blend of flavors, courtesy of chef Serge Madikians.

Visiting Hillrock Estate Distillery

The next day, as remnants of Tropical Storm Elsa swirled through the valley, we paused for lunch under a deli’s porch before heading to Hillrock Estate Distillery (hillrockdistillery.com), where a Revolutionary War captain once built a home. Hillrock remains committed to traditional distilling techniques.

In a cozy room, we sampled an array of five whiskies, each showcasing distinct flavors. A few of us opted to bike back to Troutbeck despite the drizzle, proving that there’s always more to explore in the beautiful countryside.

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