Take the train from New York City up to Wassaic or drive directly to Troutbeck, our home for the next three nights. The guest list of this historic country retreat reads like a roster of great American authors⁠—including Twain, Thoreau, and Emerson—but feels appropriately modern, and succeeds at balancing a sense of place with all the creature comforts. We’ll get fitted to our bikes then head out for a first ride into the New York countryside. Lakes, forests, and dreamy pastures dot the route to Millerton, a sleepy little town experiencing a hip revival that’s earned it the nickname “Williamsburg on the Hudson.” Stop at a local organic farm stand for a casual lunch paired with a tasting of the best local ciders, then bike back to Troutbeck on the rail trail. Tonight we kick things off with a farm-to-table dinner hosted by the hotel’s award-winning chef.

Accomplished: 19 miles / 30 km, elevation gain: 731 feet / 255 meters Longer Option: 31 miles / 50 km, elevation gain: 1,801 feet / 549 meters

This morning we pedal out of Troutbeck, across the Appalachian Trail, and into Connecticut’s Housatonic River Valley. Follow the banks of the river to one of the state’s three remaining covered bridges, built in 1842. After, slip back across the New York border where our friend, a local chef, welcomes us with a home-cooked lunch at an organic farm. This afternoon we’ll ride through the fertile farmlands of the Tenmile River Valley, passing quaint towns like Dover Plains and Wassaic, home to a bustling art community. Back at Troutbeck, enjoy a cocktail by the pool with time to relax before dinner at our favorite local eatery.

Accomplished: 39 miles / 63 km, elevation gain: 1,906 feet / 581 meters Shorter Option: 19 miles / 30 km, elevation gain: 790 feet / 241 meters

Today we ride north, stopping at the best local coffee shop and roaster for a truly perfect cup. Fueled up, we’ll bike to a farm that specializes in growing a variety of greens—the perfect place to pick up tips on crafting a gorgeous salad. Our lunch is both farm-to-table and field-to-glass, since we’ll be enjoying our fresh-picked fare at a unique distillery that uses estate-grown grains. The Hudson Valley was once the breadbasket (and therefore also the “liquor basket”) of the young nation, where hundreds of small distilleries transformed their crops into grain alcohol. The distillery shares how it revived this tradition during a tour and lunchtime tasting of their whiskeys and bourbons. Ride or transfer back to the hotel, where tonight we’ll toast at a private dinner on Troutbeck’s estate.

Accomplished: 25 miles / 40 km, elevation gain: 1,171 feet / 357 meters

Longer Option: 48 miles / 78 km, elevation gain: 2,398 feet / 731 meters

No foodie can leave this part of the country without a meal at Arethusa Farms. In 1999, the current owners revitalized this 19th-century dairy farm and launched one of the nation’s most celebrated farm-to-table restaurants. The ride to Arethusa takes us over another picture-perfect covered bridge in West Cornwall and along the leafy lanes of this quiet corner of Connecticut. After a memorable lunch at award-winning Arethusa, choose to transfer or bike back to Troutbeck and say “see you later” to the Hudson Valley. For those taking the train, your guides will bid you farewell at the Wassaic station.

Accomplished: 26 miles / 42 km, elevation gain: 2,207 feet / 673 meters

Longer Option: 57 miles / 92 km, elevation gain: 3,775 feet / 1,151 meters