Travel & Leisure recently named the Hudson Valley as one of the most exciting places to travel in 2021. With its thriving locavore movement of boutique farms and orchards, charming villages, historic properties and quiet rural roads, the appeal is evident. This 4 day, 3 night escape provides an itinerary from the wonderful Troutbeck, just outside of Amenia, NY.
Troutbeck, Leedsville Road, Amenia, New York, USA
Day 1+2+3+4
| Start any date between May 1 and Oct 31. |
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| Custom trips are also available and can start any date, call or email for details. |
Total Days
Arrive/Depart
Activity LevelModerate
TerrainModerate
CostLuxe Accommodation: US $2,120
Single Supplement: US $540
Bike Rentals
Hybrid Bikes: US $180
Racing Bikes: US $240
E-Bikes*: US $280
*E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.
Getting There
You can easily reach Troutbeck in Dutchess County by train to Wassaic Station. We will pick you up on arrival (10:15 am), whisk you to the Troutbeck and provide bikes so you can head out cycling! This region has plenty of quiet roads, covered bridges, enchanting villages and cool barns to discover. This is a land of farm-to-table restaurants, craft distilleries and more.
Millerton
After arriving to the hotel, settle in and then head out cycling. The first day’s route follows the flat & paved Harlem Valley Rail Trail to the village of Millerton. Voted one of America’s Favorite Small Towns, stop in at Irving Farm for a fresh roasted coffee and then visit any one of the many art galleries and antique stores. On the return route, stop in at an organic farm market and sample organically raised fruit and vegetables, or some of the owners pickled, baked, jammed, stewed and simmered bounty. Arriving back to the hotel, relax and enjoy dinner in the delightful dining room.
Distance: 20 mi (32 km); elevation gain: 1,000 ft (340 m)
Housatonic Valley
Today, ride across the border into Connecticut and the Housatonic River Valley. Near a trailhead for the Appalachian Trail, cross a historic covered bridge built in 1842 and now a National Historic Monument. Pass historic barns on quiet secondary roads to Kent, a charming village with great restaurant options for lunch before riding back to Troutbeck. You’ll probably want to dine out on at least one of the nights you are here and we have just the place to recommend, in nearby Amenia.
Distance: 36 mi (60 km); elevation gain: 2,700 ft (900 m)
Troutbeck
Ride north today discovering more of the region. In the early 1800’s, New York produced more than half the nation’s barley and rye and the Hudson Valley was the country’s breadbasket. With abundant high quality grain, local craft spirits flourished and over 1000 farm distilleries produced whiskey and gin reflecting the unique terroir of the region. In the 1930’s, Prohibition forced these distilleries to shut their doors but there has been a resurgence in this craft. Enjoy a behind-the-scene tour of one of the premier distilleries and taste award-winning whiskeys, or save that for when you are back to the hotel.
Distance: 42 mi (72 km); elevation gain: 2,700 ft (910 m)
Rhinebeck
There is time for one last ride, to the village of Rhinebeck, settled by the Dutch in the 1680’s. Peek in the Beekman Arms which has operated continuously since 1766, retaining much of its colonial charm and character. Check out the Antique Market, a multi-dealer antique emporium that is located behind the hotel in a classic two-story barn. Enjoy lunch and then shuttle back to the Troutbeck to depart.
Distance: 30 mi (50 km); elevation gain: 1,950 ft (650 m)
This property is a historic country inn that began as a private estate built in 1765 by a prominent New York family who played host to Mark Twain, Ralph Waldo Emmerson, and Henry David Thoreau, among others. The property sits on 250 acres with comfortable guest rooms, library, stunning outdoor swimming pool, two US Open-surface tennis courts, formal gardens and an impressive farm-to-table restaurant.
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