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

What’s Included in the Cost of Your Trip?


3 nights lodging
All breakfasts and 1 dinner
Luggage transfers
Detailed GPS instructions and maps
Personal meet & greet with our local Area Manager
Area Manager available throughout the tour



You can start any date between May and October.
Custom trips also available and can start any day. Call or email for details.


4 days / 3 nights








Land Cost:
US $1,950 pp
Single supplement: US $475

Bike Rentals

Hybrid or Racing Bikes: US$180

E-Bikes: US$240

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.  

Please note: Final itinerary is subject to revision; any changes made are done so in an attempt to provide the best possible trip given route conditions and available services. Due to the nature of our business and exchange rates, prices are subject to change. All prices quoted are U.S. dollars but we gladly accept payment in Canadian dollars also. If you have any questions before making your reservation, please contact us.
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.


Day 1


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.

Ride distance: 20mi (32km); elevation gain 1,000’ (340m).


Day 2

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.

Ride distance: 36mi (60km); elevation gain 2,700’ (900m).


Day 3


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.

Ride distance: 42mi (72km); elevation gain 2,700’ (910m).


Day 4


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 2 story barn. Enjoy lunch and then shuttle back to the Troutbeck to depart.

Ride distance: 30mi (50km); elevation gain 1,950’ (650m).


Troutbeck, Amenia

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.

Trip starting at
USD $1,950