The Hudson Valley has long attracted prominent families from New York, who built mansions and estates among the farms and orchards. Former factory towns such as Beacon, Kingston and Hudson have been revitalized and new hotels, spas, & farm-to-table restaurants are taking advantage of the bounty of the region (and wines, craft brews and whiskies) to raise the bar for visitors seeking refined experiences in dining and sipping. Because of its rural nature, there are plenty of quiet roads, rail trails and signed bike routes to take advantage of where red barns and covered bridges await. Ready when you are.



Milton, New York, USA

Day 1+2


Rhinebeck, NY, USA

Day 3


Troutbeck, Leedsville Road, Amenia, New York, USA

Day 4+5+6

What’s Included in the Cost of Your Trip?


5 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.


6 days / 5 nights


Beacon / Troutbeck






Land Cost:
US $2,850 pp
Single supplement: US $750

Bike Rentals

Hybrid or Racing Bikes: US$240

E-Bikes: US$400

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.


Day 1

Marlboro & Milton

Arrive to Beacon mid-morning, where we meet you to provide your bikes and take your luggage. Ride out of town and cross the Hudson River on a bike lane before turning north along the river. Stop and visit Benmarl Winery, who lays claim to be the oldest vineyard in America. Have lunch in the delightful village of Marlboro. Late afternoon, pass through Milton and then just before the hotel, pop into Locust Grove farm, or the brewery next door for a wee pint. Settle into the Buttermilk Falls Inn & Spa, set on a 75-acre estate. Enjoy dinner at Henry’s at the Farm.

Ride distance: 20mi (30km); elevation gain 1,300’ (430m) or 30mi (50km); gain 2,350’ (780m).


Day 2

Ulster County & New Paltz

Ride west into Ulster County to the historic town of New Paltz, surrounded by nature preserves and anchored by a state university. NY Times describes New Paltz as: “sporty, brainy, cultured, and beautiful. Cradled by a mountain range, surrounded by meadows and forested preserves cut through by a river, and specked with historic houses, shops and galleries.” On Huguenot Street, seven original stone houses are part of a 10-acre historic district and museum. It’s also a great spot for lunch – a new bakery recently opened that specializes in cheesecake that we can heartily recommend. If you are a craft beer enthusiast, visit the New Paltz Brewing Company. For dinner, venture out to the Falcon in nearby Marlboro for dinner and world-class live music.

Ride distance: 31mi (50km); elevation gain 1,770’ (590m) or 51mi (83km); gain 3,300’ (1,100m).


Day 3


Ride north and cross the Hudson on the remarkable walkway/bikeway over the Hudson; enjoy the view as you cycle across the longest elevated pedestrian bridge in North America. Cycle past the Culinary Institute of America which takes advantage of its location with the abundance of nearby farms and vineyards. Restaurant options at the Institute grounds including the Bocuse Restaurant, named after the Lyonnaise chef Paul Bocuse and which boasts an airy, bistro-style interior with a French menu that includes menu items from Paul’s first restaurant. Further north, visit the Franklin Roosevelt Museum and the Vanderbilt Mansion, a National Historic Site (there are 263 properties and districts listed in Dutchess County alone). Arrive to 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 and visit the eclectic shops that make up Montgomery Row. Stay at the Mirbeau Inn & Spa, which opened in 2019, and is reminiscent of a French chateau.

Ride distance: 31mi (50km); elevation gain 1,335’ (445m).


Day 4


Ride from Rhinebeck east through more of Dutchess County. Stop at a cool café/grocer for a mid-morning coffee and then continue through horse farm country to the village of Stanford, which has good lunch options. Visit Millbrook Vineyards on the Dutchess Wine Trail where you can taste Cabernet Franc, Chardonnay, Pinot Noir or Tocai Friulano. Or, if a late afternoon ice-cream is more tempting, you’ll pass by an option in Amenia, the nearest village to the Troutbeck Inn. This idyllic property sits on 250 acres so you’ll have a peaceful retreat. Play tennis, go for a swim or tuck into a book in the comfortable library reading room before dinner in the acclaimed restaurant.

Ride distance: 20 mi (33km); elevation gain 1,020’ (340m) or 31 mi (50km); gain 1,950’ (650m) or 38 mi (61km); gain 2,100’ (700m).


Day 5

Millerton & / or the Housatonic River Valley in CT

We have several options for you to consider on this day. Ride the Harlem Valley Trail to Millerton, voted one of America’s Favourite 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 some of the owners pickled, baked, jammed, stewed and simmered bounty. Or consider a loop 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. Arriving back to the hotel, relax and enjoy another dinner in the delightful dining room.

Ride distance: 20mi (32km); elevation gain 1,000’ (340m) or 36mi (60km); gain 2,700’ (900m).


Day 6

Departure Day

Depart at your leisure. The station at Wassaic is easily reached by taxi.


Buttermilk Falls Inn & Spa, Milton

Set on a 75-acre estate, this lovely 4-star inn on a working farm boasts 10 polished, individually decorated rooms in the main house. There’s an upscale farm-to-table restaurant and bar. Other amenities include a spa, a solar-heated sauna and an indoor pool, as well as a tennis court and a gym.

Mirbeau Inn & Spa, Rhinebeck

This chateau-style hotel has been described as something out of a fairy tale. Guest rooms have fireplaces and French-style soaking tubs. There is a massive spa, featuring treatment rooms with fireplaces, eucalyptus-infused steam rooms, Himalayan salt saunas, and an outdoor terrace with a heated pool. There’s even a fitness center and daily schedule of yoga classes. The restaurant Willow by Charlie Palmer is on site.

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 $2,850