hudson valley biking

Hudson Valley Biking Adventure

The massive Hudson Valley region, stretching from northern Westchester County and spanning both sides of the majestic Hudson River, is a wonderful, complex destination for outdoor enthusiasts and lovers of art, Americana, history and food, as well as spiritualists and wellness seekers. It’s the ideal spot for a cycling adventure that offers more than just physical activity—and with this curated itinerary, crafted in partnership with DuVine Cycling + Adventure Co., you can discover hidden trails suited for scenic rides, reflection in nature and athletic challenge, while enjoying the culture that this area has to offer. In the evenings, return to the Indagare-adored property Troutbeck for relaxation and a taste of upstate New York’s acclaimed food scene.

Plus—check out our new cycling itinerary with DuVine in Aspen!

What to Expect

On this special cycling journey, travelers will be able to go off the beaten track to explore the Hudson Valley’s verdant terrain and pastoral towns, just as the season changes from summer to autumn. In the evenings, return to the Troutbeck estate and have the option to enjoy spa treatments, farm-to-table meals and even whiskey tastings, as well as exploration in town and beyond to such sites of interest as the Storm King Art Center and Stone Barns, home to Dan Barber’s award-winning Blue Hill restaurant and Stone Barns Center for food and agriculture. Highlights of this itinerary include the opportunity to:

  • Join expert DuVine guides for daily, intermediate-level bike rides through the landscapes of the serene Hudson Valley, where the terrain shifts from wild forests and rolling hills to the vast banks of the Hudson River. Thanks to your guides and 24/7 van support, you will be able to make your cycling adventure as challenging or relaxed as you’d like it to be, while you make use of top-of-the-line cycling equipment, with daily bike maintenance servicing (e-bikes are also available).
  • Sample the best of upstate New York’s food scene with immersive dining and tasting experiences at local favorite restaurants, including Arethusa al Tavolo, and farm-to-table establishments led by top chefs—all accompanied by beverages sourced from nearby microbreweries and vineyards, as well as a growing network of local distilleries making hand-crafted whiskey, bourbon, and gin.
  • Supplement your cross-country biking activities with mountain biking or hiking.
  • Relax at one of Hudson Valley’s finest luxury estate hotels, Troutbeck.
  • Spend time enjoying Hudson Valley’s robust dining and art scenes on your own.
  • Add on a post-trip extension planned by the travel experts at Indagare to other areas of upstate New York, Maine, Vermont or beyond.

Level of Difficulty: This trip is classified at a Level Two (out of four) riding level, which is the ideal level for intermediate riders who enjoy a moderate exertion level, with the option to incorporate additional rides for a greater challenge.

Pricing: From $3,195, per person, based on double occupancy, with a minimum party size of six people. Final pricing will be determined by the final party size, room category and travel dates. Contact our team for custom party sizes and rates.

Cancellation Policy: We are happy to offer free cancellation up to 37 days prior to departure. Our team also strongly recommends that you consider purchasing travel insurance (our team can provide a quote).


Indagare can also arrange this trip for custom dates, with pre- or post-trip extensions if desired, that accommodate your schedule. We can also curate private biking trips to points east (such as Vermont and Maine) or further west to Zion National Park, Sonoma, Santa Barbara and beyond. Contact our team at to inquire.


The health and safety of our guests is our number-one priority. We are committed to upholding the highest safety standards, while providing world-class hospitality and a seamless travel experience. We are in close contact with all of our partners to ensure that they are committed to the health and comfort of our travelers by practicing enhanced sanitization and disinfecting procedures, respecting social distancing guidelines, and remaining as contactless as possible. For more information and questions about specific protocols that have been put into place to make your trip as safe as possible, please reach out to our team at

  • When
    Custom dates available upon request
  • Length
    4 days / 3 nights
  • Type of Traveler
    Adventurers , Foodies , Trailblazers

This Journey's Host

We are thrilled to partner with DuVine Cycling + Adventure Co.—a 2018 and 2017 Travel + Leisure World’s Best Tour Operator that designs and leads luxury bike tours in the world’s most amazing destinations—to bring you this biking adventure, complete with the best local guides and cycling experts who will help you test your physical limits while paving the road to unforgettable experiences. Click here to learn more about DuVine.

Curious to receive the full itinerary and join the trip? Contact us and find out more.

Trip Details

In preparation for the journey, members will also receive a comprehensive departure package that includes an itinerary, packing list, accommodations overview and other important information.

  • When
    Custom dates available upon request
  • Length
    4 days / 3 nights
  • Group Size
    Up to 8 travelers
  • Host
    DuVine Cycling + Adventure Co.
  • From


  • Accommodations at Troutbeck Hotel (3 nights)
  • Daily breakfast, lunch, nutritional snacks, après-velo cocktails and three (3) gourmet dinners at the local restaurant including local wine, beer or spirits with every meal
  • All guided biking, transfers and activities, as indicated in the itinerary
  • The use of top-of-the-line biking equipment for the duration of the trip. E-bikes are also available to rent for an additional supplement
  • The services of our Hudson Valley and DuVine partners, including expert local guides and dedicated van support so that you can cycle at your own pace
  • Daily bike maintenance and support, as well as luggage transfers as needed
  • Transfer between the Wassaic Train Station and Troutbeck upon arrival and departure
  • Gratuities for hotel service and baggage porters


  • Air transportation to and from New York, as well as travel insurance (strongly recommended)
  • Meals not specified and premium alcoholic beverages other than those included in meals
  • Personal items and expenses, including additional activities
  • Liability for change in itinerary due to reasons beyond our control (change in flights, cancellations, political disturbances, natural phenomena)
  • Gratuities for guides
Curious to receive the full itinerary and join the trip? Contact us and find out more.

What To Read

Indagare has selected articles from our website and magazine to prepare you for your journey. Peruse inspiring slideshows, insider tips, reading lists and more.

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