Pedal Through the Peaks of the Hudson Valley on These Overnight Bike Tours | Outdoors | Hudson Valley | Chronogram Magazine
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Pedal Through the Peaks of the Hudson Valley on These Overnight Bike Tours 

These 4 guided trips showcase the best of the area’s amenities while traversing local terrain

click to enlarge GOTHAM BICYCLE TOURS
  • Gotham Bicycle Tours

For lovers of the outdoors, overnight bike tours are a great alternative to the classic weekend getaway, showing you a region in a new light. Upstate New York, with its hills and valleys, winding waterways, and sprawling vistas, offers a dynamic landscape perhaps best viewed from atop a bike. The guided bicycle trips below range from one to five nights, and all of them have route variations throughout, so both novice and experienced bikers can enjoy the landscapes and activities. Wine tastings, national historic site tours, visits to top-rated restaurants, and other activities break up the cycling, while luxury hotel accommodations let you rest and relax after a day in the saddle. Many of these guide companies have options for private group tours as well as corporate getaways, so there’s plenty of ways to have the best trip possible. Learn about what each of these upcoming tours offers, and maybe even start planning your next vacation.

Gotham Bicycle Tours

click to enlarge GOTHAM BICYCLE TOURS
  • Gotham Bicycle Tours

Geared towards city dwellers looking to immerse themselves in the Hudson Valley, Gotham Bicycle Tours offers custom guided overnight experiences for groups of up to 10 people. For $500-$800, company founder and experienced biker Lukas Herbert will create a custom GPS-mapped route and itinerary based on a group’s physical ability and desired stop points that is theirs to keep regardless of whether or not they book a tour. A sample three-day itinerary for a Hudson Valley tour includes stops in Wassaic, Harlem Valley, and Wallkill Valley. Visit a winery, tour some farmland, and even ride across the scenic Walkway Over The Hudson. At night, sleep under the stars at a campground equipped with bathrooms and showers, where meals are provided. Or if you’d rather, groups also have the option to stay at a hotel. A minivan driven by an experienced biker follows the group to hold their equipment and provide basic bike repairs and maintenance. For groups of six and under, tours cost about $900 per day and include the leader and minivan, insurance, some meals, and rest stop snacks and beverages. Camping gear, bikes, and accommodations are not included. The routes are designed to be near train stations and bus stops for easy transportation. For more information or to schedule a consultation, call (917) 748-1119 or email

Backroads Hudson Valley Bike Tour

If exploring some of the Hudson Valley’s quaint towns and staying in hotels with stunning nature views sounds like the perfect vacation, consider booking a weeklong tour with Backroads, which offers adventure tours in 64 countries. For five days and four nights, bike at the base of the Shawangunk Mountains, trek along the Dutchess Rail Trail, eat at the Culinary Institute of America in Hyde Park, and more on a loop that stretches from Beacon to Saugerties. Rest for the first two evenings at Buttermilk Falls Inn & Spa, where travellers can refuel at the Inn’s farm-to-table restaurant. Then take in views of the Esopus Creek falls from a room at the Diamond Mills Hotel & Tavern, where bikers stay for the second half of the trip. The trip begins at $3,399 per person for double occupancy rooms, and an extra $600 for single-occupancy ones. It includes the rider’s choice of one of Backroads’ custom fleet of titanium bikes (the Carbon Bike costs an extra $400), all breakfasts, four lunches and dinners, snacks and beverages, and fees for any planned activities. There’s also a van that bikers can ride in at any time. Reservations for September and October 2022 tours are being accepted. They can be made online, and the company can be contacted at (800) 462-2848 or via email.

DuVine Cycling + Adventure Co.

click to enlarge Troutbeck - DUVINE CYCLING + ADVENTURE CO.
  • DuVine Cycling + Adventure Co.
  • Troutbeck

Are green pastures and farm fresh eateries calling your name? Reserve a spot on DuVine Cycling + Adventure Co.’s weekend-long Hudson Valley Bike Tour. This four-day, three-night trip through some of the area’s most charming farmlands uses Troutbeck, a historic hotel and retreat in Amenia, as its home base. Each day brings a new destination: bike to the Housatonic River Valley in Connecticut and see some 1800s-era covered bridges, head north to Ancramdale and taste locally made whiskey, and travel to historic Rhinebeck for one last lunch. Each day includes farm-to-table eats at the various destinations, as well as meals at Troutbeck hosted by executive chef Gabe McMackin, who sources local ingredients for his culinary creations. Bookings are available for the October 18-21 trip, and cost $3,695 per person. Accommodations, bikes, all meals (at the hotel and elsewhere), DuVine gear and clothing, DuVine’s guides and support vehicles, transportation to and from the tour, and fees for all activities outlined in the tour itinerary are included. There is an extra charge of $675 for travellers who want a single-occupancy room. Tips for DuVine guides, airfare, and travel protection are not included. Book by calling (888) 396-5383, or contact DuVine via email for more information.

Great Freedom Adventures

  • Great Freedom Aventures

Perfect for architecture lovers, Great Freedom Adventures’ six-day, five-night bike tour gives cyclists the chance to immerse themselves in the Hudson Valley’s history. Take in the fall foliage and landscapes that inspired the Hudson River School of painters before viewing the artwork at Frederic Church’s architectural masterpiece, Olana, in Hudson. See where Washington Irving got his inspiration for “Rip Van Winkle” at Poets’ Walk Park, and tour the Vanderbilt Mansion and the Livingston family’s Clermont Estate and Montgomery Place. For two nights, bikers choose between staying at the Inn at 34 or Hudson B&B, both of which include breakfast. Then spend three nights at Beekman Arms & Delamater Inn in Rhinebeck, the oldest continually operating inn in the country, which has been hosting travellers for more than 240 years. The tour costs $3,295 per person for double-occupancy facilities, and an extra $895 for single-occupancy ones. Bicycle and helmet rental, hotel accommodations, various meals, two guides and van support, museum and historical site admissions fees, vineyard tours and wine tastings, and gratuities for meals and excursions are all included. Guests are responsible for some meals and can bring their own bike if they desire. Book online, or for more information, contact Great Freedom Adventures at (508) 545-1864 or

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