Winding road lined with fall trees in upstate New York.
Cyclist biking down wooded path in Hudson, NY.
Two Backroads guests photographing a goat in a barn.
A grove of orange trees in fall lining a river.
Cyclist picking apples in an orchard.
Two cyclists riding on a coastal road in Hudson, NY.
Two cyclists posing under a sign that reads "Catskill Park, Woodstock".
Autumn leaves in Hudson, NY.
Cheese, fruit and nut plate.
Backroads leader holding snack plate in front of van.
Trees and plants along the Harlem Valley Rail Trail.
Hyde Park, NY, USA: A male red-winged blackbird (Agelaius phoeniceus) perched on stalk near a pond.
Spring colors begin to show along a country road in the Catskill Mountains of southeastern New York.
Hudson River in upstate New York with Catskill Mountains in the background.
Street signs in town of Woodstock, NY, Ulster County, Catskill Region
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Hudson Valley & Catskills Bike Tour

New York's Mountain Playground & Farm-to-Table Charm

Couples, Friends & Solos

5 days 4 nights

Activity Level: 2-4

Premiere Hotels

From: $3,899 - $3,949 pp dbl occ

($1,600 for sgl occ) plus 8.125% tax

Between the Big Apple and Albany lies a landscape of red, white and blue. The lush red apples of countless orchards. The white limestone mansions along the Catskills. The Hudson River, blue in the warm sunlight. Embark on a vibrantly colored journey into the heart of the Empire State, one of the country's most historic and captivating regions.

New York Hudson Valley & Catskills Bike Tour
New York Hudson Valley & Catskills Bike Tour

New York

Start/End Rhinebeck

Start/End locations may vary. Do not book flights until your trip details are confirmed.


  • Bike the peaceful rolling hills, woodlands, picturesque towns, quaint historic homes and meandering valleys of upstate New York
  • Explore a region rich in history and culture, known for Woodstock, the legends of Rip Van Winkle and the Hudson River Art movement
  • Marvel at superb vistas of the Catskills and postcard-perfect countryside, just a short trip from New York City
  • Taste the local bounty—delicious fresh fruit, vegetables, cheeses, wine, beer and cider


Accommodations may vary based on departure date.
5 Days Premiere Hotels
Accommodations may vary based on departure.
Days 1-2

Begin your journey in the Hudson Valley with a ride along the lovely Catskill Mountains and see for yourself why it’s drawn artists and writers for centuries | Take in breathtaking views of the mountains as you ride around Ashokan Reservoir, which serves as a fresh source of drinking water for New York City | Lunch in the village of Hunter, a destination loved for its excellent skiing, climbing and hiking | Bike past acres of farmland, orchards, green pastures and white church steeples | Explore the unique galleries, shops and cafés of legendary Woodstock, where "peace, love and happiness" still reign | Ride along the scenic Esopus Creek to the village of Phoenicia, a haven which many musicians and artists call home | Relax to the sounds of a babbling brook at our valley retreat.

Exterior view of Woodstock Way hotel
Woodstock Way
| Premiere Hotel

With peaceful surroundings and a conscious, modern design, this contemporary boutique hotel sits tucked behind a waterfall beside a babbling brook and has attracted musicians, artists and even bootleggers in its time.

Days 3-5

Bike rolling hills sprinkled with apple trees, vineyards, flower gardens and impressive homes | Follow a section of the spectacular Harlem Valley Rail Trail, passing beautiful farms, woods and rolling pastures | Sip and swirl local varietals at a vineyard | Savor fresh farm-to-table cuisine at Troutbeck, our stylish boutique hotel | Explore the peaceful woodsy trails of Taconic State Park on foot | Cross the Kingston-Rhinecliff Bridge, an impressive architectural achievement that stretches across the Hudson River | Ride through lush meadows and pastureland sprinkled with gorgeous horse farms | Rejuvenate with a visit to The Barns, our hotel’s tranquil, newly built complex featuring saunas, treatment rooms, studio classes and more.

Exterior view of Troutbeck Manor House and grounds
| Premiere Hotel

Rest in this idyllic estate hotel on the eastern edge of the Hudson Valley, surrounded by 250 lush acres and sycamores planted in 1835. (pool, spa)

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Activity Level: 2-4

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Daily Route Options

* Includes shuttle.
Day 1
Level 1 | 16 miles* | 500 ft. gain
Level 2 | 25 miles | 2400
Day 2
Level 2 | 26 miles* | 1700 ft. gain
Level 3 | 35 miles | 2200 ft. gain
Level 4 | 47 miles | 2900 ft. gain
Day 3
Level 2 | 22 miles* | 2100 ft. gain
Level 3 | 36 miles* | 2700 ft. gain
Level 4 | 54 miles | 3200 ft. gain
Day 4
Level 2 | 21 miles* | 600 ft. gain
Level 3 | 42 miles | 1100 ft. gain
Level 4 | 51 miles | 2600 ft. gain
Day 5
Level 2 | 27 miles | 1900 ft. gain

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Click the arrow to see all bike options.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Canyon Endurace SLX 9 Di2
Canyon Endurace SLX 9 Di2
Canyon Endurace SLX 9 Di2

Ride like a pro with the top-of-the-line carbon Canyon Endurace CF SLX 9 Di2. A performance-first flagship endurance bike engineered for comfort and race-level riding.

$650 rental fee; subject to availability

Co-Motion Torpedo Tandem Bike
Co-Motion Torpedo Tandem Bike
Tandem Bike

This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee

Also Included

  • All breakfasts, 5 lunches, 3 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our Help Center.

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