From top trails to the right bikes, our guide will help you get in gear to plan your next active getaway!
Backroads
Hudson Valley & Catskills Tour
Starts/ends in Rhinebeck
Cycle throughout the rolling hills of the Catskills in Ulster and Greene counties on days one and two. You’ll take in views of landmarks such as the Ashokan Reservoir, Hunter Mountain, downtown Woodstock and Phoenicia, and the Esopus Creek. Days three through five highlight the pastoral charm of Dutchess County along the Harlem Valley Rail Trail, with visits to the Kingston-Rhinecliff Bridge and Taconic State Park.
Accommodations: Woodstock Way (Woodstock) and Troutbeck (Amenia)
Best perk: A wine tasting at Millbrook Winery
Dates: June through October
Pricing: 5 days/4 nights from $3,949/person
Lunch and dinner included, van support, cultural visits, coach transfer
Ciclismo Classico
HV Cornucopia Tour
Starts/ends in Rhinebeck
Calling all history buffs! This 225-mile tour is focused on Hudson Valley: While peddling through Pine Plains, Staatsburg, Hyde Park, High Falls, and Stone Ridge, you’ll learn all about what makes the region rich with culture. Landmarks include the Old Rhinebeck Aerodrome, the former Prohibition hideout of bootlegger Dutch Schultz, various old-world mansions, and Bard’s Fisher Center. Note: bikes are not included; bring your own or contact Ciclismo for a rental.
Accommodations: Beekman Arms & Delamater Inn (Rhinebeck) and The 1850 House Inn (Rosendale)
Biggest perk: Lunch at the Culinary Institute of America before riding over the Walkway over the Hudson
Dates: Contact tour company
Pricing: 6 days/5 nights from $2,995/person
Lunch and dinner included, van support, cultural visits, museums
Discovery Bicycle Tours
Empire State Trail Tour
Starts in Battery Park and ends in Albany
If you want comprehensive highlights of the EST’s Hudson Valley Greenway Trail, this is it. Discovery offers six days of 30–47 miles each and stops by popular biking destinations such as: the 911 Memorial, Croton Reservoir, The Walkway, the Rosendale Trestle, and Kinderhook Lake in Niverville.
Accommodations: Multiple hotels including Beekman Arms (Rhinebeck) and The Wick (Hudson)
Best perk: The water features—throughout the trip, you’ll ride along (and across) the Hudson River, Putnam County’s famous lakes, and even get lunch next to the pretty Nassau Lake in Rensselaer on your last day
Dates: June through October
Pricing: 6 days/5 nights from $2,895/person
Lunch and dinner included, bikes included, van support
Duvine Cycling + Adventure Co.
Hudson Valley Tour
Starts/ends in Wassaic
DuVine has been named one of the world’s best tour operators by Travel + Leisure four years in a row and it’s no wonder: This excursion is equal parts country charm and stylish retreat and great for bikers of all levels. You’ll experience local fare at farm-to-table dinners, cider and spirits tastings, and learn the history of Dutchess County horse farms.
Accommodations: Troutbeck (Amenia)
Best perk: On day two, bike along the Appalachian Trail to Connecticut’s Housatonic River Valley. Here, you’ll cycle across photogenic covered bridges (all built in 1842) and have a hyperlocal lunch at a farm in Millbrook or Millerton
Dates: June through October
Pricing: 4 days/3 nights from $4,195/person
Lunch and dinner included, bikes included, van support, cultural visits, coach transfer
“The Hudson Valley is a fantastic place to ride a bicycle. It has everything from Big City hustle-and-bustle to quiet rural areas through farms and orchards. There are many trails that wind through valleys and over hills and across the Hudson River. And of course, it’s packed with history and art. Great food options, too.” —Paul Kingsbury, Wilderness Voyageurs
Great Freedom Adventures
Hudson Valley Tour
Starts/ends in Hudson
We think this tour is the best bang for your buck: the itinerary includes top landmarks and sites on the east side of the Hudson, including Olana, the Clermont Estate, Poet’s Walk in Red Hook, many luxurious mansions (from Wilderstein to Springwood to Val-Kil), and award-winning wineries. Your homebases will be Hudson and Rhinebeck—so expect some of the best cuisine the region has to offer.
Accommodations: Inns—such as the Hudson Whaler (Hudson)—vary per tour
Best perk: In the evening of day two, you’ll head to Hudson’s waterfront and hop aboard a narrative cruise. Take in the Catskills, the charming Hudson-Athens Lighthouse, and quaint HV river towns while sipping on local wine and beer
Dates: July through September
Pricing: 6 days/5 nights from $3,595/person
Lunch and dinner included, bikes included, e-bikes, van support, cultural visits, museums, coach transfer
Pocono Biking
Hudson Valley Inn to Inn Tour
Starts in Kingston and ends in Valhalla
The Empire State Trail is 750 miles long—and this tour allows guests to hit as many trailways as possible. (Seven to be exact.) Day one starts at the Wallkill Valley Rail Trail (with gorg views of the Rosendale Trestle and backdrop of the ‘Gunks); day two includes the Walkway and Maybrook section, which traverses through dense, whimsical woods and wetlands; day three is the peaceful Putnam Trailway; and day four finishes off along the Westchester North County Trail and pretty Kensico Dam.
Accommodations: The Roundhouse (Beacon), and the Castle Hotel & Spa (Tarrytown)
Best perk: After over 100 miles of riding, gather with the group for a farewell dinner in downtown Tarrytown then spend the night in luxury at the Castle, a converted inn that dates back to the early 1900s
Dates: July through October
Pricing: 4 days/3 nights from $1,119/person
Lunch and dinner included, e-bikes, van support, coach transfer
Wilderness Voyageurs
NY Empire State Trail Tour
Starts in Manhattan and ends in Schenectady
Clocking in at 45 miles a day and incorporating six HV counties, this EST tour offers just about everything: iconic NYC tourist destinations (hello Lady Liberty); picturesque rail trails from Westchester to Dutchess counties; artsy stops along the trail connecting Kingston to Hudson; and AHET—the Albany-Hudson Electric Trail. Some bikers say it’s one of the best EST sections due to its variety of pretty views, from woods and streams to wetlands and rolling hills.
Accommodations: Curry Estate (Hopewell Junction), Hotel Kinsley (Kingston), and The Wick (Hudson)
Best perk: Your hard work pays off on day six: after cycling the Erie Canalway Trail, you’ll stop at Cohoes Falls—the second largest waterfall in the state
Dates: June through October
Pricing: 6 days/5 nights from $2,470/person
Lunch and dinner included, bikes included, van support, cultural visits, coach transfer
Chain Reaction
The team behind Diamond Mills Hotel and racing company Alpha Win recently launched Hudson Valley Detours—a six-day biking tour (which debuted in May) that explores top landmarks and towns, including Saugerties, Kingston, New Paltz, Woodstock, Catskill, and Hudson. Guests will have access to R&R treatments at Diamond Mill’s on-site Waterside Spa and farm-to-table dinners at BLACKBARN. Other excursions include kayaking in the Esopus Creek and picnics along the Ashokan Reservoir. For more info and fall bookings, visit alpha.win or diamondmillshotel.com.
Trail Tips
Electric Avenue
“E-bikes are such a great addition to the world of cycling. They can enhance range, comfort, stamina, and overall experience for several styles of riding—whether that’s removing the worry about keeping up, shifting the focus away from the effort of cycling (so greater emphasis can be given to enjoying your surroundings), going longer distances on flats, or enjoying the climbs. E-bikes are game changers especially if traveling with a companion whose experience level is different from your own.” —Mia Liefeld, DuVine Cycling
“An e-bike is a great option for those who want a little assistance. The ones we generally use are called Class 1, which means there is no throttle and the battery power provides an assist up to 20 mph. Our e-bikes usually have four levels of assistance, and you can even turn off the battery. You still need to pedal the bike even with the assist turned on. It basically multiplies the effort you put in by pedaling.” —Thistle Cone, Discovery Bicycle Tours
Do Your Homework
“If I’m going on a tour, I always like to go through the itinerary and do some reading about where I’m going, looking up towns and attractions so I know a bit more about what to expect. Plus, there are always some fascinating facts online about the places we’re visiting. It helps me enjoy the trip more and be a better guide.” —Dave Kraus, Ciclismo Classico
“I think it’s fun to read the history of a new region you visit. Or even read a historical novel set in the area. The beauty of our tours is that you can just show up, and we provide bikes, leaders, lodging, van support, and background on the areas you visit.” —Thistle Cone
You can only bike one HV trail. Which is it?
“It’s got to be the Wallkill Valley Rail Trail. In 16 miles, it offers so much easy riding, and shows off the Huguenot neighborhood in New Paltz, a craft brewery, a forest café along the trestle, and historic cement mines and lime ovens in Rosendale. Plus, it’s just been renovated as part of the Empire State Trail, and I’ve included it on our Ciclismo Classico Hudson Valley Tour.” —Dave Kraus, Ciclismo Classico
“Our Hudson Valley trip designer, Edd Naud, has an immense love of the Harlem Valley Rail Trail and considers it a highlight of DuVine’s trip. It moves you through a lovely and diverse landscape, and he loves stopping in Millerton for a mid-ride coffee.” —Mia Liefeld, DuVine Cycling
“The new Empire State Trail—running from Battery Park in Manhattan all the way up to and beyond Albany—is a favorite. It has lovely fresh pavement with a few sections of smooth, natural rail trail surface. The EST connects quaint Hudson Valley towns making it easy to find lodging and meals along the route. Each day is a little different from the last, so it stays interesting and new the entire way.” —Paul Kingsbury, Wilderness Voyageurs
Wheels up
Not all bikes are created equal. Here are the most common types and what they’re suited for.
Cyclocross
Terrain: mixed-surface
Best for: off-road
City
Terrain: streets, parks
Best for: commuting
Mountain/ Trail
Terrain: streets, parks, forests, races, mountains
Best for: off-road or rugged trails
E-bike
Terrain: all types
Best for: long-haul trips, hills and inclines
Road
Terrain: streets, races, highways
Best for: smooth pavement
