NY Empire State Trail: Hudson Valley Greenway

Hudson Valley Bike Tour Itinerary

DAY 1: We start our tour with a rental bike fitting at 2:00pm, orientation at 5:00pm and then dinner together. Our hotel is in downtown Troy, which The New York Times praised as having “one of the most perfectly preserved 19^th century downtowns” in the country, so if you arrive early, be sure to explore the historic district’s boutiques, art galleries, antique dealers and bookstores. The hotel is across the street from the Hudson River, our touchstone for the entire tour. 0 miles.

DAY 2: After a hearty breakfast at our hotel, we immediately meet up with the Hudson and cross it on the Green Island Bridge. Heading south on the Empire State Trail (EST), you’ll see the Albany skyline and the New York State Capital, a breathtaking example of Renaissance Revival architecture. 

After crossing the Hudson a second time, we ride along a former trolley line where cars traveled up to 60 mph until 1929. The Albany-Hudson Electric Trail, as this stretch of the EST is called, leads to horse farms and small lakes, then old mills and the scenic Stuyvesant Falls.

The small city of Hudson, once a hub for the whaling industry, welcomes us with a stunning outline of the Catskill Mountains. Take time to stroll the city’s downtown, full of galleries, antique shops, and boutiques. Our hotel is right in the middle of it all. 48 miles, elevation +2022’/-2113’.

DAY 3: It’s a day with a little bit of trail and a lot of country roads, with apple orchards, miles of stone walls, handsome barns and charming small towns.

We cross the Hudson once again via the Kingston-Rhinecliff Bridge, offering dizzying views of the Hudson and surrounding hills. Kingston, our home for the night, played an important role in the abolitionist movement. It is where the once enslaved Sojourner Truth fought to rescue her son, who was illegally sold out of state. Fearless in a courthouse, Truth won this case, as well as two more in her lifetime. We ride through a new state park named in her honor as we enter the historic city of Kingston. Dinner is on your own—Kingston has a plethora of options. 35 miles,elevation +1079’/-1258’. 

DAY 4: Be camera-ready when you ride, as today’s route has some killer views. The bike trails today are fantastic, taking you first past caves and kilns where natural cement was mined and cured. Rosendale cement was recognized as the best natural cement in North America and was used to build famous structures such as the Statue of Liberty, the Brooklyn Bridge and the U.S. Capitol Building.

Before we reach the outdoor adventure mecca of New Paltz, we come upon a beautifully preserved French Huguenot settlement dating back to 1678. Huguenot Street, lined with handsome stone houses, is the longest continuously inhabited street in the country. It’s worth time off the bike to explore. 

Finally, for a more leisurely view of the Hudson, take time to ride (slowly) across the famous Walkway over the Hudson, a 212-foot-tall steel cantilever railroad bridge that has been converted to a pedestrian/bicycle park. The Walkway takes us to our overnight destination of Poughkeepsie. 31 miles, elevation +1229’/-974’.

DAY 5: Wetlands and tiny lakes dot the landscape of today’s ride, giving it a pleasant wilderness vibe. Take some time to visit the Hopewell Depot Museum and learn about the region’s railroad history. Along the way we’ll also pass the Green Haven Correctional Facility, a maximum security prison where infamous inmates such as Mark David Chapman (John Lennon’s assassin) reside. We will spend the night in Brewster. 45 miles, elevation +1587’/-1309’.

DAY 6: As you start the day riding on woodsy trails, you will find it hard to believe that you are less than 75 miles from the Big Apple. Crossing over the New Croton Reservoir, one of New York City’s water sources, you enter the Kitchawan Preserve, which served as a research station for the Brooklyn Botanic Gardens until the late 1980s. In late spring the area is a magnet for migrating birds and butterflies. Our last overnight before New York City is Yonkers, the state’s fourth largest city by population. 45 miles, elevation +1282’/-1728’.

DAY 7: Big Apple, here we come! From here on out, it’s a bustling and vibrant urban biking experience, and while you’re on trails the entire way, the bicyling traffic is brisk and there are many intersections with vehicular and pedestrian crossings, so bring your best defensive cycling skills along.

After a short jaunt through the Bronx, we enter Manhattan, with stunning overlooks of the George Washington Bridge and the New Jersey Palisades.

Just a few blocks from the trail is the 9/11 Memorial and Freedom Tower, a worthy detour before you reach the grand finale, Battery Park, where you’ll have a wonderful view of the Statue of Liberty.

Because no trip to the Big Apple would be complete without it, we will take a subway ride back to Yonkers and celebrate our monumental journey at a final farewell dinner. 25 miles, elevation +928’/-1076’.

As e-bikes are not allowed on the trails in Manhattan, we will offer a sightseeing option on this day for e-bike riders and anyone else who is not comfortable with urban cycling.

DAY 8: You are free to leave at your leisure or take the WomanTours shuttle back to our starting hotel or the Albany Airport, arriving by 1:00pm. We hope you had a fabulous time! 0 miles.