Top Three Day Trips along the Hudson Valley Greenway Trail

Discover the best day trips to New York’s Empire State Trail. 

This post contains our Top Three Day trips along the Hudson Valley Greenway section of the Empire State Trail (between Albany and Manhattan) 

All of the trailheads for our Top Three Day Trips on the Hudson Valley Greenway can be easily accessed by car or train, making it a breeze to travel from Manhattan or Albany.  

Day Trip 1. Walkway Over the Hudson

Estimated Mileage – 18+ miles

Mostly off-road paved trail with a scenic bikeable walkway over the Hudson River

Start your day off in Downtown Poughkeepsie with a coffee at the Poughkeepsie Grind; just a short ride from the train station and with lots of public parking. The post-industrial city of Poughkeepsie has been revitalized by the addition of the Walkway Over The Hudson. Once a train bridge, the Walkway Over the Hudson will account for the first 1.5 miles of the start of your ride or walk. If you choose, you can instead start your day with a short venture off the trail to tour the beautiful grounds of Vassar College. Begin at The Walkway Over The Hudson State Park where you will travel through the center of downtown Poughkeepsie before stretching over the Hudson River on the Walkway. Once you cross the Hudson, the walkway turns into the Hudson Valley Rail Trail. The Rail Trail will lead you into the thriving village of New Paltz. Stop to enjoy a riverside lunch and drink at The Clemson Brothers Brewery. If you are a history buff, tour Historic Huguenot Street just off the trail. Made up of 7 historic stone house museums, a church, burial ground, and a replica wigwam. The historical street documents the history of early settlers in the region. Return across the Walkway over the Hudson and into Poughkeepsie to get back to your car or to hop on the train. 

Day Trip 2. Hudson

Estimated Mileage – 20+ miles

A mix of on-road and off-road paved trails.

Start your day with a waterfront photo-op in Hudson at the Henry Hudson Riverfront Park. Just Steps from the train station and with public parking, the river-side park intersects with the Hudson Valley Greenway Trail.  If you choose, travel off the trail into the Downtown area for coffee and breakfast at one of the local establishments like Wm. Farmer and Sons. Start on the trail and travel south on the on-road section for roughly 4.5 miles to the Olana State Historic Site to tour a one-of-a-kind home built in the late 1800s, and the 250 acres of natural landscape around it.  Upon returning to the United States after an 18 month-long trip to the Middle East, Hudson River School Painter and Landscape Designer, Frederic Church and his family settled south of the City of Hudson where they designed an impressive estate with Middle Eastern influences and eclectic furnishings. The one-of-a-kind home was saved from destruction in 1966 and has since been undergoing restoration and currently operates as a public park. After your visit to Olana, head back north on the trail to Hudson. Choose to explore the town or continue north on the Albany Hudson Electric Trail. It is recommended to turn around and head back to Hudson once your hit the Stuyvesant Falls area. 

Day Trip 3. Hudson River Greenway

Estimated Mileage – 12.5+ miles

Off-Road Paved Bike Trail 

For lifelong residents, upstate dwellers, or out-of-town tourists, bike touring the Hudson River Greenway is an affordable way to see some of the most famous landmarks in New York City.  Start on the trail at Fort Tryon Park, where you can stop for a photo-op at The Met Cloisters. Head south along the Hudson River Greenway through Fort Washington Park, Riverside Park, heading south along the edge of the Hudson River. For a unique tourist experience, stop at the Intrepid Sea, Air, and Space Museum. The real prize lies in the last tail of the tour. Ride around or go inside and tour the 9/11 memorial, museum, and One World Trade Center. For a picturesque end to your ride arrive at Battery Park where you can see The Statue of Liberty and Ellis Island across the Harbor

Now more than ever our locally owned and small businesses need our support. Traveling in your own backyard is the perfect way to support the local economy, see new things, and in the case of the Hudson Valley Greenway, get some exercise and fresh air while doing it. Bike touring day trips provide a way to see multiple points of interest in a single day. Be sure to check out our cycling gear to be properly prepared for your next day trip. Who knows you may even want to tour the entire trail.

We want to make sure your next experience on the trail is enjoyable and unforgettable. We offer outdoor equipment reviews and world-class advice on the Empire State Trail and how to travel it.