‘Tis the season for bike rides, NYC!
Spring has surely sprung, and while we love a good citibike ride, sometimes it doesn’t quite cut it.
If the first warm days of the season have you itching to get outside—to feel the breeze pick up as you ride and watch the landscape slowly shift from city streets to rolling countryside—you’re not alone. There’s something about this time of year that calls for a full day (or weekend) adventure.
And for those who crave both the rhythm of a long-distance bike ride and the richness of stepping into the past, there’s a route that delivers on all fronts.
Stretching roughly 100 miles north from New York City, the Empire State Trail offers one of the region’s most rewarding cycling experiences, guiding riders through riverfront paths, quiet towns, and lush stretches of the Hudson Valley before arriving in Kingston—New York’s first capital.
Kingston is a living snapshot of early America. With deep roots in Revolutionary War history and a strong imprint of Dutch heritage, the city offers cobblestone streets, centuries-old architecture, and stories that linger long after you’ve dismounted your bike.
Though tackling all 100 miles is a bit daunting, the beauty of this adventure is choosing your own path along a much longer one.
Where to Start: Choosing Your Own Adventure
While the route technically starts at the Battery in Lower Manhattan, you don’t have to do all 100 miles in one go if you aren’t feeling like a pro cyclist today.
- The Full Century: Start at the Hudson River Greenway in Manhattan and follow the trail north through the Bronx.
- The “Head Start”: Take the Metro-North (Hudson Line) to Tarrytown or Croton-Harmon to skip the city congestion and jump straight into the greenery.
- The Poughkeepsie Pivot: For a manageable 30-mile day trip, take the train to Poughkeepsie and ride the Empire State Trail across the Walkway and north into Kingston
The Route: From Skyline to Shoreline
The journey to Kingston follows the Hudson Valley Greenway section of the Empire State Trail. It is a masterclass in varied scenery. You’ll begin by hugging the Hudson River, eventually transitioning onto paved rail trails that feel worlds away from the city’s frantic energy.
- The Path: Much of the route is car-free, utilizing the North and South County Trailways and the Maybrook Trailway.
- The Vibe: Expect a steady, gentle incline as you head north, rewarded by breathtaking views of the Catskill Mountains as you approach Ulster County.
- The Highlight: Crossing the Walkway Over the Hudson in Poughkeepsie. At 212 feet above the water, it is the longest elevated pedestrian bridge in the world and provides a panoramic view that makes every mile pedaled worth it.
Key Route Details
- The Path: You start at the tip of Manhattan (Battery Park) and follow the Hudson River Greenway north. You’ll eventually connect to the North County Trailway and South County Trailway in Westchester, which are paved, car-free paths built on old railroad beds.
- Surface: Most of the trail is paved with asphalt or smooth crushed stone. However, the final approach into Kingston involves some on-road sections through city streets.
- The High Point: One of the most spectacular parts of the ride is crossing the Rosendale Trestle, a massive bridge that offers panoramic views of the Rondout Creek and the surrounding mountains just before you reach Kingston.
- Logistics: Many cyclists do this as a multi-day trip, staying overnight in towns like Yorktown Heights or New Paltz. If you don’t want to bike back, you can take the Amtrak from Rhinecliff (just across the river from Kingston) or the Metro-North from Poughkeepsie back to Grand Central.
The Destination: A Tale of Two Tides
Arriving in Kingston feels like finishing a race in a different century. As New York’s first capital (established in 1777), the city is uniquely split into two distinct, historic hubs:
- The Stockade District (Uptown): This is the city’s historic heart. Here, you’ll find the Senate House, where the first New York State Senate met before the British burned the city. The architecture is a stunning blend of 17th-century Dutch limestone houses and pre-Revolutionary charm.
- The Rondout (Downtown): Located along the creek, this waterfront district was a bustling 19th-century maritime port. Today, it’s home to the Hudson River Maritime Museum and a vibrant strip of galleries and eateries.
What to Expect: Gear, Grades, and Grains
Before you clip in, here is the lowdown on the logistics:
- The Return: If your legs have turned to jelly by the time you reach Kingston’s cobblestones, don’t panic. You can catch the Amtrak from nearby Rhinecliff (just across the river) or take a bus back to Port Authority.
- The Terrain: The trail is largely paved and exceptionally well-maintained, making it suitable for road bikes, hybrids, and gravel bikes alike. While there are some rolling hills in Westchester and Putnam counties, the rail-trail sections are famously flat.
- Fueling Up: The trail passes through “trail towns” like Brewster, New Paltz, and Rosendale. You’re never too far from a craft brewery, a local bakery, or a bike-friendly cafe.
To learn more, visit the Empire State Trail’s official website.
