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The city may be blanketed in snow right now, but it's not too early to start thinking about hitting the trails and getting back to nature. Cycling season is almost here, and if you’re plotting your first big ride of spring, you'll want to make it a scenic one. Bike rental company Holland Bikes analyzed more than 5,000 cycling trails across New York State to compile the 2026 Trail Index identifying the most picturesque bike trails in New York.
The company looked at ratings, popularity and, crucially, how many photos each trail inspires. The top ten list is comprised of spots that earned a "picture perfect score" of 90 or higher.
Leading the pack is the Blackhead Range Traverse via Kaaterskill Falls in Haines Falls, with a near-perfect 94.14 score. The two-tiered waterfall, tucked into the eastern Catskill Mountains, has long been a favorite for painters and hikers. Now cyclists are getting in on the action. In fact, Kaaterskill routes appear four times in the top ten, as the dramatic cascade regularly stops riders in their tracks.
Close behind is Bull Hill, South Beacon Mountain and North Beacon Mountain in Cold Spring, where sweeping Hudson Highlands views and rocky ascents earn a 92.42 score. Not far off, the Lake Minnewaska–Millbrook Mountain–Gertrude’s Nose–Lake Awosting route in Kerhonkson pairs cliff-edge vistas with serene water crossings, clocking in at 92.12.
One clear trend stands out. Trails with the highest “photos per kilometer” scores, such as Inspiration Point and Kaaterskill Falls via the Kaaterskill Rail Trail, are outperforming longer endurance routes. Riders are planning loops around lookout points, waterfalls and ridgelines rather than chasing distance. The Inspiration Point and Kaaterskill Falls Loop, for example, racks up an impressive 3.25 photos per kilometer.
And while the Catskills dominate, Lake Placid quietly emerges as the state’s premier basecamp, boasting more trails in the top 100 than anywhere else in New York. For cyclists craving big views and bucket-list backdrops, it’s hard to beat.
This spring, get ready to charge your phone, pack a snack and ride toward stunning views.
Most picturesque cycling trails in New York
- Blackhead Range Traverse via Kaaterskill Falls—Haines Falls
- Bull Hill, South Beacon Mountain, and North Beacon Mountain—Cold Spring
- Lake Minnewaska, Millbrook Mountain, Gertrude's Nose and Lake Awosting—Kerhonkson
- Inspiration Point and Kaaterskill Falls via Kaaterskill Rail Trail—Haines Falls
- Washburn, Undercliff, Breakneck Ridge, and Cornish Trail—Cold Spring
- Breakneck Ridge and Wilkinson Memorial Trail via Bull Hill Loop—Cold Spring
- Lake Minnewaska, Gertrude's Nose, and Millbrook Mountain Loop—Kerhonkson
- Inspiration Point and Kaaterskill Falls Loop—Haines Falls
- Kaaterskill Falls, South Mountain and North Point Loop—Haines Falls
- Escarpment Trail—Haines Falls

