"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."
"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."
"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."
Holland Bikes analyzed over 5,000 cycling trails across New York State to identify the most picturesque routes for the 2026 Trail Index. The ranking evaluated trails based on ratings, popularity, and photo frequency, with top-scoring trails earning "picture perfect" scores of 90 or higher. The Blackhead Range Traverse via Kaaterskill Falls leads with a 94.14 score, featuring a two-tiered waterfall in the Catskill Mountains. Other highly-ranked trails include Bull Hill in Cold Spring with Hudson Highlands views and the Lake Minnewaska-Millbrook Mountain route in Kerhonkson. A notable trend shows riders prefer shorter loops around scenic features like waterfalls and lookout points over longer endurance routes, with high-scoring trails averaging 3.25 photos per kilometer.
Read at Time Out New York
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