Catskill Mountain House Road

The crumbling remains of this mountain resort road climb 2,000 feet up the Catskill Escarpment to the site of the famous Mountain House, where wealthy New Yorkers once came to escape the city. The final three miles require serious commitment — loose shale, washouts from decades of abandonment, and grades that’ll have you wondering if your transmission will hold. The payoff comes at the ruins themselves, where you can still see foundation stones and the clearing where the grand hotel once commanded views across the entire Hudson Valley.

This is technical 4WD territory with mandatory low-range and strong brakes for the descent. Rock sliders highly recommended for the loose shale sections. Spring and fall offer the best conditions and clearest views, though snow can linger into May at elevation. No camping allowed in this day-use area, but you’ll have earned one of the most dramatic overlooks in the Northeast. The same vista that inspired the Hudson River School painters is yours for the price of some undercarriage scrapes.