The best road cycling routes in Putnam County

Cycle the challenging 74-mile Hudson Valley Greenway Trail Loop, featuring diverse scenery and 2516 feet of elevation gain.

Embark on a scenic road cycling journey through the Hudson Valley with the Whaley Lake – Walkway Over the Hudson loop from Patterson. This route offers a delightful mix of serene lake views around Whaley Lake, the largest in Dutchess County, and the awe-inspiring panoramic vistas from the Walkway Over the Hudson. You'll traverse woodlands, open fields, and wetlands, experiencing the diverse natural beauty of the region.

This moderate 64.2-mile (103.3 km) ride involves 2039 feet (621 metres) of elevation gain and typically takes around 4 hours and 16 minutes. Plan for an early start to make the most of your day, especially during pleasant weather. The route primarily uses paved surfaces, including sections of the Maybrook Trailway and Empire State Trail, making for a smooth ride, though the distance requires good fitness.

The Whaley Lake – Walkway Over the Hudson loop is integrated into New York's broader statewide cycling network, utilizing parts of the extensive multi-use trail systems. It also forms a segment of the challenging 74-mile Hudson Valley Greenway Trail Loop. This route offers a fantastic opportunity to explore significant natural features and historic infrastructure within Dutchess County, New York.

This demanding road cycling route, the Bear Mountain Bridge – Lake Tiorati loop from Garrison, offers a continuous journey through the rugged Hudson Highlands. You'll pedal through dense forests, past serene freshwater lakes like Lake Tiorati, and along rugged ridges, all while enjoying sweeping views of the Hudson River and the historic Bear Mountain Bridge. The landscape transforms beautifully with the seasons, from vibrant spring greens to spectacular autumn foliage, making it a visually rewarding experience for those who love a challenge.

Planning your ride requires attention to detail, as this is a difficult 59.3-mile (95.5 km) loop with 4956 feet (1510 metres) of elevation gain, taking about 5 hours and 11 minutes. Garrison is a convenient starting point, especially if you're arriving via bike-friendly Metro-North train services. Be mindful of legal restrictions; cycling along or across certain sections of the Palisades Interstate Parkway and Route 6 is not permitted, so ensure your planned route avoids these areas.

This loop is a notable and rewarding experience for road cyclists, combining challenging climbs with the natural beauty of Bear Mountain and Harriman State Parks. The Bear Mountain Bridge itself is a historic marvel, offering dedicated pathways for safe passage and broad views. On clear days, the panoramic vistas from points like Perkins Memorial Tower on Bear Mountain can even stretch to the distant New York City skyline, making the effort truly worthwhile.

Embark on a scenic road cycling adventure along the Maybrook Trailway loop, where you'll glide through quiet woodlands and past picturesque bodies of water like Whaley Lake. The route offers a delightful mix of the smooth, generally flat rail trail terrain and the more engaging, challenging hills found on the Dutchess County backroads. This moderate 26.5 miles (42.6 km) journey, with its 1176 feet (358 metres) of elevation gain, provides a varied and rewarding experience for cyclists seeking both tranquility and a good workout.

To plan your visit, you can park conveniently near the Cranberry Mountain Wildlife Management Area. Be aware that services are limited along the Maybrook Trailway itself, so come prepared with water and any other necessities for your 1 hours and 54 minutes ride. The trail's connection to the broader Empire State Trail network also offers excellent opportunities for longer rides or exploring other sections.

This Maybrook Trailway loop is a fantastic way to experience a piece of New York's history, as it repurposes a former two-track freight line, allowing you to traverse areas once only accessible by rail. The trail's design means you'll encounter unique natural features like rock cuts and iron truss bridges, providing a distinct perspective on the rural landscape. It's a prime example of how rail trails offer accessible and scenic viewpoints for outdoor enthusiasts.