The best road cycling routes around Dover Plains

The Wassaic Rail Station loop from Wassaic offers a delightful and easygoing road cycling experience, primarily along the well-maintained asphalt of the Harlem Valley Rail Trail. As you pedal, you'll be treated to a continuous tapestry of bucolic rural landscapes, winding through farmland, shaded woodlands, and past wetlands and creeks. Keep an eye out for horses, sheep, and apple farms, and enjoy the peaceful atmosphere of this scenic Dutchess County route.

Planning your ride is straightforward, as the trail conveniently starts right at the Wassaic Metro-North train station, making it an excellent option for those arriving by public transport from New York City. Parking is also available at the station. This 15.4-mile (24.7 km) route, with a gentle 420 feet (128 metres) of elevation gain, is rated easy and typically takes about 1 hour and 18 minutes, making it perfect for a relaxed outing. Consider visiting during the warmer months to fully enjoy the amenities in towns like Millerton, which offer cafes and restaurants.

This route is a prime example of a successful rail-to-trail conversion, built upon an abandoned rail alignment, and serves as an intermodal hub connecting train travel with cycling adventures. The Harlem Valley Rail Trail itself spans over 26 miles, connecting Wassaic to Hillsdale, with ongoing expansion efforts. This particular loop provides a taste of the trail's charm, offering a family-friendly and accessible way to explore the picturesque countryside.

The Wassiac Bridge over a Creek – Wassiac Rail Station loop from Kent offers a demanding road cycling experience, diverging from the usual flat rail trail to present a true challenge. You'll navigate a diverse landscape featuring wooded areas, open grasslands, and active farmlands, with scenic views of the Taconic Berkshires and multiple crossings of Webatuck Creek. This difficult 68.4-mile (110.1 km) route, with its 2970 feet (905 metres) of elevation gain, is designed for cyclists who relish a significant physical effort over roughly 4 hours and 58 minutes.

For planning your ride, the Wassaic Rail Station provides convenient access, especially if you're arriving by Metro-North train. While the area boasts amenities like farmers' markets and restaurants in towns such as Millerton, ensure you carry enough water and nutrition for this extensive loop. The best time to tackle this route is during mild weather, as the length and elevation can be taxing in extreme conditions.

This loop stands out as one of the more challenging road cycling routes in Dutchess County, offering a comprehensive tour of the region's varied terrain. Unlike the predominantly flat Harlem Valley Rail Trail, this route incorporates substantial climbs, providing a different perspective on the area's natural beauty and rural charm. It's a notable option for those seeking to push their limits beyond typical rail trail rides.