Upper Greenwood Lake – Wawayanda Creek loop from Bloomingdale

If you're looking for a serious challenge on two wheels, the Upper Greenwood Lake – Wawayanda Creek loop from Bloomingdale is one of those road cycling routes that truly tests your mettle. This difficult 63.0-mile (101.4 km) ride packs in a hefty 4263 feet (1299 metres) of climbing over roughly 5 hours and 10 minutes, making it perfect for experienced cyclists seeking a rewarding day in the saddle.

What to expect on Upper Greenwood Lake – Wawayanda Creek loop from Bloomingdale

As you tackle this challenging road cycling route, you'll journey through a diverse landscape that shifts from the serene views of Upper Greenwood Lake, a 400-acre man-made lake nestled in mountainous terrain, to the rural charm of the Wawayanda Creek area, with its farms, woods, and glimpses of the Rockaway River. Expect mostly well-paved surfaces, but be prepared for some unpaved and difficult segments, especially on the eastern side of Greenwood Lake where tree-lined roads feature steep ascents and descents. This ride demands very good fitness, offering expansive scenic vistas as it extends into parts of New York.

Planning your visit

This loop is the most popular road cycling route originating from Bloomingdale, so while specific parking details aren't provided, it's wise to arrive early, especially on pleasant days. The route is best enjoyed when conditions are dry, given the potential for unpaved sections. Always carry enough water and nutrition for the full 5 hours and 10 minutes, as amenities can be sparse in the rural stretches.

Trail details

• Distance: 63.0 miles (101.4 km)
• Elevation gain: 4263 feet (1299 metres)
• Difficulty: difficult
• Estimated time: 5 hours and 10 minutes