Roxbury Gap – Rochester loop from Randolph

The Roxbury Gap – Rochester loop from Randolph is one of Vermont's most challenging road cycling routes, a difficult 57.8-mile (93.0 km) journey with a staggering 4186 feet (1276 metres) of elevation gain, typically completed in just under 5 hours. This route is perfect for experienced cyclists seeking a demanding ride through the Green Mountains, testing both endurance and bike handling skills.

What to expect on Roxbury Gap – Rochester loop from Randolph

This loop is a true test of grit, taking you through rural landscapes with significant elevation changes and picturesque views. You'll tackle the formidable Roxbury Gap, known for its unpaved sections that turn to dirt for part of the climb and descent, making it particularly challenging on standard road tires. The descent from Roxbury Gap is noted as "pure dirt," adding a unique technical element to this road cycling route. Following this, you'll face Rochester Gap, another substantial climb with sections reaching 13-15% grades, all while enjoying streams, forests, and the diverse topography of the Green Mountains.

Planning your visit

Given the difficult nature and unpaved sections of Roxbury Gap, ensure your bike is equipped to handle varied terrain, or be prepared for a challenging ride on narrower road tires. The route starts from Randolph, and while specific parking details aren't provided, Randolph offers a convenient access point. This loop is best enjoyed by cyclists with very good fitness, ready to commit about 5 hours to an arduous yet rewarding adventure through the Vermont Gaps.

Trail details

• Distance: 57.8 miles (93.0 km)
• Elevation gain: 4186 feet (1276 metres)
• Difficulty: difficult
• Estimated time: 4 hours and 59 minutes