Long

Classic paved and unpaved Gap A-Ride with some challenging but rideable class IV on Rochester Gap and in Middlebury and Lincoln. Spectacular views on the Braintree Hill finish after Roxbury Gap. Stores available at mile 39 (Ripton), mile 60 (Jerusalem), and mile 73 (Waitsfield). Definitely recommend lots of water/carbs, wide tires, negative gear ratios, and climbing legs.

A monster gap ride. This route is mainly dirt roads linking many of Vermont's Gaps (Randolf, Brandon, App, Moretown) and remote byways. There are a half dozen sections of challenging but mostly rideable class IV. There are stores at mile 39 (Ripton), mile 60 (Jerusalem), mile 73 (Waitsfield), mile 84 (Moretown) and mile 100 (Northfield). Definitely recommend lots of water/carbs, wide tires, negative gear ratios, and climbing legs for this one!

This route features a mix of surfaces, trying to respect early dirt road conditions.  Less respect shown to early legs.

There is Huggets Market at mile 42.7 for fuel.

This is a challenging and scenic cycling route covering 112.09 miles with a total elevation gain of 13,736 feet. It's designed for cyclists looking for a demanding ride featuring multiple significant climbs and descents across gravel and paved terrain.

Key highlights of the route include:

Deep rooted in Orange County, VT, this route is rugged. A recommended tire size of 45mm or larger, alongside climbing gears is mandatory for a good time. 

There is a small section of single track (hike a bike for most) on Wrights Mtn, that is well worth the views. This route was built for those looking to get filthy, and doesn't showcase much pavement. 

From Vermont Backpackers

OVERVIEW: A challenging and rewarding mountain bike tour through the pastoral beauty of the Upper Valley. This route takes you south from Woodstock to Mount Ascutney and up and across its broad flank before heading back north. In between, you’ll ramble over hills and into valleys on twisting tree-lined back roads and trails. Farmside views and swooping trails are the primary rewards for the plentiful climbing on this route.