Distance: 130 miles
Elevation gain: 15, 287 ft (GPS devices vary)
Road Surface: 68% gravel; 24% asphalt; 8% Class IV
There are lots of options for a starting and ending point on this loop. For the sake of this description, we’ll start at the Barre Town Forest in Websterville. But you could start from virtually any town along the route and find options for establishing a base of operations for this lengthy and challenging route.
Your first goal is a loop around Berlin Pond, going counter-clockwise and ending up on a short Class IV section that takes you to Crosstown Road. Be careful on this descent, as it is a little hairy and traffic can be frequent even though it feels like a remote gravel road.
Once through Northfield, you’ll begin climbing up toward Bear Farm Road, which is the beginning of Waitsfield Gap, your first major climb of the day. This road becomes progressively less maintained as you go, until finally transitioning fully to a Class IV boulder track. The technical descent can be fun but conditions are highly dependent on weather, so use caution.
In Waitsfield, you’ll assault Center Fayston Road, a brutally steep climb that is almost more challenging than Waitsfield Gap due to its intense gradient. After coming back down to Route 100, you’ll head north briefly and then take the Moretown Mountain Road.
Moretown Gap is your second named climb of the day, and is a straightforward gravel climb. Not easy, but not the toughest of the day and the road is generally in pretty good condition.
Partway down the other side of Moretown Gap you’ll take a right onto the famous Devil’s Washbowl, where (legend has it) the Northfield Pigman regularly patrols. Keep your eyes peeled and your cadence high.
If you survive the Washbowl, you’ll end up back where you started the Waitsfield Gap climb, but this time you’ll head out Holstrom to find your way to Roxbury.
If you need a pit stop, there’s a general store in Roxbury just south of the Warren Mountain Road. Once you’re stocked up, head up that road to climb Roxbury Gap, a 3-mile climb that averages about 7-8% and is gravel for most of the way up. You’ll know you’ve reached the summit when you see asphalt again, and the road drops steeply down both ahead and behind you.
After descending Roxbury into Warren, you’ll follow some meandering gravel and a bit of asphalt until you find your way to the Braintree Mountain Road. This climb is a rough, unmaintained Class IV adventure. It is so rough that you will likely find it difficult to ride large portions of the ascent, so be prepared for some walking.
The road improves only slightly after the summit, and the descent is very rough, technical and challenging. Be prepared for this section to take a lot out of you, even though you’re headed downhill.
The Braintree Meeting House is a nice spot to regroup once you’ve found your way to civilization again; check out the granite statue of a catamount on the lawn.
Next, you’ll meander your way through Randolph and East Brookfield, encountering East Hill road along the way, which might be the most difficult climb of the day, despite not being a mountain pass. It is a steep, relentless gravel grind that offers little in the way of breaks or recovery.
Luckily you are rewarded with the scenic Bobbinshop Road, and a comfortable stretch of asphalt north on Route 110, before heading left onto Poor Farm Road, to climb into Washington. The top sections of this road can be rough, though not anything like Waitsfield or Braintree Gaps. A further short Class IV section will take you up onto Tower Road. From there, you’ll meander through to Lowery and LittleJohn Road, finding your way back to your point of origin.