Enjoying Vermont Dirt Roads

 Jul 2, 2025

There is no better way to kick off the Fourth of July weekend in Rutland than a post-work exploration of the local dirt. My goal for the evening was to check out the closed section of Notch Road and wander through the gravel network surrounding Jim Jeffords State Forest.

The climbing started barely a mile into the ride as I hit Killington Avenue and transitioned onto Notch Road. 

It’s a brutal Category 2 ascent—2.9 miles with a 7.5% average grade that ramps up to a punishing 18% max. It was right on that 18% kicker that I realized my Cannondale CAADx lacks the ideal low gearing for these ultra-steep Vermont walls.

At the intersection with Wheelerville Road, a sign warned that the road was closed 1,000 feet ahead. Continuing down, 

I found a second "Road Closed" sign that had clearly been used for target practice and was barely legible. Past that, the dirt road gave way to a trail descending toward the river. As the trail swung north, it narrowed to a precarious tightrope along the edge of the bank. 

This is where Tropical Storm Irene permanently rewrote the landscape on August 28, 2011. The catastrophic storm dumped up to eight inches of rain on the region, causing the North Branch of the Cold River to swell and trigger a massive landslide. 

The lower section of the road collapsed entirely and was lost to the river. Today, it’s barely passable on foot, and managing a hike-a-bike over the rough terrain made the passage feel even more adventurous.

Once through the washout, the trail opened up into a fantastic descent into the river valley, crossing the North Branch over a solid bridge. Right below, I spotted a pristine swimming hole that immediately went on my mental list for a future trout fishing trip. 

Past the bridge, Notch Road showed signs of heavy abuse from ATVs and dirt bikes, turning into a steep, curving climb of loose dirt and gravel up to Falls Road.

Falls Road is a spectacular stretch of high-quality dirt that snakes along the ridgeline, offering stunning glimpses of the Taconic Range through the trees. 

I was so caught up enjoying the views through these natural windows that I blew right past my intended turn into Jim Jeffords State Forest—the link that was supposed to connect me to Upper Cold River Road.

Before I knew it, the route degraded from a Class 4 road to a primitive doubletrack and plunged downhill. At the bottom, the road simply ended at a stream ford with absolutely no evidence a bridge had ever existed. Attempting to rock-hop across, my foot slipped on a slick stone, resulting in a classic soaked cycling shoe.

Safely across but damp, I tried a trail paralleling the stream. RideWithGPS labeled it "Moonshine Lane," but my gut told me otherwise. A quick check of a backup map confirmed the real Moonshine Lane was further away. I turned back, pointed the bike up the primitive road, and attempted to ride out. I only managed a few feet before the sheer wall forced me off the bike. 

Thus began my first official "Vermont Napoleon’s Death March"—a grueling hike up a 9% average grade that spiked to a ridiculous 21%. 

To make matters worse, the path that was supposed to connect me to the covered bridge was entirely overgrown and looked like a guarantee for a few deer ticks. Instead, I improvised, following a nearby driveway that popped me out onto the actual, maintained Moonshine Lane.

From there, I hooked onto Upper Cold River Road and started climbing again. This section is a beautiful, rolling dirt road that stretches for about four miles as it works its way up toward Shrewsbury. 

While I was working through the rollers, a couple in a Jeep slowed down and kindly asked if I wanted a tow. I thanked them but declined, asking instead if they happened to have a cold beer on hand. They had a good laugh but unfortunately came up empty-handed.

Reaching Cold River Road, I finally earned my reward: a glorious, nine-mile descent back into Rutland. The cool air of the river valley felt incredible, quickly drying out my jersey and cooling me down. 

I let gravity take over, hitting 35 mph on the steeper pitches and even tucking into the draft of a passing car for a brief, high-speed pull. 

By the time I turned onto Stratton Road and rolled back into Rutland City, the sun was setting in a brilliant blaze over the Taconic Range—a perfect end to a classic Vermont dirt adventure.