Many hikers have dreamed of hiking Vermont’s legendary Long Trail. Stretching 272 miles from Massachusetts to the Canadian border—crossing the Green Mountains along the way—completing the trail is one of the Northeast’s greatest hiking feats.
But hidden alongside that famous trail is another hiking challenge that many hikers probably haven’t heard of; an adventure that might actually provide a more thorough glimpse into what makes Vermont such an incredible hiking destination.
It’s the Long Trail Side-to-Side Challenge, a quest that asks: What if you hiked every blue-blazed side trail connected to the Long Trail?
A Different Kind of Hiking Challenge
All along the Long Trail, dozens of side trails branch away from the main route, leading to scenic mountain summits, quiet ponds, waterfalls, and other beautiful places that many Long Trail hikers never experience.
The Green Mountain Club’s Side-to-Side Challenge encourages hikers to explore every one of them.
That means hiking a total of 88 designated side trails covering 166.1 miles. While many of the trails are there to simply access the Long Trail, others are worthwhile destinations on their own, taking hikers to some of Vermont’s lesser-known natural treasures.
You don’t need to be an advanced thru-hiker or endurance junkie to take on this quest. The Side-to-Side Challenge is ideal for day hikers and weekend adventurers. The side trails range from just 0.1 mile up to the Lye Brook Trail, which is just under 10 miles. But the bulk of the trails are just a few miles at most.
The Green Mountain Club formally created the Side-to-Side Challenge in 2006, after years of hikers informally taking it on. According to the club’s records, only 71 hikers have officially completed it since then.
For comparison, more than 8,000 hikers are registered Long Trail End-to-Enders.
The trails offer hikers a wide variety of scenery and terrain, from easy, peaceful paths to rocky, challenging hikes. Among them, the side trails on Mount Mansfield are notable for their rugged difficulty. Trails such as the Subway, Canyon, Canyon North, and Canyon North Extension include fun and challenging scrambles through caves and crevices.
A few of the side trails are actually former historic routes of the Long Trail, rerouted for various reasons. These include the Sherburne Pass Trail from Pico Peak to Route 4, and the Duck Brook Trail in Bolton.
Side-To-Side Certification
The Green Mountain Club recognizes hikers who complete every designated side trail with their Side-to-Side certification.
Hikers record when they hike each trail using the club’s official tracker. Once all 88 trails have been completed, hikers can submit their tracker for certification.
Successful finishers receive:
- A Long Trail Side-to-Side certificate
- A commemorative rocker patch and Green Mountain Club patch
- Recognition in the Green Mountain Club’s Long Trail News
- A complimentary one-year Green Mountain Club membership (for first-time members)
Because the trails are scattered from the Massachusetts border all the way to Canada, planning becomes part of the adventure.
Chloe Miller, Communications Manager for the Green Mountain Club, said hikers should be prepared to do a lot of logistics planning to access all the trails. She said hikers end up hiking far more than the 166 total miles because of all the out and backs.
The same goes for driving to all the trailheads. In fact, Miller said many hikers say they enjoyed exploring different backroads and parts of Vermont as part of the challenge.
The Green Mountain Club’s Long Trail Guide and Long Trail Map provide detailed trail descriptions and directions to trailheads, allowing hikers to piece together reasonable hiking itineraries.
“There’s no one right way to do it,” said Miller. “The Side-to-Side challenge has countless ways to go about it.”
Learn more about the Green Mountain Club’s Long Trail Side-to-Side Challenge.
