The Green Mountain Clubs’ Long Trail runs 272 miles from the Canadian Border to the Massachusetts Border, running north to south. The Long Trail Side-to-Side trail list includes all the trails that lead to the Long Trail from the east and the west. I hiked the Long Trail proper in 2008 and just finished the Side-to-Side list last week (in 2025).

The Side-to-Side list is a lot of fun to hike and includes 88 trails that span 166.1 miles. I’m not exactly sure how many miles I had to hike to finish this list, but it was a lot more than 166.1 miles, since many are out-and-back hikes and day hikes, with a half dozen backpacking trips sprinkled in.

The trails themselves are distributed across the state and provide a great way to visit the many towns, state parks, and national forests that border the Long Trail, which runs up the central spine of the state. Some of the trails are in need of a little TLC, but they’re in pretty good shape for the most part. Finding their trailheads can be a bit of a challenge, since they’re often in the middle of nowhere and down a dirt road. That kind of adventure appeals to me, though.

The one thing that surprised me was how many people hike these side trails, particularly local Vermonters. These trails serve as on-ramps to the Long Trail for people who aren’t thru-hikers, and their value to the Green Mountain Club can not be overstated. I hope that the club will put as much effort into protecting them as they have with the Long Trail corridor itself.

The list of Side-to-Side trails that must be hiked is on the Green Mountain Club website, which also publishes a spreadsheet for tracking progress. In terms of maps, you’ll want a copy of the Green Mountain Club’s Long Trail Map and a Delorme New Hampshire/Vermont Gazetteer (road atlas), which is very helpful for finding the trailheads. The Trailfinder website is also quite helpful for directions to trailheads. Regarding digital navigation, I used the AvenzaMaps app and purchased the GMC’s Long Trail Map for use with it. GaiaGPS’s coverage of Vermont trails is worse than abysmal.

When you finish the Side-to-Side list, your name gets published in the Long Trail News magazine that the GMC sends out quarterly. Non-GMC members get a free 1-year membership, a certificate recognizing the achievement, and a sew-on patch.

If you’ve already hiked the Long Trail, the Side-to-Side list is a great way to reacquaint yourself with the Long Trail System and keep the memory of it alive.

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