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HomeHikingExplore Vermont's Long Trail Side-to-Side: A Hiker's Adventure

Explore Vermont’s Long Trail Side-to-Side: A Hiker’s Adventure


Vermont’s Long Trail is the oldest National Scenic Trail in the United States. It runs 272 miles from the Massachusetts-Vermont border north to Vermont’s border with Canada. It’s a great trail to thru-hike or section hike. I finished hiking the Long Trail end-to-end in 2008, but I wanted to return this summer and hike what’s known as a Long Trail Side-to-Side, which requires hiking all the side trails that intersect the Long Trail.

The Long Trail Side-to-Side list includes 88 trails, totaling 166 miles.  Of course, the distance you have to hike is much longer than that because many of the hikes are out-and-backs, where you have to retrace your steps to get back to the trailhead where you left your car. I’m trying to do as many trails as I can as backpacking loops that incorporate sections of the Long Trail proper, but there aren’t many places where that’s possible, given the dispersion of trails on the list.

GMC Side-to-Side Spreadsheet
GMC Side-to-Side Spreadsheet (download here)

The Side-to-Side list is not without its share of challenges. The trails are not contiguous and are widely dispersed along the length of the Long Trail, so it takes some effort to drive to their trailheads to hike them. Many of the trailheads are also on seasonal forest service roads that are either closed or snowed over in winter, significantly shortening the season they can be hiked. Plus, hiking during mud season (May) on trails maintained by the Green Mountain Club is frowned upon, shortening the hiking calendar even more.

That said, it’s a fun list to hike because it takes you to all the small towns along the west and east sides of the Long Trail from the state’s southern border to Canada in the north. It’s a great way to tour the state and drive down many unpaved roads in the middle of nowhere if that kind of adventure appeals to you. I must admit, I do enjoy it myself!

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. That spreadsheet is very similar to the official White Mountain Guide Redlining Spreadsheet posted in the White Mountain Guide Redlining Facebook Group that hikers use to keep track of the 664 (1480.2 miles) trails in the Appalachian Mountain Club’s White Mountain Guide.

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. Regarding digital navigation, I use the AvenzaMaps app and purchased the GMC’s Long Trail Map for use with it: it is way better than GaiaGPS for this trail system.

I’ve just started the Side-to-Side list, but I’ve found it to be tremendously fun so far and hope to complete it before the end of 2024.

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