The Long Trail is the oldest long-distance trail in the United States, constructed between 1910 and 1930 by the Green Mountain Club. It runs 272 miles through whole length of Vermont. It starts at the Massachusetts state line, and runs north along the main ridge of the Green Mountains to the Canadian border (near North Troy, Vermont). The first 100 miles coincide with the Appalachian Trail all the way to Maine Junction near Sherburne Pass where the AT branches off.

The Long Trail traverses almost all of the Green Mountains' major summits, including (from south to north) Glastenbury Mountain, Stratton Mountain, Killington Peak, Mount Abraham, Mount Ellen, Camel's Hump, Mount Mansfield, and Jay Peak. It served as the inspiration for the Appalachian Trail as it was on a hike on the Long Trail's Stratton Mountain that Benton MacKaye conceived the idea of the Appalachian Trail

Anyone who has hiked the whole AT has already completed the southern 100 miles (over one-third) of the Long Trail, so there is a strong temptation to finish it.

In August 2002 I set off with my friend Buckeye who I had met on the AT. In planning the hike we had a logistical challenge that we didn't have on the AT. The first nine days between Sherburne pass and Jonesville there is no reasonable possibility of resupply. Neither of us wanted to start off with nine days worth of food so we resorted to a creative solution of leaving a food cache in the woods half way at Lincoln Gap.