Guilford

One of the first towns settled in what would become Vermont, Guilford was chartered in 1754 under a New Hampshire grant and saw its first permanent settlers arrive in the early 1760s. The town's location in southeastern Windham County, near the Massachusetts border, placed it at the center of early disputes between New Hampshire and New York over territorial claims. In the turbulent years of the Republic of Vermont, Guilford was a hotbed of resistance to Vermont authority, with some residents preferring to remain under New York's jurisdiction.

Today Guilford is home to about 2,150 people spread across a hilly, largely rural landscape. The town hosts the annual Guilford Fair, one of the oldest agricultural fairs in Vermont, which has brought the community together for over a century. The Broad Brook Community Center and the town's historic meetinghouses anchor social life.

Guilford's selectboard and town meeting continue the tradition of local self-governance. Given the town's history of fierce independence — even from Vermont itself — the annual gathering of citizens to debate and decide carries a particular resonance here.