15 Best Small Towns to Visit in Vermont Chester. Source: theculturetrip. Chester, Vermont. ... Woodstock. Source: flickr. Woodstock, Vermont. ... Montpelier. Source: flickr. Montpelier, Vermont. ... Brattleboro. Source: flickr. Brattleboro, Vermont. ... Lincoln. Source: flickr. ... Stowe. Source: flickr. ... Shelburne. Source: flickr. ... Grafton. Source: flickr. More items...