Fun places to visit in Waterbury include The Rez, Green Mountain Coffee Roasters, Ben & Jerry's, Lake Champlain Chocolates, Cabot Creamery, Smuggler's Notch Distillery, Prohibition Pig, and Cold Hollow Cider Mill. Jess grew up in Waterbury and lived right next door to the Cider Mill
Take a drive up Route 100 for some lovely foliage viewing opportunities. You can start from your gondola ride in Killington, through "the valley" where you will drive through Waitsfield village (a couple covered bridges there), you'll drive by Jess's high school, up to Waterbury, and can even keep going up to Stowe. You can easily return south via the interstate.