Middlebury Car Show & Fall Festival

Triangle Park Main St. and Merchants Row, Middlebury

Join us for the 5th Annual Middlebury Car Show & Fall Festival. Main Street will close to welcome 75 vehicles for a day of family-friendly fun in the heart of downtown. Enjoy food trucks, 30+ vendors, music, children’s activities, and more while exploring one of Vermont’s most vibrant downtowns. Brought to you by the Addison County […]

Free

39th Annual Ripton Ridge Run

Former Ripton Elementary School 753 Lincoln Rd., Ripton

5K run, 10.5K run and non-competitive 5K Fun Walk on scenic roads. Registration fee includes long-sleeved t-shirt, lunch and raffle. Hosted by Friends of Ripton Students Inc., this fundraiser benefits Ripton students of all ages. Register online before Oct. 10 or in person from 11 a.m. – noon on race day.

Harvest Music Series: Bird Mountain String Band

Champlain Orchards 3597 VT-74 W., Shoreham

Bird Mountain String Band: Family old-time and bluegrass band from a small farmstead in Vermont. Join us at the orchard for a day of apple picking and great music! The Cider Garden will also be open for full cider pours and tasting flights, cider slushies, charcuterie boards, s'mores, soft pretzels, and so much more. Gather […]

Live Music: Justin Lapoint

Yates Orchard 1074 Davis Rd., Hinesburg

Bring a picnic, enjoy a Dreamee and relax in the orchard with singer-songwriter Justin Lapoint’s blend of folk, bluegrass and blues.

Free