When Sarah and her husband Ben Wood opened Otter Creek Bakery in Middlebury in 1986, Sarah Wood’s car — a 1961 green VW Bug endearingly named “Pippin” — was their business’ main delivery vehicle, fondly recognizable to many people in town at the time. Pippin’s bright color and eye-catching flower spinner attached to its side separated it from the crowd of 75 antique cars lined up on Main Street for the second annual Middlebury Car Show and Fall Festival last weekend.
The Festival took place on Sunday, Oct. 15 from 10 a.m – 3 p.m. on Main Street and Triangle Park in downtown Middlebury and was jointly organized by the Better Middlebury Partnership and the Addison County Chamber of Commerce. Open and free to the public, the event included not only the featured cars but also over 50 vendors selling food and merchandise, live music, a silent auction, a raffle and activities for children.
Last year’s inaugural Festival and Car Show received positive reviews from local businesses, attendees, vendors and car owners, encouraging the organizers to bring the event back again this year, according to Phil Summers, executive director of the Addison County Chamber of Commerce. The event’s attendance rose from approximately 2,500 to 3,000 people from last year to this year, he wrote in an email to The Campus.
Participants in the car show registered in advance on a first-come, first-serve basis on the Addison County Chamber of Commerce website until the 75-car limit was reached. Each participant entered information on for a sheet of paper with their name, hometown and their car’s make and model to display on their dashboard during the show.
Viewers could make their way up Main Street to peruse the car selection and use the designated number on each sheet of paper to place a vote for a preferred winner under multiple categories: “Best of Show,” “People’s Choice” and “Best of Decade,” allowing for one winner from each decade between the 1910s and 2010s.
While last Sunday was Sarah Wood’s first time bringing Pippin to a car show, other participants were seasoned car show participants. Huntington, Vt. resident Daniel Steadman brought his black 1946 Special Deluxe Plymouth to the show both years. Steadman said that he fell in love with the car when he first saw it six years ago and has flaunted it at several car shows in Vermont and New York in the past three years with his brother, whose car neighbored his in the display row.
“The people you meet, the stories you hear and the comments you get make it worth it,” Steadman told The Campus. Steadman said he often runs into the same people at multiple car shows and remembers previous conversations he had with them, sparking connections and friendships.
Addison, Vt. resident Dennis Benoit’s 1956 Belair Chevrolet won the “Best of 50’s” category at last year’s car show and festival, his medal prize still hanging from his rear view mirror. According to Benoit, the best part of bringing his car to shows is letting people sit in it and touch it.
“It’s an old car,” Benoit said. “It’s meant to be enjoyed.”
Bruce Waterworth, a Rutland, Vt. resident originally from England, brought his red 1972 Lotus Europa with a picture of Queen Elizabeth taped to the passenger seat window and English flag-patterned carpeting on its front seat floor. The Lotus only comes out for special occasions like this show, according to Waterworth.
Waterworth was not alone in his car decoration pursuits. Two large stuffed cows sat in the backseat of one vehicle, and another had old Smith Indian Fire Pumps and vintage Vermont firefighter tools on display in the back. The show was an opportunity for creativity and for the owners to share what they find most interesting about their vintage cars, exchanging stories and relaying their vehicles’ unique histories.
Townline Grill, The Rollin’ Rooster and Chim Chimney Bakery all served out of food trucks, and small businesses sold rainbow ice, prints, clothing, popcorn cookies, jewelry and other goods from tented stands, reminiscent of Middlebury’s Summer Market. Local rock band Sanctuary, as well as Vermont-based Ska and Reggae-inspired band Soulstice performed at the Middlebury Green Gazebo during the festival.
The festival’s vintage sponsor was Painting With Purpose, a professional Burlington-based painting company that hosted a silent auction at the event for Adirondack chairs. Other sponsors included Berkshire Hathaway Homeservices, IPJ Real Estate and Silver Maple Construction.
In an interview with The Campus about last year’s festival, executive director of the Better Middlebury Partnership Karen Duguay expressed hope that the Car Show and Fall Festival would bring new patrons to local businesses and economically stimulate the town. With attendees crowding around Otter Creek Bakery to line up for baked goods and outside Little Seed Coffee Roasters for hot drinks, the event provided extra support to the community for the second year in a row.
Madeleine Kaptein '25.5 (she/her) is a managing editor.
Madeleine previously served as a staff writer, copy editor and local editor. She is a Comparative Literature major with minors in German and Art History. In Spring 2024, she studied abroad in Mainz, Germany, from where she wrote for the Addison Independent about her host country. In her free time, she enjoys journaling, long walks and runs, and uncomplicated visual arts projects.
