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Woodbury Fall Fest Set for October 1

New England Knockerball will be at the Woodbury Fall Fest again this year.

New England Knockerball will be at the Woodbury Fall Fest again this year.

WOODBURY – It’s almost that time again! The third annual “Woodbury Fall Festival: A Meander Down Main Street”, created by WOW, What’s On in Woodbury, will take place on October 1 from 2pm to 6pm along Main Street South, from the post office to Canfield Corner.

According to Woodbury Parks and Recreation Director Jenifer Miller, this year’s Fall Fest will have all the features visitors have come to expect from past festivals: Food trucks, local vendors, and entertainment. At the North Green, the annual “Taste of Woodbury” will feature local restaurants offering samples of their food, and, of course, beer and wine will be available. The highlight of the day will be the annual Pumpkin Derby, now in its third year.

Over sixteen food trucks will line both sides of Main Streets during the Fall Fest, where visitors can find all types of fare. Besides burgers, BBQ and baked goods, two favorites will be setting up to serve: The award-winning G Monkey Mobile will offer 100% vegan and organic cuisine, and Tipsy Cones will be scooping out ice cream and sorbets inspired by cocktails and cordials. Two local vendors will also be making an appearance: El Camion will bring their popular tacos, and new to the festival this year, Green Eggs and Hamburgers, a joint effort between Woodbury Farm Market and John’s Café, will be cooking burgers, hot dogs, and dishing out salads and quinoa.

Once again, according to Miller, support for Fall Fest by local businesses has been great. Nearly one hundred vendors and non-profit organizations have taken space along Main Street. Many will be selling selections from their shops, or providing a look at what they offer. Boy Scout Troop 480, sponsored by St. Paul’s Episcopal Church, will have an inflatable set at the Post Office Green, and What’s On in Woodbury will be offering a sneak peek at upcoming WOW events.

This year, entertainment will be provided from two stages. Among the performances scheduled is favorite local band “Root Six”, in their third appearance at the Fall Fest.

“It’s been great watching this festival grow over the years to a major event,” says band member Frank Hallenbeck. “Since we’re all from the extended Woodbury area, we enjoy playing in front of our friends and family, and at the same time, supporting our community.” Other performers include Blues Alley, Gorja, Maia Dobbs, GP2, Tailson, and the Dr. Steve Band.

Starting at 2 pm, the North Green opens the Taste of Woodbury, where local restaurants offer coupons, menus, and, in some cases, samples from their menus. This has been a popular attraction at past Fall Fests, and it’s hoped that this year will see the same crowds as in previous years.

For the adults, Oxford’s Black Hog Brewing and Woodbury’s own Walker Road Vineyard will be participating at the North Green with their locally produced beer and wine. Attendees will be able to purchase tickets from the fair organizers to sample the beverages on-site, and proper ID is required.

The highly anticipated “Pumpkin Derby”, sponsored by the Woodbury Business Association, is planned to kick off at 4 pm from the top of School Street. Residents are invited to enter the derby by creating a decorated pumpkin or gourd on wheels and bringing it to Fall Fest. Entrants will be raced against other pumpkins, with a prize for the fastest pumpkin in the race. A prize will also be awarded for the most creative pumpkin. This is a popular event with kids and those young at heart of all ages. The original Woodbury Fall Fest in 2015 held the first “Pumpkin Derby” in the state.

The WOW Committee reminds everyone that Main Street will be closed to all traffic between Route 47 and Judson Street starting from 1pm until after the event, and a letter informing residents and businesses along the Fall Fest area has been sent. Free parking for all is available at Mitchell School and Woodbury Middle School.

WOW is a joint effort between Jenifer Miller from the Woodbury Parks and Recreation department, Loryn Ray from the Woodbury Senior Center, and Marla Martin from the Woodbury Public Library. TD Bank is the main sponsor of the Third Annual Woodbury Fall Fest, with support from the Connecticut Community Foundation.

For more information, contact or visit their website,

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