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Harvest Festival returns for its fifth annual celebration of small-town autumn charm

Fall Comes to Downtown Bennington

By Ahmad Yassir, Vermont Country Magazine.

There is something especially inviting about autumn in Bennington. The leaves begin to turn, the air gets a little more crisp, and Downtown Bennington, with its historic buildings, walkable streets and locally owned shops, takes on the kind of small-town charm that feels almost made for a fall weekend.

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That is exactly the setting for Harvest Festival, which returns Saturday, Oct. 17, from 10 a.m. to 5 p.m. for its fifth annual celebration, produced by The Better Bennington Corporation (BBC). 

Since launching in 2021, Harvest Festival has quickly grown into one of Downtown Bennington’s favorite fall traditions. Held annually on the third Saturday in October, the event brings together more than 130 vendors, live music, food, family activities and plenty of reasons to spend the day exploring downtown.

And for anyone who has attended before, the atmosphere is part of the experience

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The festival has a way of bringing out the fall spirit in everyone, including the volunteers who make it happen. There is an unmistakable energy throughout downtown as the streets fill with people, decorations and the colors of the season.

“Fall in Vermont is truly magical and my favorite time of year. I’m excited to work alongside our team and local businesses to make Downtown Bennington a place where families and visitors can come together and make memories. It feels especially meaningful that my first Harvest Fest as Executive Director is also our fifth annual celebration, and I’m looking forward to continuing this wonderful downtown tradition,” said Ali Elwell-Zaiac, BBC Executive Director. 

A Downtown Full of Fall

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Main Street will be lined with more than 130 vendors, while School Street will become a destination for food trucks. Merchants Park will transform into the festival’s kids zone, with family-friendly activities, demonstrations and shows throughout the day.

Over at Nichols Lot, history gets a little more hands-on with a performance and battle area featuring Bennington’s Jousters, reenactors and members of Bennington’s 250th anniversary committee.

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More fall-themed activities will be announced as the festival approaches, so visitors are encouraged to follow Better Bennington’s social media updates or subscribe to its newsletter at BetterBennington.com.

Meanwhile, the Main Stage at Lucky Dragon, next to the festival dining area, will keep the soundtrack going all day with a mix of returning favorites and new performers. This year’s lineup includes Kevin Wayne & The RetroBillies, Uken Brew, Sky Alan, Beard and Glasses, and Velvet Wave.

Make a Day of It

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Harvest Festival is also a great excuse to explore beyond the festival itself.

Downtown Bennington’s independent merchants will be getting into the spirit with themed shopping, food and drink experiences and special offerings throughout the day. Because the downtown is compact and walkable, visitors can easily move between the festival and the shops, restaurants, galleries and other local businesses that make the area worth exploring year-round.

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For visitors coming from outside the area, it is the perfect kind of Vermont fall day: wander through a lively downtown, listen to local music, find something handmade, grab something delicious and take in the changing leaves along the way.

And for locals, it is a chance to celebrate the community that makes Downtown Bennington special, and support the businesses that help keep it that way.

For schedules, updates and a directory of downtown businesses to help plan a visit, visit BetterBennington.com

Vermont Country magazine

Vermont Country has a hyperlocal focus on the Green Mountain lifestyle, its personalities, events, attractions and culture. The magazine appears six times a year, designed to complement the state and four-season living. VtCo magazine is a Southern Vermont publication of Vermont News & Media.

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