BENNINGTON —
Everyone was gathered for Mayfest 2025 and, despite the weather, the atmosphere was lively and fun, children were unhampered by the drizzle, and adults mingled to laugh, catch up, and converse with friends.
The Merchants Park splash pad was located very near to the Thompson Stage, where balloon twisting, a petting zoo with baby animals, and performances geared toward children kept little kids occupied for hours. Performances were conducted by BTC Entertainment, the Cross Over Cloggers, and the Monument Arts and Cultural Center. In addition, there was a building workshop and a microgreen planting workshop at the location. Between the magician performances and the monarch butterfly stilt walker, there was a lot to engage kiddos and was offered free of charge.
Around the corner on Main Street, Mayfest also had numerous face painting tents catering to a steady flow of young patrons. Separate from the designated Children’s Area in Merchants Park, the face painting was included with the vendors.
“We just got here,” said Desiree Williams, who was out with her significant other, Josh, their children, and family. The group was excited to be at Mayfest, and the children’s faces were already painted. Harley Jacobs, also out with his young family, voiced the same, “It’s been a long time. We haven’t been here since COVID, but we’re real excited. Real excited – especially the kids, you know? They love this type of stuff. And, you know, she’ll shop all day.” Jacobs indicated his wife, laughing, who was juggling a toddler, a diaper bag, a purse, and more than a few shopping bags while Jacobs soothed the fussing baby in the stroller. Two other children, an older child and cousin, were looking around.
According to Jeanne Mintrone, executive director of the Better Bennington Corporation (BBC), one of the reasons that she felt the town was seeing more young people and young families at this year’s Mayfest event was the introduction of the designated and free Children’s Area. “There’s just a lot of stuff going on. I’ve done the designated Children’s Area since I started and I’ve been trying to kind of do two different things for kids each festival. Last October we had raptors and a raptor show for Harvest Fest.”
Mintrone spent most of the day scurrying from vendor to vendor in the general operations and management of the event. “It was a slow start, and it was really raining when we set up,” said Mintrone, whose feet in the late afternoon were still soaked from the initial morning downpour. Putting on an event like Mayfest is a major undertaking, she noted. However, despite the inclement weather at the start of the day, she said that only 10 vendors cancelled.
With over 140 vendors booked for the event, that was rather impressive, Mintrone thought. “It was one food vendor, and the rest were craft vendors. But, I’m really pleased with the turnout, especially considering what we had going on. I mean, it’s cool and it’s raining, but people are waiting like an hour for mac and cheese over there.”
People were waiting in long lines at the nearly one dozen food trucks, with many seemingly embracing the weather and in fine spirits. As the rain fell, some could be seen laughing and conversing with friends and acquaintances, or simply waiting in line and tapping their feet or swaying to the live music on the corner. One pair had given up on the umbrellas altogether, and were simply using them as walking sticks.
Braedon Thompson and his girlfriend Mavis, who has family in the area, made the trip to Bennington from where they live near Albany. “We didn’t have anything else today, so why not,” Thompson said.
They were both considering whether to continue waiting for the fare from The Mac Factor food truck, or switching over to Mama Maria’s Gyros or Cousins Maine Lobster. “I mean, I could go for a lobstah roll,” joked Thompson, shoving his hands in his pockets and hunching his shoulders to the rain. The Mac Factor was a favorite, Thompson said, and one of the reasons that they pair decided to take the drive. Thompson’s “go-to” was the buffalo chicken mac and cheese with both ranch and blue cheese, but his girlfriend preferred something called the bacon mac burger – with mac and cheese inside the toasted bun – but, Thompson added that she always ended up eating some of his anyway.
With the weather clearing briefly in the early afternoon, Bennington local Bee Arcodia was more interested in perusing and browsing through the vendor stalls . Out with a friend, she was interested in finding shops with some handmade jewelry – and there were plenty. From Theodessa Designs with unique jewelry created out of mid-century flatware, to the numerous tents filled with the more traditional jewelry boutique-ware, Arcodia felt that she was sure she’d find numerous baubles to her liking.
Quirky fun was everywhere — a storm trooper with a backpack on one side of the street, a stilt walker adorned as a monarch butterfly on the other. A magician jumped out into the street, waving jazz hands at the audience. The charade continued until a rabbit was pulled from a hat.
The event hosted numerous performances on Main Street at several different locations. Outside of Knapps Hobby Shop, The Devlin's, Homefried Valentines, and Anne Marie Jarvis performed live music on a raised stage throughout the day. While the first two groups were able to use the speakers, the rain made it impossible for the latter performers — who still managed to entertain and add to the overall ambiance of the event.
In the mid-afternoon, the Ukulele String Ensemble & Woodwind Trio played a number of “oldies but goodies” outside of Bennington's Lucky Dragon restaurant. The group followed on the heels of performances from Cosby Gibson & Tom Staudle and All Ten & John. Jamie Ransom rounded out the live music performances at the location. However, just up the street on the Nichols Stage were the performances of J2, It's Magic by Doug Eash, Hidden Angel, and Immune Friction.
In the vendor tents, Rockwood Studio was selling out of the heart mugs and woodworkers Todd Rogers II and Richard Addison — both makers of fine cutting boards — were turning over available stock. Gay Jenson of Kangaroo Dogs turmeric and anti-inflammatory pet products was chatting with visitors to her tent, Carol Currran of Barred Owl Bags was showing off her handmade quilted products while Jeremy O’Neil of Greenhouse Maple and the folks at the Willis Towne Farm were chatting with customers.
Nearby, Cassie Meiswinkel of Sole Connection Farm in Arlington and Lindsey Pszwaro of Panacea Herb Farm in Shaftsbury were explaining their tinctures and products to individuals. The folks at Goodhue Bakery were nearly sold out of product, and were making gentle fun of each other’s height with John Leray Jr. being more of the giant to Chantel Goodhue’s average height. Ken Carlsen was talking geology and teaching about gems and minerals at his tent, and Jim Hulett of Hulett Farms was manning the booth that contained the lotions, soaps, and haircare bars made by his wife Selina Ferrandino. “She’s the creator; I’m more of the business guy,” Hulett explained as he showed off the lotion bars to a gentleman with dry hands.
Back at the food trucks, a heavily manned crew at Hound Dogs of Manchester was cranking out the dogs, fries, and other specialty foods. “They have the best — the best — onion rings,” exclaimed an excited Jazmine Stuart, who was out with her elderly mom who lives in the Hoosick, New York area, “She loves them. We drive over to Manchester to get them, and make a treat of it. Couldn’t miss coming out today, though. Love Mayfest — it’s just awesome.”
Neil of Hound Dogs said that the weather hadn’t really dampened the crowd, as far as he could tell, “It’s been really good for us, good from this point of view, but I don’t know if we’re a good barometer for the whole event.”
Behind the scenes, young gentlemen from the Civil Air Patrol helped to keep the streets clean and tidy, “We’re just going around, picking up trash and helping out,” said the young Sergeant Griffon Lepage, as he explained what the Civil Air Patrol was. “We’re an auxiliary of the Air Force, so the main focus is search and rescue.” Lepage said that he believed that the youngest a person could be to join the Civil Air Patrol was “12 or 13,” but that there was a chapter local to the Bennington area.
Mintrone added that the crowd size was reassuring, even with the weather. People, she thought, looked forward to the Mayfest event, no matter what, “This is a signature event,” said Mintrone, looking around and beaming. “It’s been going on for 38 years. People know that it goes on, and they look for it — because it’s a kick-off to the season.”
Mintrone is already thinking beyond Mayfest. Up next for the Better Bennington Corporation will be many more family-friendly and community-centered events for the downtown area.
“The third Thursday in June, we have another Hemmings Cruise In,” said Mintrone, adding that the event would coincide with a Thursday Night Live music event — part of a series. Then, waving her hand up the street, “That happens all here on Main Street. The road is closed, with all classic cars that line the streets, and we’ll have a band set up over here — and it’s just really, really upbeat. People of all generations come to see the cars because they span such a long period of time.”
“But – in July – on the third Thursday, we have a trifecta,” exclaimed Mintrone, with a grin. “We have Midnight Madness, the Hemmings Cruise In, and the Thursday Night Live — all on the same day.”
Held rain or shine, Bennington’s annual Mayfest event takes place on the Saturday of Memorial Day weekend.
For more information on upcoming BBC events, visit betterbennington.com/events.