Rutland Whoopie Pie Festival offers sweet smiles

A man with a whoopie pie hat was seen walking around Rutland’s third annual Whoopie Pie Festival.

“I get 7 whoopie pies today for my 7th birthday,” Chase Brown, a wide-eyed 7-year-old, declared with a grin smeared in chocolate. He didn’t pause for long, turning back to his double-fisted dessert strategy, clearly savoring every moment of his special day. 

Chase’s chocolate-covered smile was a perfect reflection of the day’s festivities at the Rutland Whoopie Pie Festival on Sept. 14. The downtown streets were filled with a sweet aroma as thousands of festival goers indulged in a vast array of whoopie pies, each more tempting than the last. 

When Lori Gotshall, a first-time festival goer, was asked what she came for, she looked at this reporter and replied with a smile, “the whoopie pies.” 

This year’s festival showcased 17 vendors, each offering their own unique twist on the beloved treat. Attendees had the chance to sample flavors ranging from lemon poppy seed with blackberry filling to cinnamon roll and pumpkin with maple cream cheese.  

The sheer variety had people lined up with bags full of the delicious desserts, eager to try as many different kinds as possible. 

Among the first-time vendors was Morgan Levesque of Morgan’s Whoopie Pies, who was thrilled with the warm reception.  

“It’s my first time here … The overwhelming welcomeness of all the people that are here, just coming and saying hi and complimenting all of our whoopie pies—it’s been overwhelmingly awesome,” Levesque said, stammering with excitement. 

Returning vendor Maggie’s Munchies also had a lot to celebrate. It was their second year coming to the festival.  

“It’s our main business, and it’s been very good and always busy,” Maggie’s husband explained, as taste testers swarmed around their table. 

On the other side of the street, newcomers Cookie’s Cupcakes were equally enthusiastic.  

“We heard about it online and it’s been a lot of fun. I’m having a great time,” said Jon Bates, a friend of the owners.  

After the votes were tallied, Cookies Cupcakes emerged as the star of the festival, winning both Best Overall and Most Creative awards. Their inventive flavors and perfect execution impressed the judges and delighted the crowd, making them the highlight of the day.  

And who could forget the record-breaking whoopie pie baked by Dream Makers Bakers of Killington weighing a whopping 1,187 pounds!  

As the festival wound down, Chase and the rest of the attendees left with full bellies and big smiles, already looking forward to next year’s event. The Rutland Whoopie Pie Festival once again proved that a simple treat can bring a whole community together in a celebration of sweet, shared joy. 

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