Whoopie for Local Festivals

This past weekend, The Chamber & Economic Development of the Rutland Region hosted the Second Annual Whoopie Pie Festival! The event attracted around 5,000 people to Rutland’s historic downtown to eat whoopie pies, play on a green street, watch Dream Maker Bakers create Vermont’s largest whoopie pie, and have fun!

What is a whoopie pie?

This is a common question for people who are not from New England. A whoopie pie is a delicious dessert sandwich made of two tiny cakes with a cream filling. A traditional whoopie pie has two chocolate cakes and a marshmallow cream filling.

A Baker’s Dozen (minus one)

Twelve vendors from across the east gathered to serve whoopie pie samples to eager festival attendees. Throughout the event, the public voted for the People’s Choice Award. Bakers came ready to compete. There were some traditional black and white whoopie pies, but others brought pies with vanilla cakes with an elderberry filling, maple frosting, banana cakes with peanut butter filling (called The Elvis), and some added bacon or more chocolate! The winner of the People’s Choice Award was a pumpkin spice cake with maple cream. A repeat winner from last year, The Gettin’ Place in Whitehall, New York.

A 770-pound Whoopie Pie

Dream Maker Bakers, a bakery in Killington, Vermont, returned to this year’s festival to create Vermont’s largest whoopie pie. The final product weighed in at 770 pounds, blowing last year’s 554 pounds out of the water! The bakery team had the cakes and over 400 pounds of filling delivered to the festival in a food delivery truck by Black River Produce. At the event, the team skillfully covered the bottom layer of the whoopie pie with cream and then carefully put the top layer on the entire pie. After weighing the enormous cake, it was cut up and given to people in the crowd. Other parts were portioned out and delivered to food shelves and other community organizations for further distribution. There was zero waste!

Green Street Challenge

Come Alive Outside hosted a Green Street Challenge during the event! Carpenter & Costin donated sod to lay down on one of our downtown streets, Merchants Row. This creates a grassy area in the middle of a city for kids to play! Kind of like a pop-up park! It wasn’t only for kids, two yoga classes took place during the day, one for kids and one for adults. At the end of the day, some of the sod was repurposed at local fields in need of a little help.

A Pleased Panel

Aside from the People’s Choice Award, we also had a panel of judges determine the Most Creative Whoopie Pie and the Overall Best. Our judges arrived with a big appetite and tasted one whoopie pie from every baker. The judges scored most whoopie pies highly, creating a tight margin for winning. In the end, they determined inspired cookies’ vegan chocolate whoopie pie filled with an Oreo buttercream frosting, and topped with Oreo crumbles was worthy of both awards!

Festival Fun

Sugar wasn’t the only thing consumed. There were two food trucks, The Rollin’ Rooster and Hangry Hogg, and many local restaurants were open. When not playing on the green street or eating, there were caricature artists, face painters, a photo booth, a bike rodeo where kids learn how to ride bikes on a road, and stations with information and fun activities!

If it were not for our community partners and premiere sponsor, Heritage Family Credit Union, the festival would not have been as successful. Rutland County has a talent for coming together and helping create wonderful events like this! If you are interested in learning more about this beautiful place so many have made their home, connect with us here! We are always happy to discuss opportunities in our region.