Join us for a Day Filled with Tasty Fun.

The third annual Rutland Whoopie Pie Festival will be an all-day extravaganza with something for everyone! Enjoy the day with music, performances, activities, and diverse foods.

Schedule of Events

Adult and Kids Activities
Join us on the green for fun and easy activities with Come Alive Outside! Everyone's welcome!

12:00 pm - 5:00 pm: Caricature Artists
Capture the joy of the day with a twist of humor through the strokes of our caricature artists! Get your own quirky and exaggerated portrait sketched by our skilled artists. It's a fun, unique memento that encapsulates the festival's spirit. Step right up and see yourself transformed into a whimsical work of art that you can cherish long after the sweet treats are gone.

12:00 pm - 5:00 pm: Face Painting
Our skilled face-painting artists will turn your smile into a work of art. This is an excellent opportunity for kids and the young to enhance their festival experience with a touch of whimsy. So why not come along, get painted, and celebrate the joy of whoopie pies with us?

12:00 pm - 5:00 pm: Food Trucks
Don't miss the chance to savor delicious bites from the food trucks parked on Center Street and Merchants Row.

Featured Food Trucks:

Hangry Hogg (on Center Street) - website, facebook
The Rollin' Rooster (on Merchants Row) - website, facebook
There will also be Mexican food provided by Daniel Mora of Vista Senior Living and a Hot Dog cart, Grumpy Veterans Dogs run by Warriors SOAR, a non-profit aimed to assist in the healing and reintegration of wounded veterans through Support, Outreach, Assistance, and Recovery.  Warriors SOAR will also be selling Pajama Grams again this year!

Plus ice cream treats by CR Concessions and Cotton Candy by Whirlies World

12:00 pm - 5:00 pm: Ga Ga Pit
Kids go "Ga Ga" for the Ga Ga Pit hosted by the Rutland Recreation Department.

12:00 pm - 5:00 pm: Green Street Challenge, Merchants Row
The Green Street Challenge will take place at Merchants Row. The event offers various activities and shows in the grassy area along Merchants Row, all hosted by our incredible partners.

Rutland Recreation Department's Ga Ga Pit
Vermont Farmers Food Center
WIC
Outright, Vermont
Wonderfeet Kids Museum
Farm & Wilderness
Come Alive Outside
Partners for Prevention
Rutland County Parent Child Center

12:00 pm - 5:00 pm: Whoopie Pie Vendor Samples
Secure your tickets for an exclusive taste test of the delectable whoopie pie creations our extraordinary bakers have whipped up for the festival! Your palate will be the ultimate decider as you judge these sweet confections. Found a favorite? Indulge further by purchasing additional treats from each baker's booth. Get ready to savor every moment-and every bite!

Magician Act
Experience the enchantment of Tom Joyce, the Magician, at our Whoopie Pie Festival! Prepare to be captivated by his magic act, filled with a delightful blend of humor and jokes that will leave you both amazed and chuckling. Tom's interactive performance will surely be a highlight for festival-goers of all ages. Don't miss the chance to witness the wonder and share the laughter with Tom Joyce!

Red Trouser Show
Join the Red Trouser Show at the corner of Merchants Row and Center Street to enjoy a famous street performance featuring chair and ladder balancing acts, juggling, and acrobatics.

Show 1: 12:30 PM
Show 2: 2:30 PM

12 pm - 3 pm: Star Wars Characters and Ghost Busters
Meet your favorite Star Wars characters and Ghost Busters at the festival! Say hello and snap photos with the galaxy's most iconic heroes and villains.

"The Largest Whoopie Pie in Rutland"
Join us for the unveiling of Rutland's largest whoopie pie! See what it takes to put together one of the most enormous whoopie pies you will ever see in person. A big shoutout to the hardworking team at Dream Maker Bakers for tirelessly building this monster of a treat!

Whoopie Pie Awards
Keep an eye out - we'll reveal the "Best…" category winners. Get ready to see who takes the top spots!