This year’s Whoopie Pie Fest will be held on September 12th, 2026
A Day Filled With Tasty Fun!
Center Street & Merchants Row | 12-4PM
Save the date for the 5th annual Rutland Whoopie Pie Fest on Saturday September 12th 2026!
The fourth 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.
Activities
Whoopie Pie Samples & Voting • Green Street Challenge • Food Trucks • Caricature Artists • Face Painting • Magician • Hula Hopping • Square Dancing • Zoo-Theme Dancing • Street Entertainment • Live Music • Star Wars & Ghost Busters Characters
2026 Bakers
Coming Soon!
Congrats to the Winners!
Chloe Perry & Sweet Birch Bakery won the Overall Best & Most Creative awards for 2025 with their signature Whoopie Pies!
Holly Bromley & The Gettin’ Place won the People’s Choice award for 2025 with their Pumpkin + Maple Cream Cheese Whoopie Pies!
See You Next Year!
Do you make the best whoopie pie?
Prove it when you compete with bakers across the Northeast!
Bakers offer samples for tickets and sell goods to attendees. Awards are available for the Overall Best, Most Creative, and People’s Choice Award. Judging will be based on texture, appearance, flavor and creativity.
World’s Largest Whoopie Pie
Megan Wagner and her Team from Dream Maker Bakers in Killington, VT made history in 2024 with the World’s Largest Whoopie Pie, weighing in at a whopping 1,187 pounds!
Thank you to our sponsors!
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