Join us for a day filled with delicious sweet treats and an abundance of community fun!
At the Rutland Whoopie Pie Festival, you can enter a competition with other bakers to sell and offer samples of your own whoopie pie recipe.
Please check our FAQs prior to registration if you have any questions.
How it works.
- Bakers Deposit: $100 before July 15th, 2026 | $150 after July 15th, 2026.
- Deposit required upon registering – you will receive this back plus $750 if you attend the Festival (received upon check-in).
- You will be paid $750 to set up and provide 250 (3-inch or larger) whoopie pies for sampling at your booth. Each whoopie pie should provide a minimum of four samples.
- No-shows forfeit their deposit and will not be paid.
- All attendees will present a special ticket to receive a sample.
- Festival Ticket Sales begin at 12:00 PM. Ticket Booths will be located at the corner of Merchants Row and Center Street.
- You can sell additional whoopie pies and other baked goods.
- A 10 x 10 ft. tent & space will be provided.
- You provide all items needed to set up under the tent (tables, linens, serving utensils, etc.).
- Awards are available for the Overall Best, Most Creative, and People’s Choice Award.
- Judging will be based on texture, appearance, flavor, and creativity.
- This year (2026), judges will go to each booth and rate the samples they taste.
- A QR Code will be provided for People’s Choice Award voting.
- The Rutland Whoopie Pie Festival will also have live performances, food trucks, music and day-long activities for the whole family.
- A digital schedule of events will be shared as we draw closer to the event.
PLEASE NOTE: Your space is NOT SECURED until you have submitted your deposit (bakers) or space fee (vendors), and you have received confirmation.


