Adult and Kids Yoga

Join us on the green for a fun and easy yoga session with Come Alive Outside! Stretch, breathe, and feel great. Everyone’s welcome!

Adult Yoga at 1:30 pm

Kids Yoga at 3:30 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.

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 plus a Dunk Tank!
• Vermont Farmers Food Center
• WIC
• Outright, Vermont
• Wonderfeet Kids Museum
• Wild Kind Toys
• Come Alive Outside
• Partners for Prevention

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!

12:00 pm – 5:00 pm

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!

To Be Determined

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

Star Wars Characters

Meet Craig Hahn and your favorite Star Wars characters at the festival! Say hello and snap photos with the galaxy’s most iconic heroes and villains.

To Be Determined

“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!

To Be Determined

Whoopie Pie Awards

Keep an eye out – we’ll reveal the “Best…” category winners. Get ready to see who takes the top spots!

To Be Determined

The streets will be back open for regular traffic at 7:30 PM. Thanks for joining us!