Rutland Whoopie Pie Fest

RUTLAND WHOOPIE PIE FEST SCHEDULE

Saturday, September 13, 2025 | Center Street & Merchants Row | 12:00 PM – 4:00 PM

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 – 4:00 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 – 4:00 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 – 4:00 pm

Square Dancing with Cast Off 8’s Square Dancing Club – website

Come join the fun and explore your square dancing skills!  Cast Off 8’s will being doing demos and then YOU can join in the fun!  Open to all ages!

Center Street, in front of Paramount Theatre

The MINT’s SOAP BOX DERBY

You’ve seen it as a sledding hill, but have you seen Center Street as a raceway yet? Come check out the fastest, most epic, most creative cars this side of Killington peak! 7 teams will compete in time trials, 4 teams will take home trophies, thousands of folks will be blown away! We will have open voting, so come on by and let us know who YOU think should take home the win!

Upper Center Street

Time TBD

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 – 4:00 pm

Ga Ga Pit

Kids go “Ga Ga” for the Ga Ga Pit hosted by the Rutland Recreation Department.
12:00 pm – 4:00 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 – 4:00 PM

Adult and Kids Activities

Join us on the green for fun and easy activities with Come Alive Outside! Everyone’s welcome!
1:30 pm – 2:00 pm – Try your hand at Hula Hooping with hooping super-star Emma Jean Hoops for adults and kids alike!
3:30 pm – 4:00 p m – Join Partners for Prevention and Miss Lorraine’s School of Dance as they lead a ZOO-THEMED DANCE workshop for toddlers to 6 years old.  Kids can learn to dance and make some masks!

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!
Times TBD

Street Entertainment by The Real McCoy

Brent McCoy is a world-class and wildly entertaining comic performer. His acclaimed show features breathtaking stunts, natural charisma, and a lightning fast wit. It’s a rocking circus and comedy experience, appropriate for all ages. This ain’t no imitation… it’s the Real McCoy.

Times TBD

Star Wars Characters & 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.

12 pm – 3 pm

Whoopie Pie Awards

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

Time TBD