2024 WHOOPIE PIE BAKERS 

GF – Gluten Free

V – Vegan

Busy Bee Bakery, Wallingford, VT  

Cookie’s Cupcakes, Otis, MA instagram / facebook

Custom Cakes, Brookline, VT facebook

Dream Maker Bakers, Killington, VT website

Erika Grosso, Home Baker, Rutland, VT, vegan options

KJ’s Kitchen, Derby, VT  facebook

Maggie’s Munchies, Nashua NH website, GF, Dairy, Soy free options

Mitchell’s Delights, Charlestown, NH  Sweet, Savory, Organic

Queen B’s Bakery, Livermore, ME   website / facebook

Sweet Birch Coffee Roasters & Bakery, Wallingford, VT  website / facebook

Sweet Sunrise, Saco, ME facebook

The Culinary Students at Marble Valley Correctional Center, Rutland VT

The Gettin’ Place, Whitehall, NY – Winner of People’s Choice Award 2 yrs running!

The Sanctuary, Rutland, VT  website, facebook

Time Out for Whoopie, Essex, VT website

Vermont Gluten Free Bakery, Montpelier, VT website

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

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

Listen to the sounds of steel as The Panhandlers perform a Concert! 

This 12-person steel band has been playing for over 20 years and they play a mix of Caribbean tunes, pop songs and jazz standards!

Center Street, in front of Paramount Theatre

12:00 pm – 1:30 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

2:15 pm – 3:30 pm

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

1:00 pm – 2:30 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

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!

1:30 pm – 2:15 pm

3:30 pm – 4:30 pm

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 & 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

“Going for the record with the LARGEST WHOOPIE PIE IN THE WORLD!”

Join us for the unveiling of THE 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!

4:15 pm

Whoopie Pie Awards

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

4:00 pm

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