RUTLAND WHOOPIE PIE FEST SCHEDULE

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

Whoopie Pie Mile

Sponsored by: Green Mountain Power | Rutland Recreation & Parks Dept. | Come Alive Outside
Lace up for the tastiest mile in town! The Whoopie Pie Mile is a fun run/walk with a sweet stop halfway for – you guessed it – a whoopie pie! No timing, just good vibes and cheers for everyone, with prizes for 1st, 2nd, and 3rd to cross the line. Plus: a free Whoopie Dash for the littles to kick off the fun!
Click HERE to sign up
Starting/Ending Location: Rutland Amtrak Station
11:00 am

Whoopie Pie Sampling

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

Food Trucks & Vendors

Don’t miss the chance to savor delicious bites from our featured Food Vendors!

CENTER STREET
Hangry Hogg – Slow-cooked BBQ – Website | Facebook
Townline Grill – Smash burgers – Order Online | Facebook

MERCHANTS ROW
NORTH
Green Mountain Kettle Corn – Popcorn – Website | Facebook
Grumpy Veterans Dogs – Hot Dog cart – Website | Facebook
Los Morita Trio Treats – Mexican food truck – Instagram | Facebook
Bueno Burrito – Mexican food stand – Website | Facebook
Kingdom Creamery of Vermont – Ice Cream & Floats – Website | Facebook Pelletier’s Maple – Breakfast/Lunch/Dinner Truck – Website | Facebook

SOUTH
The Sundae Sisters – Ice Cream Cart – Website | Facebook
Whirlies World – Cotton Candy – Website | Facebook
Zaika – Indian food stand
12:00 pm – 4:00 pm

Beverage Vendors

Milk Stations on Center Street manned by local business Kinney Pike, a ONE Digital Co. & non-profit Rutland County Restorative Justice Center

NORTH MERCHANTS ROW
Fairly Buzzed – Mocktails – Website | Instagram

SOUTH MERCHANTS ROW
Sour Bros Lemon – Lemonade – Facebook
REZ Me Energy – Energy drinks – Website | Facebook
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

Green Street Challenge, Merchants Row

Join us on the green for fun and easy activities with Come Alive Outside! Everyone’s welcome! The Green Street Challenge will take place at Merchants Row. The event offers various activities and shows in the grassy area, 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

Ga Ga Pit

Kids go “Ga Ga” for the Ga Ga Pit hosted by the Rutland Recreation Department.
12:00 pm – 4:00 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.
12:00 pm – 3:00 pm

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.
Location: Intersection of Merchants Row & Center Street
12:30 pm & 2:30 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!
Location: Intersection of Merchants Row & Center Street
1:30 pm & 3:15 pm

Whoopie Pie Judging

It all comes down to this! Participating Bakers can have their Whoopie Pie evaluated by our esteemed panel of Judges. Bakers will be competing for the titles of Overall Best, People’s Choice, and Most Creative.
Location: Streetside Conference Room, The HUB CoWorks, Merchant’s Row
1:30 pm – 2:30 pm

Square Dancing with Cast Off 8’s Square Dancing Club

Come join the fun and explore your square-dancing skills!  Cast Off 8’s will be doing demos and then YOU can join in the fun!  Open to all ages!
Location: Center Street, in front of Paramount Theatre
2:00 pm – 3:00 pm

Rutland Area Robotics Demonstration

The incredible creations of Rutland’s Robotics club will be on full display for the entire day! Catch their demonstration right before we announce this year’s winning Bakers.
Location: In Front of the Main Stage @ the Intersection of Merchants Row & Center Street
3:30 pm – 3:45 pm

Whoopie Pie Awards

Keep an eye out – we’ll reveal the “Best…” category winners. Get ready to see who takes the top spots!
Location: Main Stage @ the Intersection of Merchants Row & Center Street
3:45 pm