Whoopie Pie Festival

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 Eating Contests Got a big appetite and a competitive spirit? Then put your eating skills to the test in our Whoopie Pie Eating Contests! Sign up HERE for either the Kids Contest (ages 6-11) or the Team Contest (1-3 people, ages 12+). Location: Main Stage @ the Intersection of Merchants Row & Center Street 1:30 pm* – 2:30 pm *Please report to the Main Stage by 1:15 pm to participate PRIZES Kids Contest: 1st place – $25 gift certificate – Michelle’s Sweet Creations (Castleton) 2nd & 3rd place – $10 gift certificate – Prouty’s Ice Cream Parlor 4th-10th place – $5 gift certificate – Prouty’s Ice Cream Parlor Team Contest: 1st place – $45 gift certificate – Brown’s Orchard (Castleton) 2nd place – $30 gift certificate – Wellness Cafe 3rd place – $15 gift certificate – Speakeasy 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