Experience the Rutland Whoopie Pie Festival: Fall’s Sweetest Vermont Festival
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If you’ve got a sweet tooth, be sure to mark your calendar for Saturday, September 13, 2025, because downtown Rutland is about to transform into a vibrant dessert paradise, and it’s one of Vermont’s most exciting fall events.
The 4th Annual Rutland Whoopie Pie Festival is back from 12 pm to 4 pm on Center Street & Merchants Row, and it’s shaping up to be the biggest (and tastiest) year yet.
Yes, there will be more whoopie pies than anyone could possibly eat, but this downtown event also features live entertainment, food trucks, kids’ activities, and special guests.
Highlights You Won’t Want to Miss
- Whoopie Pie Samples & Voting – Taste and vote for your favorite creations from talented Vermont bakers.
- The Whoopie Pie Mile – A fun run/walk with a sweet pit stop halfway.
- Live Performances & Music – Including magic shows, street performers, square dancing, and robotics demos.
- Family Activities – Caricature artists, face painting, hula hooping, Ga Ga pit, and more.
- Special Guests – Meet Star Wars and Ghostbusters characters in costume.
This isn’t just a food festival, it’s a community celebration packed with surprises.
Also Read: Vermont in the Fall: Essential Places to Visit While Leaf Peeping
The Whoopie Pie Mile
Kick things off early with the Whoopie Pie Mile at 11 am, starting and ending at the Rutland Amtrak Station. Sponsored by Green Mountain Power, Rutland Recreation & Parks, and Come Alive Outside, this fun run includes a mid-race whoopie pie pit stop (of course!). No timing, just laughs, cheers, and prizes for the top three finishers.
Little ones can join the free Whoopie Dash before the main event begins.
Whoopie Pie Sampling
The heart of the festival is, naturally, the whoopie pie sampling. For just $1 per ticket, you’ll get to taste extravagant pies from local bakers and cast your vote for favorites. Bakers will compete for Overall Best, People’s Choice, and Most Creative awards.
Gluten-free and vegan options will be clearly labeled and available.
Sampling runs from 12 pm to 4 pm; don’t miss your chance to indulge in these scrumptious treats!
Food Trucks & Vendors
Beyond whoopie pies, you’ll find a full spread of food trucks and vendors lining Center Street and Merchants Row. Expect everything from BBQ and smash burgers to burritos, popcorn, Indian food, cotton candy, and maple-sweet treats.
And, save room for even more dessert; Kingdom Creamery of Vermont, Sundae Sisters, and Whirlies World will all be serving up ice cream and sweets.
Wash it down at one of the beverage vendors: mocktails, lemonade, milk stations, and energy drinks will all be available.
Family Fun All Day
The Rutland Whoopie Pie Festival is as much about fun as it is about food. Bring the kids for:
- Caricature Artists – Get a cartoon portrait as a keepsake.
- Face Painting – Add a little whimsy to your look.
- Ga Ga Pit & Green Street Challenge – Outdoor games and activities hosted by local partners.
- Meet & Greet Characters – Snap photos with Star Wars heroes and Ghostbusters.
Live Entertainment
Festival streets will be buzzing with live shows and performances, including:
- The Real McCoy Street Show – A world-class comic act at 12:30 & 2:30 pm.
- Magician Tom Joyce – Magic and laughs at 1:30 & 3:15 pm.
- Whoopie Pie Eating Contests – Kids (ages 6–11) and teams (12+) compete at 1:30 pm.
- Square Dancing with Cast Off 8’s – Try your steps between 2–3 pm.
- Robotics Demonstration – Rutland Robotics Club shows off its creations at 3:30 pm.
- Whoopie Pie Awards – Winners announced on the Main Stage at 3:45 pm.
Rutland Whoopie Pie Festival: Know Before You Go
- Admission: Free, but samples require tickets ($1 each).
- Sample Tickets: Buy online in advance or on-site at four ticket booths.
- Gluten-Free/Vegan Options: Yes, available and labeled.
- Parking: Free all day at LAZ Parking Garage, 102 West Street.
- Dogs: Not this time. Please leave pets at home.
Plan Your Sweet Escape
The Rutland Whoopie Pie Festival is more than just dessert; it’s an afternoon of entertainment, laughter, and community. Bring the kids, bring your friends, and come hungry. After all, where else can you taste dozens of whoopie pies, square dance in the streets, and watch robots perform all in one afternoon?
Saturday, September 13, 2025
Center Street & Merchants Row, Rutland, VT
12:00 PM – 4:00 pm
Come for the pies, stay for the fun. We’ll see you in Rutland!
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