Experience the Rutland Whoopie Pie Festival: Fall’s Sweetest Vermont Festival
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If you’ve got a sweet tooth that just won’t quit, clear your calendar for Saturday, September 12, 2026, because downtown Rutland is about to turn into a full-blown dessert paradise, and it’s one of Vermont’s most delicious fall events.
The 5th Annual Rutland Whoopie Pie Festival is back from 12 pm to 4 pm on Center Street & Merchants Row, and after last year’s crowd of roughly 8,000, this one is shaping up to be the biggest (and tastiest) year yet.
To put that growth in perspective: the festival drew about 2,500 people at its 2022 debut. Four years later, it’s welcoming bakers from all over New England and pulling in triple the numbers. Not bad for a festival celebrating a cream-filled sandwich!
Yes, there will be more whoopie pies than any reasonable person could eat (I speak from experience). But this downtown celebration also features live entertainment, food trucks, kids’ activities, and special guests.
New this year, downtown merchants are keeping their doors open during the festival, so you can duck into the local shops and restaurants between samples.
Highlights You Won’t Want to Miss
- Whoopie Pie Samples & Voting: Taste and vote for your favorite creations from talented bakers across Vermont, New Hampshire, Maine, and Massachusetts.
- The Whoopie Pie Mile: A fun run/walk with sweet pit stops along the way, at a brand-new location this year.
- Live Performances & Music: Comedy, stunts, magic, street performers, square dancing, and more.
- Family Activities: Caricature artists, face painting, hula hooping, and zoo-themed dancing.
- Special Guests: Meet Star Wars and Ghostbusters characters in costume.
Also Read: Vermont in the Fall: Essential Places to Visit While Leaf Peeping
The Whoopie Pie Mile (New Digs This Year)
Kick things off early with the Whoopie Pie Mile at 10 am.
Heads up: the Mile has a new home for 2026, starting and ending at the Rutland Community Center Field, 134 Community Drive. It’s a family-friendly one-mile run/walk with four sampling stations along the route, because who says you can’t have a little snack mid-race?
Registration is $10 for adults and youth ages 12 and up, and free for kids 11 and under. Each participant gets four free tasting tickets for the festival itself, so the Mile pays for a good chunk of your sampling. Little ones can join the free kids’ dash for ages 8 and under.
Whoopie Pie Sampling
The heart of the festival is, naturally, the whoopie pie sampling. For just $1 per ticket, you’ll taste extravagant pies from local and regional bakers and cast your vote for your favorites. Bakers compete for top honors, and past winners have included Chloe Perry of Sweet Birch Bakery and Holly Bromley of The Gettin’ Place.
Gluten-free and vegan options are clearly labeled at the booths, complete with QR codes so you can vote on the spot.
Sampling runs from 12 pm to 4 pm, so pace yourself and don’t miss your chance to indulge.
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 barbecue and burgers to ice cream, cotton candy, and plenty of maple-sweet treats. Come hungry, leave rolling.
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 – Take home a cartoon portrait as a keepsake.
- Face Painting – Add a little whimsy to your look.
- Hula Hooping & Zoo-Theme Dancing – Games and activities to keep everyone moving.
- Meet & Greet Characters – Snap photos with Star Wars heroes and Ghostbusters.
Live Entertainment
Festival streets will be buzzing with live shows all afternoon. This year’s lineup includes:
- The Real McCoy Show – Greensboro’s own Brent McCoy returns with his crowd-pleasing mix of comedy and stunts.
- Magic, Music & Street Performers – Roaming entertainment to catch between samples.
- Square Dancing – Try your steps in the middle of the street.
- Whoopie Pie Eating Contests – Watch the brave few take on more pie than seems wise.
- Whoopie Pie Awards – Winners announced on the Main Stage before the day wraps.
The organizers post the full schedule with performance times as the festival gets closer, so check the official site before you go.
A Whoopie Pie for the Record Books
Bragging rights: back in 2024, the festival built the World’s Largest Whoopie Pie, tipping the scales at a staggering 1,187 pounds. No word yet on whether they’ll try to top it, but it’s proof this town does not do dessert halfway.
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 the Center Street booths. Cash, card, and Apple Pay accepted.
- Gluten-Free/Vegan Options: Yes, available and labeled.
- Parking: Free all day at the LAZ Parking Garage, 102 West Street.
- Dogs: Not this time. With crowds this size and this many kids around, it’s best to leave your pup at home for the day.
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 shop downtown all in one afternoon?
Come for the pies, stay for the fun. We’ll see you in Rutland!
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