Downtown Winooski

11/03/2026

The November edition of the Newsletter is available online and in mailboxes! Click here to read: https://www.winooskivt.gov/DocumentCenter/View/11992/11-November-2026 📰

Winooski School District updates: Cover - Page 6
City of Winooski updates: Pages 7 - 10
Downtown Winooski & Service Providers: Page 11

10/31/2026

👻 HAPPY HALLOWEEN! 🎃

The day is finally here and we are so excited to get spooky with you all! Join us in Rotary Park from 4-9pm today for a frightfully fun Halloween bash. If you're feeling extra spirited, come by this morning and help us get set up! We'll be loading all 1,000 pumpkins into the park with the help of volunteers — just show up in the park at 10am if you'd like to lend a hand!

Speaking of help, we are so grateful to all the sponsors who are making this event possible! A huge thank you to , , , , Community Bank, and , , MTS Entertainment, , and ! We could not have this wonderful event without their support.

10/30/2026

Help needed tomorrow to set up Jack-o-Lanterns in the park! Come to Rotary Park at 10am if you're interested! 🎃

10/28/2026

We're having a blast carving pumpkins this week at the Senior Center, and we're not slowing down tomorrow! Downtown Winooski's Carving Party is tomorrow night, Thursday October 29th from 5-7pm to push us over the finish line of carving 1,000 pumpkins!

🎉 With a delightfully spooky playlist curated by Craig Mitchell, free snacks and punch, and tons of friends, it's going to be a great time!

Bring your big ideas, stretch your carving muscles, then come find your pumpkin on Saturday in the Rotary! 🎃

10/27/2026

We take a quick break from Halloween preparations to announce that the time has come... to apply to the 2026 Winooski Holiday Pop-Up Shop!

The Pop-Up will be Thurs, December 3rd from 5-9pm at a variety of downtown Winooski businesses. Applications open now til November 8 — don't miss it!

Visit downtownwinooski.org/holiday-pop-up or follow the link in our bio 💙💛

10/26/2026

We are so thankful to Redstone for their generous support of Halloween in Winooski!

For over 25 years, Redstone has developed, brokered and managed properties that inspire pride and interaction. More than just spaces to live and work, they believe in the potential of homes, offices and commercial spaces to build stronger communities and better lives.

Redstone is proud to continue their longstanding support of this wonderful community event — this photo is from their team pumpkin carving in 2024! See you soon for Halloween in Winooski in Rotary Park on October 31st!

10/24/2026

🎃🎃🎃

Every Halloween, Rotary Park in downtown Winooski fills with jack-o’-lanterns. 1,000 jack-o’-lanterns. Here's how to see them, plus ways you can help out with this incredible event. More in the comments. 👇👇

10/23/2026

🎃 No one does Halloween like Winooski, and we're giving you a little sneak peek of what to expect 👀

🎶 DJ beats from Matt Hagen (4-6) and CRWD CTRL (6-8:30) PLUS a spooky playlist curated by Craig Mitchell to finish out the evening (8:30-9)
😈 A spooky triple drag performance by Lucy Goosey, Jizzo, Alaskan Pipeline followed by Sasha Sriracha
🍷 Drinks for sale from Specs
🍿 Hot popcorn for sale by Downtown Winooski

A sweet kids party from 4-6 featuring:
🛍️ Candy bag decorating in Rotary Park — stop here first to get a map and decorate your bag before going around the Rotary!
🍬 Downtown business trick or treating
🗺️ Pumpkin scavenger hunt
📖 Halloween StoryWalk from Winooski Memorial Library
🎯 Fun Halloween carnival games
🎨 Free face painting

Then, when night falls:
💡The display of 1,000 pumpkins lights up
📸 Photo booth (donations encouraged!)
🖌️ Halloween button making (donations encouraged!)
🧙 Tarot, palm, and astrology readings by Bear Moon Botanica, Nikki Leigh, and The Little Cat

We've got one killer celebration lined up for you and we can't wait to see you there!

10/21/2026

🔪 You are formally invited to help us carve 1,000 Jack-O-Lanterns!

🎃 Carving takes place at the Winooski Senior Center at 123 Barlow St. Tuesday through Thursday next week! Here's the full schedule:

Tuesday 10/27: 10am-4pm, 5pm-7pm
Wednesday 10/28: 10am-12pm (Carving Breakfast for Senior Citizens), 12pm-4pm, 5pm-8pm
Thursday 10/29: 10am-4pm, 5pm-7pm (Downtown Winooski Carving Party feat. tunes and refreshments)

🕓 Note that we take a break from 4-5pm each day to catch up on pumpkin prep before the evenings!

🏃 Need to take your pumpkin on the go and carve at home? Pick up a pumpkin any time during open hours, but be sure to bring it back by noon on Friday so we can get it ready to head to the park on Saturday. Please make sure you carve your gutting hole at the BOTTOM of the pumpkin (leave the top/stem side in-tact!) This is necessary for our pumpkin lighting system!

✨ Let's light up Rotary Park together this Halloween!

10/17/2026

Halloween in Winooski is truly a community event and it wouldn't happen without YOU! Want to help us out? Here are 3 ways to make sure this event comes back to life like a zombie every Halloween! 🧟

🎃 Adopt a Pumpkin! 1,000 pumpkins and all the fun that goes with them comes with a big price tag, and donating to the Adopt a Pumpkin campaign makes a HUGE difference! Donate at cutt.ly/adoptapumpkin
🔪 Carve! As much fun as it would be, we certainly couldn't carve hundreds of pumpkins without your help! Stop by the Senior Center during open hours to carve a pumpkin (or 2... or 3...) Visit downtownwinooski.org/halloween for all the info
🤝 Volunteer! Between preparing the pumpkins for carvers, running activities during the event, and helping folks get into the park safely, there is a lot to be done! Sign up to volunteer at cutt.ly/halloweenvolunteer

See you at Halloween in Winooski on Saturday, October 31 from 4-9pm! 👻