In process! Please check back close to Town Day!
Events Schedule — Winchester Town Day 2026
Subject to change.
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Check the Town Day booth for updates on Town Day.
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Rain Date: Sunday, June 7th.
| Start | End | Kids | Events scheduled as of May 24 2026 7:55 AM |
Location
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|---|---|---|---|---|---|---|
| Friday, June 5th | ||||||
| 6:30 PM | 8:30 PM |
 |
Friday Night Block Party — Kid's music by Ben Rudnick--, pizza and gelato available! Inside the Fire Station in case of rain! (Lucia Restorante) | Fire Station | A | |
| Saturday, June 6th | ||||||
| 8:00 AM | 11:00 AM |
|
Pancake Breakfast — Annual Rotary event! $10 per ticket (Rotary Club) | Hope Church | ||
| 8:45 AM | 10:00 AM | Town Day Road Race — Registration begins at 7:30am (WFEE) | 67 Shore Road | |||
| 9:00 AM | 11:00 AM |
|
The Calm Cove at the Fishing Derby — A peaceful space for children and families who may need a quiet break from the busy excitement of Town Day. (Preschool Social Academy) | Eliot Park | D | |
| 9:00 AM | 11:30 AM |
|
Fishing Derby — Register at 8:30. (Preschool Social Academy) | Elliot Park/Wedge Pond | D | |
| 9:00 AM | 2:00 PM |
|
Petting Zoo — Animal Affair (Winchester Co-operative Bank) | Common | C | |
| 9:00 AM | 3:30 PM |
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Drawing for Fireworks Starter! — Sign Up All Day | Town Day Booth | A | |
| 9:00 AM | 4:00 PM |
|
Winchester Fire Department Vehicle & Equipment Display | Jenks Lot | E | |
| 9:00 AM | 4:00 PM | Downtown Street Fair — 200 VENDORS AND EXHIBITORS! | Main, Mt Vernon, Thompson St | |||
| 9:30 AM | 1:30 PM |
|
Historical Trolley Rides — Narrated by Winchester Historical Society (Winchester News) | Common Bus Stop | C | |
| 9:30 AM | 4:00 PM | Winchester Artists Network Art Show — Winchester Room at Town Hall | Town Hall | F | ||
| 9:30 AM | 4:00 PM |
|
Children's Art Show K-12 — Winchester Schools Art Department | Town Hall | F | |
| 10:00 AM | 12:00 PM |
|
Diaper Derby NEW for 2026! — Watch babies race! Presented by the Winton Club. Registration begins at 10:00am. First race at 11:00 | Common | C | |
| 10:00 AM | 12:00 PM |
|
Kids' Olympics on the Common — Child friendly activities (Preschool Social Academy) | Common | C | |
| 10:30 AM | 12:00 PM | Mystic Lake Boat Tours — Free boat tours every 45 minutes, sign up at Jenks Center booth (Winchester Boat Club) | Jenks Center booth | E | ||
| 11:00 AM | 1:00 PM |
|
DIY Wands — Design and build your own magic wand! Details at https://winpublib.assabetinteractive.com/calendar/diy-wands/ | Library Lawn | ||
| 12:00 PM | 1:00 PM |
|
Matt Heaton and the Outside Toys — Music for Kids and the Adults Who Love Them! (Winchester Unitarian Church) | Church-Parkway @ Main St. | J | |
| 2:00 PM | 2:00 PM |
|
Rubber Duckie Race — In the Mill Pond | Main St. | G | |
| 3:00 PM | 4:00 PM |
|
Best in Show Dog Show (Register at 2:30) — Categories: Best Costume, Car, Mutt, Non-Doodle, Trick (Small Dog), Trick (Big Dog), Best In Show (Ciao Bow Wow) | Common | C | |
| 3:00 PM | 6:00 PM | Chamber of Commerce Beer Garden — Craft Beers, music, food (Winchester Chamber of Commerce) | Griffin Museum Patio | E | ||
| 3:00 PM | 6:00 PM | Town Day WIne Garden - First Year! — Paired with the Chamber Beer Garden (Winchester Chamber of Commerce) | Griffin Museum Patio | |||
| 9:15 PM | 10:00 PM |
|
Annual Fireworks Display (Winchester Savings Bank) | Over Center | J | |
