Town Day 2026 is Saturday, June 6
Exhibitors:
In process! Please check back close to Town Day!
Events Schedule — Winchester Town Day 2026
Subject to change.   •   Check the Town Day booth for updates on Town Day.   •   Rain Date: Sunday, June 7th.
Start End Kids Events scheduled as of May 24 2026 7:55 AM
Location
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 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

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townday@townday.org
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Winchester Town Day Committee
PO Box 721
Winchester, MA 01890