Town Day 2025 was Saturday, June 7
Exhibitors:
In process! Please check back close to Town Day!
Events Schedule — Winchester Town Day 2025
Subject to change.   •   Check the Town Day booth for updates on Town Day.   •   Rain Date: Sunday, June 8th.
Start End Kids
Location
Friday, June 6th
6:30 PM 8:30 PM Friday Night Block Party — Kid's music by Matt Heaton--, pizza and gelato available! Inside the Fire Station in case of rain! (Lucia Restorante) Fire Station A
Saturday, June 7th
8:00 AM 11:00 AM Pancake Breakfast — $7 per person (Rotary Club) Hope Church/Jenks Parking Lot E
8:45 AM 10:00 AM Town Day Road Race — Registration begins at 7:30am (WFEE) 67 Shore Road
9:00 AM 11:30 AM Fishing Derby — Register at 8:30. (Preschool Social Academy) Elliot Park/Wedge Pond D
9:00 AM 3:00 PM Petting Zoo (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 Downtown Street Fair — 200 VENDORS AND EXHIBITORS! Main, Mt Vernon, Thompson St
9:00 AM 4:00 PM Winchester Fire Department Vehicle & Equipment Display Jenks Lot E
9:00 AM 4:00 PM Winchester Police Vehicle display Jenks Lot E
9:15 AM 9:45 AM Bow Sim Mark Tai Chi Arts Jenks Stage E
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 Children's Art Show K-12 (Winchester Friends of Art) Town Hall F
10:00 AM 10:45 AM TBD — Check back for performer Common Stage C
10:00 AM 11:10 AM Jazz Ensembles (3 groups) — jazz standards, swing and bebop (Winchester Community Music School) Jenks Lot Stage E
10:00 AM 1:00 PM Mystic Lake Boat Tours — Free boat tours every 45 minutes, sign up at Jenks Center booth (Winchester Boat Club) Jenks Center booth E
10:00 AM 3:00 PM Rock N Roll RC Racing (Iron Tree Service) Jenks Parking Lot E
10:30 AM 11:00 AM WHS Graduation March — Cheer the WHS Graduating class as they march Down Mt. Vernon St, and Main St. Mt. Vernon St. A
11:00 AM 11:45 AM Karen Bernard School of Dance Common Stage C
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
11:15 AM 12:00 PM Motown Band — A special tribute to the Blues Brothers (Winchester Community Music School) Jenks Lot Stage E
12:00 PM 12:45 PM Animal Adventures — Interact with our animals! Common Stage C
12:30 PM 1:00 PM Steel Drum Ensemble — New this year! Calypso and Caribbean Music (Winchester Community Music School) Jenks Lot Stage E
1:20 PM 1:50 PM Blue Grass Ensemble — New this Year Bluegrass and Americana music (Winchester Community Music School) Jenks Lot Stage E
2:00 PM 2:30 PM Stormy Monday Blues — Rhythm and Blues, early rock music (Winchester Community Music School) Jenks Lot Stage E
2:00 PM 2:45 PM Animal Adventures — Interact with our animals! Common Stage C
2:00 PM 5:00 PM Chamber of Commerce Beer Garden — Craft Beers, music, food (Winchester Chamber of Commerce) Griffin Museum Patio E
2:45 PM 3:15 PM Village Band — World Music and Light Classical (Winchester Community Music School) Jenks Lot Stage
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
7:30 PM 8:30 PM McCall School Jazz Band Common Stage C
9:15 PM 10:00 PM Annual Fireworks Display--postponed to Sunday (Winchester Savings Bank) Over Center J

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