BIA Events
City of Woodstock's Fall Fest
Saturday, Oct. 3 from 12 – 4 p.m. in Museum Square.
Fall into fun at Fall Fest! Join us for a vibrant day of family-friendly autumn and Halloween-themed activities, entertainment, treats and more.
Main Stage Schedule
Enjoy interactive performances throughout the afternoon. Staff are currently planning the 2026 celebration, check back for updates.
Family Activities
Enjoy free fall fun from 12 – 4 p.m. Staff are currently planning the 2026 celebration, check back for updates.
HOWL-O-Ween Dog Parade
Join us at Museum Square at 2:30 p.m. for a fun-filled dog costume parade. Dress your pup in their spookiest, silliest, or most creative outfit. Prizes will be awarded for Best Costume and Fan Favourite.
Trunk or Treat
Join us from 12 – 2 p.m. (or as supplies last) for a spooktacular twist on a Halloween tradition. A Trunk or Treat is a fun alternative to trick-or-treating. Kids dress up in their favourite costumes and stroll from car to car collecting candy from creatively decorated trunks. Also, receive a City of Woodstock reusable tote to collect your treats. Registration is not required.
Autumn Artisans
Enjoy festive goodies from onsite booths.
3V3 From Downtown Basketball Tournament
The StreetFest 3V3 From Downtown Basketball Tournament
is bringing outdoor basketball to Downtown Woodstock on at Fall Fest on October 3rd!
Outdoor courts and nets will transform the downtown into a basketball showcase featuring competitive play, youth involvement, community participation, and interactive events.
As part of Woodstock’s 125th anniversary and the Downtown Woodstock BIA’s 50th year, the tournament is being organized by Why Not Us in partnership with the Downtown Woodstock BIA, and is intended to celebrate basketball culture in Woodstock while creating an exciting downtown atmosphere for players, spectators, families, and visitors alike.
Whether you’re competing or spectating, the tournament is designed to showcase the energy, camaraderie and passion surrounding basketball in Woodstock.
There’s plenty happening in Downtown Woodstock this Thursday! Spend the afternoon and evening downtown with live music, local art, late-night shopping, food and an outdoor movie in Museum Square.
Make a day of it and experience everything happening downtown.
MUSIC IN THE SQUARE – A DOUBLE TAKE
12:00 PM – 2:00 PM
2:30 PM – 4:30 PM
Enjoy live music in the heart of Downtown Woodstock with two performances throughout the afternoon. Grab some lunch, find a seat in Museum Square and enjoy some live entertainment while you’re downtown.
Art on DUB Artist Walk
5:00 PM
Join us as we officially celebrate Art on DUB, Downtown Woodstock’s newest public art initiative.
We’ll take a mini walking tour through downtown to visit the newly transformed utility boxes and celebrate the local artists whose work is now bringing even more colour, creativity and character to our streets.
The walk will feature work by:
Anne Bedard
Julie Hawkins
Laura Kay Keeling
Lindsay Liboiron
Roxanne Tochor
Come meet some of the artists, see the installations up close and celebrate the addition of new public art throughout our downtown.
Late Night Shopping
Stick around after the Artist Walk and explore downtown!
Participating businesses will be staying open later, giving you some extra time to shop, eat, explore and support local before the movie begins.
Watch for specials, features and other surprises from downtown businesses throughout the evening.
Movie in Museum Square: The Sandlot
Evening / After Sunset
Museum Square
FREE
Finish the night with a Downtown Woodstock summer favourite, a free outdoor movie in Museum Square!
We’ll be screening the family classic The Sandlot.
Bring a chair, get comfortable and enjoy the movie under the stars.
While You’re Downtown…
Several downtown businesses are joining the fun:
Fair/Square + Hidden Gem Book Co. will be open until the movie begins with a sidewalk sale featuring Blind Date with a Book, snacks and cold drinks. They’ll also be handing out 10% off coupons to moviegoers.
Tempo Restaurant is a great stop for dinner before the movie, with kids eating FREE with the purchase of an adult entrée; one free kids meal per adult entrée for children dining with you. Tempo will also be serving beverages during the movie.
Reel Treats will be onsite with popcorn and treats.
Cheesy Cow Co. will also be onsite serving gelato and sorbet.
Laros Creative Design will be there showcasing all of her custom creativity and public favourites.
Make a Day of It Downtown
12:00–2:00 PM — Music in the Square
2:30–4:30 PM — Music in the Square
5:00 PM — Art on DUB Artist Walk
Evening — Late Night Shopping
Dinner, treats & downtown specials
After sunset — The Sandlot in Museum Square
Come for one event or stay for the whole day.
Shop local. Enjoy some music. Discover new public art. Grab dinner. Then pull up a chair and finish your Thursday with a movie under the stars.
Other Events in Downtown Woodstock
Victoria Day Parade
Celebrate the Victoria Day weekend by spending some time downtown. From local shops and services to great food and friendly faces, downtown Woodstock is a great place to enjoy the long weekend.
2026 Date: Monday, May 18
WAG 60th Anniversary
Join the Woodstock Art Gallery as they celebrate their 60th Anniversary with a big party Museum Square! With fun for the whole family, enjoy live music and entertainment, shop products from local business and artists, and stop by the Gallery for tours of their new exhibits and Permanent Collection Anniversary Show.
2026 Date: Saturday, May 30
Oxford Pride Family Day
Organized by Oxford County Pride, this family-friendly event takes place in Museum Square. Expect vendors, music and a celebration of all things 2SLGBTQI+.
2026 Date: Saturday, June 13.
Please check Oxford County Pride’s website or Facebook page for event updates.
Fall Fest
Celebrate the season with us at Fall Fest in Downtown Woodstock. This annual event brings together local businesses, visitors, and the community for a day of fall-themed experiences, shopping, treats, and activities that highlight the energy and charm of Woodstock in the downtown core.
Lighting of Museum Square
Organized by the City of Woodstock, the Lighting of Museum Square is the official start of the Christmas season. Think sparkling lights, hot chocolate, music, entertainment and a very special guest all the way from the Northpole.
2026 Date: Friday, November 20.
Please check the City of Woodstock’s website for all the event details.
Santa Claus Parade
Organized by the City of Woodstock, the Santa Claus Parade features holiday-themed floats, marching bands, community groups and, of course, Santa! Departing from the Woodstock Fairgrounds, the parade will make its way along Dundas Street turning right onto Light Street to end in Victoria Park, 413 Buller St.
2025 Date: Saturday, November 15.
Please check the City of Woodstock’s website for all the event details.
