The temperature may be dropping, but Hamilton Halton Brant’s event calendar is coming in hot all sorts of late fall fun. Here are just a few of the events that are on our radar as the race toward the holiday season begins!
Grab some Halloween Treats
Georgetown’s Masquerade on Main & Mill on October 25 transforms downtown into a Halloween destination. More than 2,000 families showed up last year for trick-or-treating at local businesses from 4pm to 6pm, followed by a new Downtown Scavenger Hunt from 6pm to 7:30pm where teams race to solve clues for prizes. The evening wraps up with an all-ages dance party on Main Street until 9pm.
On the same day over in Downtown Milton, the tiniest trick-or-treaters turn up for Tiny Tots Trick or Treat, where local businesses hand out treats during daytime hours making it perfect for young families.
The Ancaster Halloween Market at Ancaster Fairgrounds and the Spooks and Spells Market at Andrew’s Farm Market & Winery offer some spooky shopping for those who prefer browsing seasonal vendors and makers.
Tiny Tots Treat or Treat, Downtown Milton
Knock Back Some Spooky Brewskis
Music Trivia Bingo on October 31 at Flux Brewing Co. is sending you into another dimension of sound, sight and mind. This special halloween edition will test your bravery with almost familiar themes and thrilling scares! Get ready for the funk of forty thousand years and enjoy some craft beer with some grizzly ghouls.
Too spooky? Then relax with some prime Lagershed brews at Shawn & Ed Brewing Co. while listening to TRICKBAG on the 31st. Enjoy the lineup of blues, roots and R&B in their repertoire, and come dressed up to win some fun prizes as well.
Or head on a tasting tour across the region by exploring our True Brew Path for flavours, brews, wine, spirits and everything in-between!
Find the Scariest Jack-o-Lantern Trail
Royal Botanical Gardens brings back its popular Great Pumpkin Trail with tickets still available for October 26. This year features 10,000 real pumpkins arranged in artistic displays throughout Hendrie Park, plus a candlelit one-kilometre trail through Hendrie Valley, live entertainment, and food trucks.
Spooktacular at Mountsberg has been scaring all October and will be closing on October 26 so catch some family-friendly Halloween fun before it’s gone!
Pumpkins After Dark at Milton Fairgrounds continues through November 1, with this year’s new addition being a Dracula’s Castle Maze in an already fairly dark destination… Experience thousands of hand-carved, illuminated pumpkins arranged in elaborate displays and scenes, and test your bravery after dark!
Indulge in the Arts
Art Gallery of Burlington‘s REVEL25 on November 7 promises “total disco mayhem” with its 70s glam theme. Expect fierce drag performances, DJs spinning all night, bold art installations, and bites from top local chefs. This third annual art bash supports accessible arts education, consistently sells out, and is going to be even larger as they celebrate their 50th anniversary. Get more details.
Or visit AGB in the day and explore Gikinoo’amaatowin – This Is All Learning, an exhibition running through January 25, 2026 that explores methods of storytelling, healing and resistance found within Indigenous women’s artistry. The works of Anishinaabe artists Jean Marshall and Nicole Richmond remind us “that knowledge is not confined to classrooms or institutions. Learning happens while harvesting, sewing, beading, and dancing, through ancestral practices, and while being in relation with the land and each other.”
Over in Hamilton, the Art Gallery of Hamilton presents AGHFest from November 13 to 23, featuring film screenings, performances, and special programming that brings the gallery to life after hours.
The gallery’s major exhibition Metamorphoses: Visions of Antiquity in the Modern Era continues through January 4, 2026, exploring how artists reinterpret classical mythology for contemporary audiences. These groundbreaking works are displayed alongside highlights from the 1800s and 1900s, drawn from the Art Gallery of Hamilton’s collection and major public and private loans. As part of the exhibition, visitors will enjoy the rare opportunity to experience Marc Chagall’s Daphnis & Chloé—a series of 42 colour lithograph prints—in its entirety.
Step Back in Time
Museum exhibitions offer indoor exploration when November weather turns unpredictable. Oakville Museum presents two engaging exhibitions: Wicket Fun explores the history of cricket in Oakville, while Seven Glorious Virtues examines Victorian moral values through the museum’s collection.
Joseph Brant Museum’s Iron Willed: Women in STEM celebrates pioneering women who broke barriers in science, technology, engineering, and mathematics until March 29
Canadian Warplane Heritage Museum features Maple Leaves and Tulips, an exhibition celebrates the 80th anniversary of victory in Europe while exploring Canada’s role in liberating the Netherlands during WWII and the enduring friendship between the two nations.
Shop, Love & Support Local
Hamilton Day on November 1 & 2 celebrates everything local with a city-wide weekend of events, walking tours, live entertainment, and special deals at participating retailers, eateries, and service providers throughout Hamilton.
Paris Fairgrounds hosts A Holiday Market in Paris on November 8 & 9, bringing together over 100 artisans, makers, and vendors for early holiday shopping in a festive setting.
The 4th Christmas Market in the Glen is returning to Glen Williams on December 7 – while no information is out yet, we definitely have our eyes on this cozy event in a hallmark destination!
The stretch from Halloween through early December is filled with weekend reasons to bundle up and head out! Whether you’re chasing jack-o-lanterns, raising a glass at a disco-themed art bash, appreciating multi-medium art, or learning from the past, there’s something for everyone across Hamilton Halton Brant this Fall!
