Fall Vibes & Festivities in Hamilton & Ancaster
September is one of the most exciting times of the year in Hamilton and Ancaster. The heat of summer gives way to cooler evenings, the trees begin to turn brilliant shades of orange and red, and the community comes alive with fall events. From live music festivals to traditional fairs, the region is filled with activities that bring people together to celebrate culture, food, and the beauty of the season.
For locals, it’s a chance to reconnect with the community. For visitors, it’s the perfect opportunity to explore everything the area has to offer—whether you’re here for a weekend getaway, a family trip, or attending one of Ancaster’s many fall weddings.
And when the day’s festivities wind down, there’s no better place to relax than The Barracks Inn. Located in the heart of Ancaster, our boutique hotel offers the perfect blend of historic charm and modern comfort, making it an ideal base for exploring Hamilton and the surrounding areas.
Here are some of the top events happening this September that you won’t want to miss:
🎶 Supercrawl (Hamilton)
One of Hamilton’s most iconic events, Supercrawl takes over James Street North each September with live music, art installations, local food vendors, and shopping. The festival attracts thousands of visitors and showcases the city’s thriving arts and culture scene. Best of all—it’s free to attend!
This year’s lineup includes headliners like Born Ruffians, Basia Bulat, Godspeed You! Black Emperor, Steve Strongman, TOBi, and Donovan Woods, along with dozens of other artists across multiple stages.
When: September 12, 13 & 14, 2025
Where: James St. N, Downtown Hamilton
🎡 The Ancaster Fair
The Ancaster Fair is a beloved community tradition dating back over 170 years, and 2025 marks a major milestone — the 175th Ancaster Fair!
From September 18–21, 2025, the Ancaster Fairgrounds will host this exciting event filled with classic fall fair experiences. Visitors can enjoy agricultural demonstrations, livestock shows, midway rides, live entertainment, and delicious fair food.
A highlight of the weekend is the demolition derby, always a crowd favourite. In addition, a local marketplace with vendors will be open on September 19 and 20, showcasing handmade goods, crafts, and local products.
Perfect for families, couples, and anyone looking for that small-town Ontario charm, the Ancaster Fair is just minutes from The Barracks Inn—making it easy to enjoy the fun without the hassle of travel.
When: September 18–21, 2025
Where: Ancaster Fairgrounds
🍺 Hamilton Oktoberfest & Fall Beer Festivals
Hamilton loves a good fall celebration, and September often brings Oktoberfest-style events and local beer festivals. It’s the perfect time to explore the region’s thriving craft beverage scene.
Local favourites include:
- Brewer’s Blackbird Kitchen & Brewery (Ancaster) – craft beer and chef-inspired food
- Shawn & Ed Brewing Co. (Dundas) – historic brewery known for its lagers and ales
- Fairweather Brewing Co. (Hamilton) – creative, small-batch brews
- Steel Town Cider (Hamilton) – artisanal cider made from Ontario apples
- Collective Arts Brewing (Hamilton) – beer meets art in this internationally recognized brewery
Whether you’re raising a stein at a festival or visiting these breweries directly, September is the perfect time to sample local flavours and celebrate fall in Ontario.
When: Mid–late September
Where: Various venues across Hamilton
🎭 Ancaster Memorial Arts Centre – Fall Performances
The Ancaster Memorial Arts Centre offers a full schedule of performances, from live theatre and concerts to comedy nights. September is the perfect time to catch a show before or after exploring Ancaster Village.
One highlight this fall is The Vagina Monologues by Eve Ensler on September 12, 2025 — a powerful and thought-provoking performance that celebrates women’s voices and experiences.
When: Various dates in September
Where: Wilson Street East, Ancaster
🚜 Harvest Festivals & Farmers’ Markets
September marks the peak of harvest season, and Hamilton & Ancaster have fantastic farmers’ markets and fall festivals. Stroll through stalls filled with fresh produce, baked goods, and local crafts. Don’t miss the Ancaster Farmers’ Market, which runs weekly and offers a true farm-to-table experience.
When: September (weekly events)
Where: Ancaster Village Green + markets across Hamilton
🎨 Art Crawls & Cultural Events
In addition to Supercrawl, Hamilton’s monthly Art Crawl continues in September with local galleries, shops, and street vendors staying open late. It’s a great way to experience the city’s creative energy and discover one-of-a-kind finds.
When: Second Friday of September
Where: James St. N, Hamilton
Stay Close to the Action at The Barracks Inn
After a day of music, food, art, or fall fair fun, there’s no better place to unwind than The Barracks Inn. Located in the heart of Ancaster, our boutique hotel offers:
- Luxurious, spacious suites with modern amenities
- Complimentary gourmet continental breakfast
- Convenient access to Hamilton and Ancaster’s top events
- Historic charm combined with boutique comfort
Plan Your September Getaway
Whether you’re visiting for Supercrawl, the Ancaster Fair, or a weekend of fall colour tours, make your stay unforgettable at The Barracks Inn.
View Our Suites and book your stay today. Experience boutique comfort, historic charm, and modern luxury right in the heart of Ancaster.