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Fall Season in Hamilton: Your Local Event Guide 

Tuesday September 2, 2025

Hamilton

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There’s no season that shows off the Hamilton area quite like the fall. The air turns crisp, the Escarpment glows with colour and local traditions bring people together in the best ways. From pumpkin picking and fairs to arts festivals and charity events, this season is packed with things to do and reasons to get outside!

This season is one of my favourites, and below are a few of my top events to enjoy fall in Hamilton!

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Supercrawl

Kick off the fall season with downtown Hamilton’s biggest street festival. From September 12th to 14th, Supercrawl will take over James Street North with live music, art installations, food trucks, markets and pop-up performances.

It’s a vibrant celebration of creativity that draws thousands to the city’s core and kicks off the fall season in style.


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Ancaster Fair

This fall event has been running for over 170 years and is a fall favourite that blends agricultural heritage with modern fun. With livestock shows, rides, live entertainment and fairground treats, it’s the celebration of the season. This event runs from September 18th to 21st at the Ancaster Fairgrounds.

Carluke Orchards in Ancaster

Located in Ancaster, Carluke Orchards is the place to go for a true taste of fall. With 13 apple varieties available, as well as pick your own pumpkins and squash, you can spend the day choosing your fall favourites.

Next, stop by the on-site bakery for pies, muffins and other fresh-baked treats. With rows of colourful trees and plenty of seasonal goodies, it’s a picture-perfect autumn outing for all ages. The best part? Carluke Orchards is open all fall long!

Rockton World’s Fair

A fall tradition dating back over 160 years, the Rockton World’s Fair is small-town charm at its best. From livestock shows and demolition derbies to midway rides, live entertainment and classic fair food, this is one event you can’t miss! Taking place over Thanksgiving weekend, visit the Rockton Fairgrounds from October 10th to 23rd to take in this one-of-a-kind fair.

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Hamilton Fall Garden & Mum Show

The Fall Garden and Mum show at Gage Park fills the greenhouse with over 100,000 homegrown blooms. Steeped in over 100 years of tradition, this show cannot be missed.

This year’s “Under the Sea” theme will transform the space into a colourful underwater world, complete with floral sea creatures and coral reefs. From October 18th to 26th, you can participate in all the family activities, visit the on-site café and flower market – it’s a fall favourite you won’t want to miss!

Woolcott Coat Drive

Woolcott Real Estate will be hosting their 11th annual coat drive on Saturday, November 8th in support of the Good Shepherd Centre. This event takes place at 493 Dundas Street East, where the team will be accepting donations of warm coats to support those less fortunate in the community.

The Woolcott team will also have hot chocolate, coffee and snacks on hand to thank the community for their donations. This fall event is the perfect way to give back to the community we call home.

Do you have questions about living in Hamilton? Our top agents in Hamilton & Burlington are happy to help you see the big picture! Reach out today with any questions you have or call 905-332-9223 to connect with our office.

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