Fun Things Happening in Halton Region This Weekend
Get ready for an unforgettable weekend of events and happenings in Halton, where the spirit of fall comes alive with festivals, farm adventures, and family fun! Celebrate community at the Georgetown Fall Fair, brimming with midway thrills, live shows, and agricultural traditions, or step into a whimsical world at Andrews Scenic Acresduring the Fairy & Iron Renaissance Faire. Wander the orchards at Chudleigh’s Farm for classic apple picking, or let your pup make a splash at the OMHS Doggie Dip in Oakville and Milton. Music lovers won’t want to miss Kerrfest, filling Westwood Park with live performances and a special Kerrfest Kids day packed with activities. Whether you’re drawn to fairs, fantasy, fresh harvests, or furry friends, Halton is the place to celebrate the season in style.
Celebrate Kerrfest 2025
The 9th Annual Kerrfest & Kerrfest Kids 2025 returns to Westwood Park in Oakville from September 5 to 7, ushering in the autumn season with rhythm, community, and family fun. On Friday, September 5 (5:30 p.m.–10:00 p.m.), enjoy live performances by Bill Durst, Rawlins Cross, and Kim Mitchell. The celebration continues on Saturday, September 6 (12:00 p.m.–10:00 p.m.), with performances from Andrew Irving, Tianna Woods, The Spoons, The Box, The Lightfood Band, and Jim Cuddy. Then on Sunday, September 7 (11:00 a.m.–5:00 p.m.), the focus shifts to families for Kerrfest Kids—featuring a dance party, DJ sets, stage shows, face painting, Batmobile appearances, and a vibrant market atmosphere.
Shop the Milton Farmers’ Market
Kick off your Saturday with a visit to the Milton Farmers’ Market in the heart of downtown Saturday September 6th.
Set along Main Street, this lively market features 40+ vendors offering everything from farm-fresh produce and baked goods to handmade sauces, flowers, plants, and locally crafted artisan products. Each week brings new finds, friendly faces, and the chance to enjoy the best of local flavour and creativity. With free admission, free parking, and market hours from 8:00 AM to 12:00 PM, it’s a great way to enjoy Milton’s welcoming atmosphere and support small businesses.
Check out this year’s 2025 vendor list to start planning your visit!
Take Your Dog for a Splash!
Get ready for a splashing good time at Doggie Dip 2025—an adorable, tail-wagging fundraiser to support the animals at OMHS! This year’s event takes place at Rotary Park in Milton on Saturday, September 6 (11 a.m.–5 p.m.), featuring both a full-size pool with stairs and a wading pool with a ramp entry for first-time swimmers or pups easing into the water. Expect dog-friendly swimming sessions, a vibrant Barkin’ Market hosted by Toronto Dog Momsoffering trendy treats and pet accessories, and plenty of photogenic moments for you and your furry best friend—all while supporting a great cause.
Have an Apple Picking Adventure at Chudleigh’s Farm
Celebrate the season at Chudleigh’s Farm with the timeless tradition of fall apple picking. Stroll through the orchardand fill your basket with crisp, fresh apples straight from the tree, while enjoying the vibrant colours of autumn. Alongside apple picking, families can explore wagon rides, children’s play areas, friendly farm animals, and delicious baked treats that capture the taste of fall. It’s the perfect outing to embrace the harvest, make memories, and soak up the beauty of the countryside.
Explore the Georgetown Fall Fair
The Georgetown Fall Fair, hosted by the Georgetown Agricultural Society, returns September 5–7, 2025 with the theme “Making Farming Fabulous.” Located at 1 Park Avenue, Georgetown, the fair features midway rides, homecraft exhibits, agricultural demonstrations, and a beer tent, plus a Taylor Swift tribute on Friday night. Saturday and Sunday bring children’s crafts, milking demos, the Ultimutts Hollywoof Star Show, kids’ contests, blacksmith demonstrations, a demolition derby, live bands, and even pro-wrestling. With admission at $15 for adults, $10 for youth (8–17), and free for kids under 8, plus $10 onsite parking, it’s a full weekend of heritage, tradition, and entertainment.
Experience the Fairy & Iron Renaissance Faire at Andrews Scenic Acres
Step into a world of fantasy and folklore at the Fairy & Iron Renaissance Faire, returning to Andrews Scenic Acres in Milton on September 6 & 7, 2025 (10:00 a.m.–5:00 p.m.). Presented by Cool Aunt Creatives, this immersive event brings live sword fights, artisan vendors, interactive workshops, whimsical performances, and costumed charactersto life.
The fairgrounds transform into enchanting zones including the Performer’s Plaza, Renaissance Couture Corner, Enchanted Garden, Mystic Mercantile, Gathering Grounds, and Artisan Hamlet, all tied together by a Village Grocery offering magical treats. It’s an experience filled with music, dance, magical duels, and creative play—perfect for adventurers of all ages.
Celebrate Fall Weekends in Halton: Festivals, Farms & Family Fun
With so much to see and do, this weekend in Halton is the perfect chance to embrace the season and make lasting memories. From lively fairs and enchanting festivals to orchard adventures, live music, and furry friend fun, there’s something for everyone. However you spend it, Halton offers the perfect mix of tradition, entertainment, and community spirit!
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