Field Notes: Fall Fairs and Autumn Adventures

Best in show – 175 years of the Erin Fall Fair

Since 1850 the Erin Fall Fair has been a cherished community celebration of farming and country life. This year the Erin Agricultural Society celebrates its 175th anniversary with a weekend of agricultural exhibits, parades, local food, animal exhibits and live music from October 10 to 13 at the Agricultural Society Fairgrounds. 

Fall fairs were traditionally held to showcase innovation, share new ideas related to rural living and build an appreciation for the importance of agriculture. Some of the quintessential events included horse and pony shows, tractor pulls and displays of vintage tractors, livestock shows and presentations of traditional sewing and quilting. 

Over the years the entertainment has expanded to include interactive activities for kids and a midway. New events this year include the Power Wheels Demolition Derby and a 175th Heritage Tent.

Prodigious performers 

Get ready to be wowed at this year’s Caledon Chamber Concerts, starting with the multi-instrumental Rebekah and Jurecka Duo on September 27 – they sing and play violins, viola, guitar, banjo uke, mandolin, harp, piano, clarinet, Hardanger fiddle, saxophone, bandoneon and accordion. Then on October 18 witness the exquisite touch of Montreal’s award-winning concert pianist Jarred Dunn. Both concerts take place at St. James Anglican Church in Caledon East.

Take a hike on Bruce Trail Day  

Explore Canada’s oldest and longest marked footpath on Bruce Trail Day with two free local club events on October 5. The Caledon Hills Bruce Trail Club will be at the Riverside Woods Nature Reserve in Mono for guided hikes, family nature hunts and a bird of prey show. At the Dufferin Hi-Land Bruce Trail Club Music Walk, local performers play in the serene forests of the Split Rock Narrows Nature Reserve in Mono.

More farmyard fun 

Put on your boots, get your passport map and head out for the Dufferin Farm Tour on September 27. It’s a self-guided tour of local farms, where you can meet the hardworking farmers and get up close with cows, goats and sheep. This annual event is a fundraiser for local food banks, and admission is a small non-perishable food donation.

A marathon of sport 

The 2025 Motionball Marathon of Sport Caledon welcomes athletes of all abilities to join a full day of fun and inclusive sports to raise funds for the Special Olympics Canada Foundation on September 13 at the Caledon East Community Complex. Each team of 10 will be joined by a Special Olympics athlete from the community.

For good causes 

The Headwaters Health Care Foundation recently announced its Smart Headwaters campaign raised $18 million for technology — including the region’s first MRI machine and an advanced CT scanner. Nearly every wheelchair, surgical instrument, monitor and diagnostic imaging machine at the Headwaters Health Care Centre is purchased through donations. Supporters can continue to help the foundation meet its goals at the Under the Big Top fundraiser on September 12 at Hockley Valley Resort. Then on October 9 the Headwaters Hike to Fight Cancer returns to the Caledon Ski Club to raise funds for cancer care at the hospital.

The Rotary Club of Shelburne’s Nutcracker Gala at the Shelburne Golf and Country Club raises funds on November 15 for the Shelburne Food Bank.

The annual Home for the Holidays Gala has supported Caledon Community Services for over 30 years. Held November 28 at the Royal Ambassador in Caledon East, this fundraiser supports local seniors, caregivers, food programs and medical transportation.

Dream jobs await

The annual Dream Career event returns October 15 at the OAS Event Centre, where more than 1,200 students Grades 8 to 12 learn about in-demand industries and employment opportunities in skilled trades. Hosted by the Dufferin Board of Trade and the Career Education Council, this event aims to connect youth with local employers — and local businesses can take part as exhibitors or sponsors.

Turning back time at the Duffy Homestead

Grit and determination must run in the Duffy family because what else could drive someone to take a perfectly good house and painstakingly restore it to its original 1800s style, brick by brick, plank by plank and beam by beam? 

Alan Duffy is a seventh-generation Duffy and the owner of the Duffy Homestead and Museum, now open for walk-ins on Wednesdays and Saturdays as well as for private tours. Alan is the descendent of Elizabeth Duffy, who emigrated from Ireland to Canada with her four children and put a down payment on 100 acres in August 1832. The property was sold in 1955, but Alan had a dream to reclaim it and restore it to a “living history museum.”

By 2019 he had managed to repurchase 60 acres and work began. On the exterior, when an attempt at removing the white paint from the red brick walls didn’t work, each brick was pulled out, turned around, and put back in place. Inside the house, behind planks of wood and layers of paint, were newspapers dating back to 1890. Hidden in the attic was a metal box holding a list of treasures, dated May 10, 1904, belonging to a 12-year-old Vera Duffy. And at the bottom of a water cistern, they discovered hand-carved children’s wooden alphabet and number blocks, circa the early 1900s. 

Today the museum offers a recreation of a typical settler home with period relics such as an antique clothes-washing plunger, wood-burning stoves, horseshoes and hoof files, and classic clothing. A First Nations exhibit displays artifacts including arrowheads, bow and quiver, and a beaver pelt from various groups that inhabited southern Ontario. There is also a permanent display room of military memorabilia from the Duffy family’s enlistments, as four of Eliza’s grandsons served in the military in the 1860s.

A free halloween film 

Grab a seat at Shelburne’s Grace Tipling Hall October 25 at 2 p.m. for a free Halloween screening of Beetlejuice presented by the Town of Shelburne and the Shelburne Arts, Culture & Heritage Committee. It is first-come, first-served, so arrive early.

Now playing 

Theatre Orangeville’s 32nd season kicks off this fall under the leadership of new artistic director Jennifer Stewart, who directs a real-life couple in The Wonder of It All, on stage from October 9 to 26, with an homage to matrimony and all its ups and downs. Then from November 27 to December 21, enjoy the “hair-larious” pantomime Rapunzel: A Braid New World, a delightful, family-friendly romp through a beloved classic fairy tale where audience participation is not only expected, but encouraged.

Canada’s most famous astronaut and prolific author, Chris Hadfield, returns to Fall Authors on Stage on October 26 to talk about his new book, Final Orbit, a Cold War thriller set against the backdrop of the 1970s space race. The talk is at the Orangeville Town Hall Opera House in partnership with BookLore. 

Singin’ in the Rain Jr, based on the iconic movie musical, takes to the stage at Grace Tipling Hall in Shelburne. Young performers belt out the show’s Hollywood standards from November 21 to 30. 

To call The Rose Brampton’s fall lineup wildly varied would be an understatement. Scott Thompson resurrects his Buddy Cole comedic persona October 2. Classic Albums Live brings the world’s best-selling album, Michael Jackson’s Thriller, alive on October 23. Rage Against the Machine guitarist and political activist Tom Morello shares A Night of Stories & Music October 30. And Jann Arden’s Christmas Tour brings the sassy Canadian singer to the stage on November 19.

Celebrate a historic hamlet 

Belfountain’s Bicentennial Bash is shaping up to be the biggest event the hamlet has ever hosted. To mark its 200th year on October 4, the Belfountain Heritage Society has planned a full day of festivities including music, a scavenger hunt, an art show with the unveiling of a bronze sculpture, a vendor’s market and vintage cars.

There will also be an appearance by the Erin Air Cadets, performances by the Sandhill Pipes & Drums Band, the 2nd York Militia – and a reenactment of the War of 1812. Don’t miss this once-in-a-lifetime event in the historic hamlet.