A Harvest of music influence, community, pride

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This article was published 31/05/2025 (467 days ago), so information in it may no longer be current.

Terry O’Reilly was in his early 20s when he was faced with one of the toughest decisions he would ever have to make: pursue a comfortable career in the business world or follow his heart and try to make a living in the often tumultuous music biz.

At the time, he’d recently started a day job with a customs firm at a Toronto shipyard after graduating from business school. He was also working evenings and gaining some notoriety as a singer and guitarist with a local bar band.

Things came to a head when O’Reilly’s employer told him he needed to choose one vocation or the other. That’s when he bid adieu to the business world and took up the career in music that would endure for more than four decades.

It was decision he never once questioned, says his wife of 55 years.

“I would say he did not have one second’s regret,” says Margaret O’Reilly. “Music was his whole life. I think it was just in Terry’s blood.”

That music life began in earnest in the early 1960s when O’Reilly, who grew up in London and Guelph, started playing various gigs with his band on the Toronto bar scene. One of the early highlights was when one of his first bands opened for famed rock group The Byrds at T.O.’s Varsity Stadium in 1965.

O’Reilly moved to Winnipeg in 1968 to be closer to Margaret, who he’d been dating for some time and who had recently accepted a job in the Manitoba capital. He soon recruited several local musicians to join him as part of Coach N Four, a rock ‘n’ roll foursome that became a regular on Winnipeg’s night club scene.

A few years later he started what became arguably his most successful band, Harvest. The country group was a regular on the local music scene and gathered a strong following across Western Canada.

O’Reilly was Harvest’s rhythm guitarist and affable frontman. Even though the band maintained a hectic performing schedule, O’Reilly also managed to find time to back up performers like Buddy Knox (Party Doll) and Ronnie Prophet (Good Ol’ Boys) whenever they were in Winnipeg.

Doug MacFarlane first got to know O’Reilly in 1972 when he was helping run a booking agency here in Winnipeg. The two became friends and MacFarlane would often sit in on drums for O’Reilly’s band.

“He always had a good band. He always had good musicians with him. They were booked probably 50 weeks of the year,” MacFarlane recalls.

“And he was an excellent frontman and lead singer. He was just a great performer. He could sing pretty much anything.”

It was thanks to music that Terry and Margaret had first met back in 1967.

Terry and his band were rehearsing for a gig at a nightclub in Thunder Bay. Margaret was there waiting to give a friend a ride home. Terry came over to her table and struck up a conversation, inviting her to come back later that evening to see his band perform. They started dating a short time later and were married on April 19, 1969.

“I don’t know, I guess we just clicked,” Margaret recalls, laughing. “I was impressed with him and I guess he must have been impressed with me.”

Together they raised a family of five that included son Brent and daughters Shauna and Kari. O’Reilly’s already hectic schedule soon became even busier. In addition to continuing to perform full-time, he took on a day job working for the booking agency MacFarlane ran in 1972. They did that for a couple of years before starting their own agency, Showcase Productions.

Shauna says one of her earliest memories of her dad was how she and her siblings would serve as his unofficial roadies during rehearsals and help carry music equipment to and from his car. While his busy work schedule didn’t leave him much downtime, O’Reilly never lost sight of the importance of his family.

“He always wanted family around for Sunday dinners and that kind of thing. And every year we rented a cottage in the Lake of the Woods so we could spend time together. That sort of thing is definitely prominent in my mind,” she says.

While O’Reilly’s love of music never wavered, his days as a performer started to wind down in the 1980s when many local bars and nightclubs started to phase out live performers in favour of recorded music.

In 1989, he quit performing and left Showcase to become director of promotions for the Winnipeg Convention Centre, where he ran everything from the venue’s annual wedding show to its Oktoberfest celebrations. He was also responsible for booking many big name acts that graced the Convention Centre stage including the likes of INXS, the Black Crowes, Kenny Rogers, B.B. King and the Backstreet Boys.

Shauna says one of her most enduring memories of that was getting to go back stage and meet face-to-face with such artists as INXS frontman Michael Hutchence.

“That was really cool. My friends always thought my dad was so cool because we always got to sneak in the back door or got advantages at concerts like free drinks,” she says, laughing.

O’Reilly’s wife still has stacks of hand-written letters from many of the artists O’Reilly helped bring to Winnipeg, first with Showcase Productions and later with the Convention Centre. Many of them praise his professionalism and problem-solving abilities.

“If anybody had a problem, he wanted to fix it,” she says.

MacFarlane says while he respected his friend’s musical abilities, what he admired the most was his grace under fire. Even when others lost their temper, O’Reilly remained calm and collected.

“It was very easy to get along with Terry. I think all the time that him and I worked together, we never had a harsh word between us for each other,” he says.

“He was always very reasonable and had good common sense. And he was always kind of an up person; I am too. I think maybe that’s kind of why we got along so well together. We always joked about things and rolled with the punches, so to speak.”

The way O’Reilly treated people likely had something to do with his strongly held faith. He was raised Anglican and was a strong believer in the notion of treating others as you would like them to treat you.

Although he didn’t have many hobbies, O’Reilly was a self-described car buff and loved to have a nice, new set of wheels, according to his wife.

Following his retirement from the Convention Centre, the couple moved back to London, Ont. to be closer to Shauna, her husband Jason and their son True, who Terry adored.

O’Reilly died on Dec. 11, 2024 after suffering a stroke in June and a series of subsequent ministrokes. A memorial service was held for him Dec. 17 at The Church of St. Jude in London.

While his loss was sad news to everyone who knew him, Margaret says her husband would not have wanted a lot of tears shed on his behalf.

“Terry would like to be remembered as being the fun guy. He loved to tell jokes and make people laugh. He had this really big laugh and would always try to get others to laugh or smile.”

fpcity@freepress.mb.ca