The Pilgrimage

Dick Armstrong, September 28, 1940 – November 16, 2009 (Gerry Hart photo)

By Track Historian Bob Gates

Five, four, three, two, one, and they’re off! On May 12, 2026, Assiniboia Downs launched season #69 and once again my universe was back in sync. It was a cool spring evening, but no one seemed to mind. In a way, it was like the horses and their entourage had never left, but in the same breath, it also felt like something near and dear to us had been withheld for far too long.

This year’s opening day saw the Downs entertain a special guest by the name of Darryn Richard Armstrong. Darryn was on a pilgrimage to honour his father’s last wishes. The young man from Edmonton is the son of former Downs jockey George Richard “Dickie” Armstrong. Dick rode at Assiniboia Downs from opening day back on June 10, 1958, until the close of the 1969 season.

Dick’s Downs riding resume included:

• June 10, 1958: First win at Assiniboia Downs occurred on opening day in the first race ever at the Downs aboard Gold Ern.

• June 11, 1958: On only the second day of the inaugural meet, Dick scored Assiniboia’s first “hat trick.”
• June 14, 1958: Dick’s name is synonymous with the track record at the Downs for a mile. On this day, he rode Big Berne in a track-record time of 1:38. This time stood until Dick broke it with Already Dia on July 25, 1964, in a time of 1:37 & 3/5. Already Dia’s record held until July 7, 1972, when it was finally bettered by Gladiator II in a time of 1:35 & 4/5.

• July 18, 1964: Dick rode five winners on the eight-race card.
• At the end of the 1964 season, he was tied with jockey Tommy Stadnyk for most career wins (246) at Assiniboia Downs.
• July 2, 1965: Armstrong broke the tie with Stadnyk and rode win # 247 aboard Khal’s Charm to become the Downs all-time leading jockey.
• June 25, 1969: He rode four winners for owner Max Freed – of special note was that Mr. Freed bred all four horses, all were trained by Carl Anderson, and all were sired by Joe Wilson.
• July 19, 1969: Dickie won the Manitoba Derby aboard Fire N Desire. It would be his only win in the classic. The following day, Neil Armstrong, aboard Lunar Module “Eagle,” won the race to be the first man on the moon, landing safely at the Sea of Tranquility. You might say that the two Armstrongs made history, worlds apart.

• In addition to his Manitoba Derby win, Dick won the Winnipeg Futurity in 1965 and 1967, the Speers Memorial in 1967 and 1968, and the Gold Cup in 1965 and 1969.
• August 18, 1969: Dick rode his last winner at the Downs aboard Speedy Wheeler. He moved east at season’s end to continue his career at the Ontario tracks.
• In late 1970, Bobby Stewart passed Dick’s 478 Downs career win total to become the Downs all-time leading rider.

Dick lost a kidney as a result of a serious on-track accident at Woodbine in 1971. Rather than risk further injury, he decided it would be wise to hang up his tack.

Armstrong returned to the Downs in 2008 for our 50th anniversary celebrations. His contributions to the festivities were summed up by Downs Chief Executive Officer, Darren Dunn:

“Dick Armstrong was such a gentleman to engage with on this special anniversary event. He was polite, gracious, and full of positivity, while at the same time so grateful to be involved with our event and give support back to Assiniboia Downs and the industry that provided him with so many opportunities in life.” 

Sadly, in 2009, his health declined and he passed away on November 16, 2009. One of Dick’s final wishes was that the silver tray, commemorating his win aboard Gold Ern in the first race ever run at Assiniboia Downs on June 10, 1958, find its way back to the Downs. Once his loyal son, Darryn, came to grips with his father’s request and knew the time was right, he made the trip back to Assiniboia Downs to present the treasured keepsake to Downs CEO, Darren Dunn. It had to be difficult to give up something that was so dear to his family.

The silver tray is inscribed as follows:

Dick Armstrong
Who Rode
Gold Ern
First Winner At
Assiniboia Downs
Winnipeg Manitoba
June 10th 1958

On opening day, May 12, 2026, 68 years after his father won the first race in the history of the Downs, Dick’s proud son presented the tray and a 1969 Manitoba Derby keepsake to Darren Dunn following the running of the third race.

The day was special for Darryn in so many ways. He had not been back to the Downs since 1969. He was six years old at the time. The same night, he toured the jocks’ room, a place he had never seen before and yet a place where his father spent the better part of 11 years. Darryn’s evening was dominated by memories of his father’s time at the Downs all those years ago. “Memories, misty watercolored memories” that from time to time rolled down his cheeks.

Darryn struggled to find the words to describe the night, but you knew what he meant and had a fairly good idea of how he felt. In the days that followed, Darryn sent a Facebook message expressing his heartfelt thanks to Downs CEO Darren Dunn and everyone else at the track who contributed to his memorable pilgrimage.

Talk about a winning combination. The Armstrong family is a perfect “Triactor.” Dickie was a gentleman and a class act, “Mrs. A,” as I like to call her, is a lovely, sweet lady, and their only child, Darryn, always felt that Assiniboia Downs was their home away from home.

On behalf of his late father and his mother, who wasn’t up for the trip back to the Downs, one very honoured son completed his pilgrimage.

“Assiniboia Downs will always be in my heart.”
– Darryn Armstrong

And almost 68 years to the day, Dick Armstrong’s commemorative tray found its way home…

To Assiniboia Downs!