Manitoba History: Sadie Grimm: First Canadian Woman Motorcycle Medalist

by Ross Metcalfe
Headingley, Manitoba

Number 84, Summer 2017

This article was published originally in Manitoba History by the Manitoba Historical Society on the above date. We make this online version available as a free, public service. As an historical document, the article may contain language and views that are no longer in common use and may be culturally sensitive in nature.

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This Manitoba story is about a remarkable young woman motorcyclist who, in 1914, did something exceptional on two wheels that no man could accomplish. And, for the record, this was two years before women achieved the right to vote.

Manitoba was a hotbed for motorcycle riding and racing in the early 1900s. So much so that the Canadian Motorcycle Racing Championships were held in Winnipeg during the First World War era. There were at least ten dealerships at that time where one could purchase a motorcycle, and approximately 1200 registered motorcycles. The Manitoba Motorcycle Club (MMC) was founded in 1911 to promote the sport of motorcycling. It is the oldest motorcycle club in Canada and is reported to be the fourth oldest in the world).

As the President of the MMC in 2014, I was honoured to represent the club’s induction into the Canadian Motorcycle Hall of Fame. During my acceptance speech, I made reference to the fact that the MMC was way ahead of its time in Canada for recognizing women. In the crowd that night in Edmonton, was Mary Johnson of Winnipeg, who is very instrumental in organizing events for Manitoba women motorcycle riders. Upon hearing the story, she became very interested in who Sadie Grimm was and what she did.

The following summer, on 5 July 2015, the Antique Motorcycle Club of Manitoba (AMCM), (which amalgamated with the MMC in 2010) organized a Sadie Grimm run out to Hunt’s Roadhouse north of Selkirk. Mary was contacted and told that if she would round up woman riders to participate in the event, the club would buy them their meal. Well, not only did she round up a large number of riders, but after lunch, they went on to re-enact the run to Winnipeg Beach, 101 years after Sadie did it on her 1914 Indian V Twin motorcycle.

Another thing Mary did for us was put out the word for people who were interested in doing further research on this mysterious rider. And this is where I would like to introduce you to Dr. Carolyn and Paul Peters, who spent the better part of last year taking what little information I had on Sadie, and tracking down long lost relatives in rural Manitoba and as far away as California. They are still on the hunt for information but here is what they have garnered thus far.

The 20 June 1914 headline in the motoring section of the Manitoba Free Press read “Lady Wins Gold Medal.” What made this achievement remarkable is that nineteen-year-old Sadie Mildred Grimm succeeded where many male motorcycle riders before her had failed.

On 5 July 2015, a group of women from the Coalition of Manitoba Motorcycle Groups celebrated the 100thanniversary of this ride. The event was sponsored by the Antique Motorcycle Club of Manitoba and retraced the route of one of the earliest documented feats of motorcycle tenacity and skill by a woman anywhere in North America. As far as we have been able to determine, Grimm’s Gold Medal is the first known motorcycling prize awarded to a woman in a competition open to men. A few years earlier, American Clara Wagner was denied the trophy for winning an endurance race between Indianapolis and Chicago due to her gender.

A 1913 Indian motorcycle, similar to the one ridden by Sadie Grimm, belonging to the author on display at the Winnipeg Police Museum.

A 1913 Indian motorcycle, similar to the one ridden by Sadie Grimm, belonging to the author on display at the Winnipeg Police Museum.
Source: Ross Metcalfe

Back in the winter of 1913–1914, the Manitoba Motorcycle Club had offered a medal to the first motorcyclist to make the trip from Winnipeg to Winnipeg Beach. While this fifty to sixty-mile challenge might seem an odd choice today, it was the perfect fit for the time.

By 1914, Winnipeg Beach had become one of the most desirable travel destinations from Winnipeg with many thousands travelling on as many as 13 trains a day on busy weekends. Dale Barbour’s history of Winnipeg Beach, which mentions Sadie Grimm, notes that during its heyday this was claimed to be the most profitable stretch of Canadian Pacific Railway (CPR) track in Canada.

The explosion of automobile and motorcycle ownership was accompanied by a growing dissatisfaction with the lack of serviceable roads and this spilled regularly onto the automotive pages of local newspapers and had become a growing political issue. So while it was the CPR that had made the Beach popular and accessible in the first place, there was a growing resentment that the lack of proper roads gave the railway a de facto monopoly.

It was reported that there were numerous unsuccessful attempts to make the trip to the Beach with some motorcyclists trying while the ground was frozen. Others tried in the spring break up but found the swamps impossible.

On Sunday morning, 14 June 1914, Sadie Grimm left Winnipeg on her 1914 7-hp Big Twin Indian motorcycle planning the attempt via Selkirk. This bike was Indian’s top-of-the-line offering other than an ill-fated limited-production electric-start model. Unknown to Sadie, at least one other motorcyclist was also making an attempt that day.The Manitoba Free Press described her ride as follows:

“For twenty-five miles she had to break gravel eight inches deep while going thirty miles an hour she took several graceful slides but picked herself up unhurt. From Selkirk to St. Louis (now Petersfield) the road was fair but from then on it was all bog and pot holes. After riding paths and mudholes alternatively, Miss Grimm decided to try the railroad track. This she found very bumpy but much preferable to the continual mudholes interspersed with stumps and roots. In the swampy section, Miss Grimm passed a number of high power cars abandoned in the mud while the owners went hunting (for) teams (of horses). After four hours of solid plugging Miss Grimm registered at the Empress (CPR Hotel) and was told she was the first one to make her way through this season. Miss Grimm, not satisfied with her achievement turned around after a few hours’ rest and rode back to the city via Teulon completing one of the most strenuous rides ever attempted by a Manitoba motorcyclist.”

Remarkably, she actually accomplished the feat twice the same day by two different routes! It turned out that a motorcyclist with a side-car had run out of gas west of the Beach and arrived several hours too late to claim the prize.

The seventh of eight children, Sadie Grimm was born in Milverton, Ontario in 1895 though the family resided in Gretna, Manitoba at the time. They later moved to St. Francois Xavier before settling at 589 Walker Street in Winnipeg.

We cannot say for sure how a teenaged Sadie acquired a brand new state-of-the-art motorcycle or the required skills. It is interesting that she was pictured in the Free Press wearing Indian apparel but it seems unlikely that she would have received factory sponsorship.

We do know that she had caught the eye of future husband James Roland “Jim” Cruikshank. Jim was a well-known amateur motorcycle racer having participated in a number of advertised competitions including a 1 July event in 1911 at the Portage Races as a teenager. By 1913, he had opened up an Indian Motorcycle repair shop on Main Street in Winnipeg across from what at that time were the newly built Yale and Northern hotels. In August 1914, Jim would participate in the most famous motorcycle meet ever held in Manitoba. The City of Winnipeg declared a holiday for the three-day Dominion of Canada Motorcycle Championships which included factory racers from the United States and several future Canadian Motorcycle Hall of Fame inductees. Jim would come second to Wild Bill Pelham in the 5-mile 7-hp sidecar event. There is no record of who was in Jim’s sidecar.

The unusual nature and challenge of women riding motorcycles in this period is underscored by the Van Buren sisters’ experience when they were arrested for wearing men’s clothing on their famous 1916 U.S. transcontinental ride. The year 1914 was a watershed for women’s rights in Manitoba including the Nellie McClung-led mock parliament at the Walker Theatre that confronted premier Roblin’s statements on the prospect of women voting. The papers of the day included numerous articles on the evolving role and accomplishments of women.

Sadie’s novel achievement made her an obvious choice as a spokesperson on the participation of women in motorcycling. Her 25 July 1914 interview in the Winnipeg Tribune pays little attention to social convention and boldly promotes motorcycling as recommended for the well-being of women:

“My trips on a motorcycle have been one long list of pleasures. In the first place, the motorcycle is a great teacher ... it teaches (one) to be more independent on herself, to know that with a twist of the wrist she can control the powerful little machine that will carry her swiftly and safely wherever she wants to go. I don’t think anyone could recommend a better doctor than nature—plenty of fresh air and exercise are the greatest health givers ... On the two-wheeler, one can take a spin into the country after working hours in the evening or early in the morning and Sundays and holidays can be spent entirely out of doors.”

Sadie and Jim were married on 9 September 1914 at her family’s home. With the outbreak of the First World War, Jim volunteered for overseas service where he would join the newly formed Royal Air Force as a mechanic. They started a family immediately after Jim returned, with their only child Dorothy being born in 1920.

The trail on Sadie’s two-wheeled adventures runs cold after the war. A great-niece has described Sadie as a pistol but had no knowledge of her motorcycling past. The Cruikshank family’s involvement in motorcycling included Jim’s older brother Charles Gordon Cruikshank who was identified as one of two officials struck—but unhurt—by a motorcycle that had left the track at the August 1914 championships. We also know that Jim later ran an electric engine repair business in Brandon.

Daughter Dorothy passed away in 1981 after moving to California with her husband Ken Taylor and two sons. It would be interesting if Sadie’s grandsons, great-grandchildren or any other members of the Grimm and Cruikshank families have possession of the Gold Medal or other pictures and anecdotes that would help colour this story.

Sadie quietly passed in 1970. But on one day late in the spring of 1914, she did something spectacular that no one had done before her. And she did it twice!

A photograph accompanying this article is a picture of Sadie and her husband, which many believe might be them making a crossing on the Headingley ferry. Many folks don’t realize that not only were horse races held where the Headingley Recreational Centre is today but also highly competitive motorcycle races. So were they crossing the river to attend a race or just out for a ride?

Sadie Grimm and husband-to-be Jim Cruikshank aboard a river ferry with their Indian twin motorcycles, no date.

Sadie Grimm and husband-to-be Jim Cruikshank aboard a river ferry with their Indian twin motorcycles, no date.
Source: Dayton Taylor

There has been an upswell of support to formally record Sadie’s accomplishment. The first Sadie Grimm historic motorcycle ride to Winnipeg Beach was held on Sunday, 11 June 2017. It also served as a fundraiser toward building a Sadie Grimm picnic shelter at the Beach. One of the interesting facts is that Carolyn and Paul have tracked down Sadie’s grandson, who lives in California and turns out to be an avid motorcyclist. He flew in and rode a brand new Indian motorcycle on the run.


I want to thank Carolyn and Paul for all the hard work they have done and are still doing to tell Sadie’s story. They are currently putting nomination papers together to have Sadie inducted into the Canadian Motorcycle Hall of Fame.

See also:

Memorable Manitobans: Sadie Mildred Grimm (1895-1970)

We thank Clara Bachmann for assistance in preparing the online version of this article.

Page revised: 14 April 2021