The Real Sadie Grimm ride with the Under the Helmet 2026 Journey
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🗺️ Full Route Description Event Schedule & Route:
The Sadie Grimm Legacy Loop
Get ready to ride in the tire tracks of Canada’s first female motorcycle champion! We are gathering a group of riders to recreate Sadie Grimm’s legendary 1914 ride, exploring both her original route north and her historic return journey.
⏱️ Timeline – Tuesday, August 4, 2026:
09:45 AM: Meetup, coffee, and rider briefing.
10:30 AM SHARP: KSU (Kickstands Up) 🏍️
📍 STAGE 1: The Northbound Gathering
Start Point: Royal Canadian Legion Branch 215 (215 Maxwell King Dr, East St. Paul, MB).
The Route: We will head north along Hwy 9, riding parallel to the historic CPR railway lines that Sadie famously conquered on her 1914 Indian Big Twin.
📍 STAGE 2: The Tribute Photo Shoot
Destination: Winnipeg Beach Provincial Park.
What we’re doing: We will park directly at the Sadie Grimm Picnic Shelter to take our official group photos with the life-sized commemorative motorcycle sculpture.
📍 STAGE 3: The Historic Return via Teulon
The Route: To stay true to Sadie’s journey, we are returning via her challenging evening route. We will take Hwy 229 West over to Teulon, then turn south onto Hwy 7 South. This highway covers the exact marshlands Sadie bravely crossed when skeptics said it couldn't be done!
📍 STAGE 4: The Museum Stop
Stop: Winnipeg Police Museum (245 Smith St, Winnipeg, MB).
What to see: This is the home of an authentic 1914 Indian motorcycle, identical to the one Sadie rode to victory.
📍 STAGE 5: Drinks & Dinner Finale
End Point: Back to the Royal Canadian Legion Branch 215 (East St. Paul).
Wrap-up: We will ride back to our starting point to share some food, have a drink, and toast to an incredible day on the road together!
The Sadie Grimm Legacy Loop
Get ready to ride in the tire tracks of Canada’s first female motorcycle champion! We are gathering a group of riders to recreate Sadie Grimm’s legendary 1914 ride, exploring both her original route north and her historic return journey.
⏱️ Timeline – Tuesday, August 4, 2026:
09:45 AM: Meetup, coffee, and rider briefing.
10:30 AM SHARP: KSU (Kickstands Up) 🏍️
📍 STAGE 1: The Northbound Gathering
Start Point: Royal Canadian Legion Branch 215 (215 Maxwell King Dr, East St. Paul, MB).
The Route: We will head north along Hwy 9, riding parallel to the historic CPR railway lines that Sadie famously conquered on her 1914 Indian Big Twin.
📍 STAGE 2: The Tribute Photo Shoot
Destination: Winnipeg Beach Provincial Park.
What we’re doing: We will park directly at the Sadie Grimm Picnic Shelter to take our official group photos with the life-sized commemorative motorcycle sculpture.
📍 STAGE 3: The Historic Return via Teulon
The Route: To stay true to Sadie’s journey, we are returning via her challenging evening route. We will take Hwy 229 West over to Teulon, then turn south onto Hwy 7 South. This highway covers the exact marshlands Sadie bravely crossed when skeptics said it couldn't be done!
📍 STAGE 4: The Museum Stop
Stop: Winnipeg Police Museum (245 Smith St, Winnipeg, MB).
What to see: This is the home of an authentic 1914 Indian motorcycle, identical to the one Sadie rode to victory.
📍 STAGE 5: Drinks & Dinner Finale
End Point: Back to the Royal Canadian Legion Branch 215 (East St. Paul).
Wrap-up: We will ride back to our starting point to share some food, have a drink, and toast to an incredible day on the road together!
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Where is it happening?
215, Maxwell King Drive, Winnipeg, Manitoba, Canada
Event Location & Nearby Stays:
Know what’s Happening Next — before everyone else does.
Host or PublisherSous le Casque - Under the Helmet
