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Monster Energy--Monster Million Sweepstakes
Enter for a chance to win one of 10 prizes of a trip for two to Las Vegas to attend the Monster Cup motocross race on October 13 and the chance to compete for $1,000,000. There are also 100 prizes of Monster Energy Eli Tomac jerseys and helmets. Canadians enter here.
Restrictions:  21 or older--no QC
End Date: August 31, 2018posted on May 1, 2018
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Orvis--Barbour Win A Land Rover Sweepstakes
Enter for a chance to win a restored 1995 Land Rover worth $125,000. There's a secondary prize worth $1,000 as well.
Restrictions:  18 or older--no RI
End Date: June 22, 2018posted on January 7, 2018
Thanks to: FJB for telling me about this one
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Wyndham Vacation Resorts--Don't Quit Your Daydream Sweepstakes
Enter for a chance to win $100,000 or one of three prizes of $10,000 or one of five prizes of $5,000. I believe these guys sell time-share properties so you might get a phone call from them if you enter.
Restrictions:  21 or older--in Canada, it's open to Alberta, British Columbia and Ontario only
End Date: December 31, 2018posted on January 5, 2018
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Chevrolet--20th Anniversary Of Corvette Racing Sweepstakes
Enter for a chance to win a 2019 Corvette Stingray and trip for two to Daytona, Florida with tickets to the 2019 Rolex 24 race. It's worth $69,700.
Restrictions:  18 or older
End Date: October 22, 2018posted on April 7, 2018
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EAA--2018 EAA Sweepstakes
Enter for a chance to win a Piper Cub airplane worth $60,000.
End Date: July 29, 2018posted on December 9, 2017
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Smithfield Racing--Smoke Machine Sweepstakes
Enter for a chance to win a Ford Mustang and a trip for two to Miami with tickets to a car race. The prize is worth $53,000.
Restrictions:  18 or older
End Date: October 12, 2018posted on May 7, 2018
Thanks to: Ollie for telling me about this one
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Outside Magazine--Summer Buyer's Guide Gear Giveaway (Facebook)
Enter for a chance to win a Jeep Wrangler with over $10,000 in outdoor and sports gear - worth $41,790. There are 50 secondary prizes of outdoor gear worth between $80 and $2,200 each as well.
Restrictions:  18 or older
End Date: August 5, 2018posted on May 7, 2018
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PBR--Built Ford Tough One Tough Ride Sweepstakes
Enter for a chance to win a trip for two to attend the PBR World Finals in Las Vegas from November 7-11 and a Ford F-150 truck - all worth up to $50,450.
Restrictions:  21 or older
End Date: October 28, 2018posted on January 11, 2018
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Champion Windows & Home Exteriors--$50,000 Giveaway
Enter for a chance to win $50,000 worth of Champion Windows and Home Exteriors products.
Restrictions:  Age of Majority--no FL
End Date: January 31, 2019posted on March 29, 2018
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Ford--Mustang 5.0 Fever Sweepstakes
Enter for a chance to win a $45,000 Ford Mustang GT with $5,000 in performance parts.
Restrictions:  18 or older--no AK or HI
End Date: December 1, 2018posted on February 16, 2018
Thanks to: Ollie for telling me about this one
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