Enter the Self October 2011 Specialized/Dempsey Challenge Contest for your chance to take a ride with Patrick Dempsey! You have until October 17th for your opportunity to write in 150 to 250 words why participating in the Patrick Dempsey Challenge would be meaningful to you. The prize is a custom fit Specialized 2012 Vita Elite bike valued at $810, one BA Specialized bike fit at a local Specialized Bicycle Components Dealer, airfare for yourself to Portland, Maine, a hotel room for two nights, participation in the Patrick Dempsey Challenge Luncheon, and participation in the VIP bike ride and Charity bike ride. So, if you would like to ride with Mr. Dempsey, put your thoughts to paper and, perhaps, if you are the lucky winner, you will win the grand prize!

If animals are your thing and you like stories with happy endings, then you should enter for a chance to win a trip for four to Clearwater, FL to meet Winter, the Star of the movie Dolphin Tale! One Grand Prize winner will receive round trip airfare, four nights at the Sandpearl Resort in Clearwater Beach, Florida, 4 VIP tickets to the Clearwater Marine Aquarium including a “meet and greet” with Winter, the dolphin star, and a $200 rental car gift card. Enter by October 3rd for your chance to win! May your entry be the one that splashes its way to the top! Good luck!

Enter the Chevrolet Ultimate Hunting Adventure Sweepstakes for your chance to win a Grand Prize that is kind of like wining the mega jackpot of prizes! The $69,170 Grand Prize is comprised of three components. The first part of this deluxe prize is a 2012 Chevrolet Silverado 1500 truck! Next, choose three friends to take on the Ultimate Hunting Adventure trip. You will get to choose from three trip options. Finally, you will get a $1,000 Cabela’s gift card to spend on hunting gear for your trip! The Second Prize winner will receive a 2012 Bad Boy Buggies vehicle valued at $14,199! Enter by November 30th for your chance to win!

Enter the Kate Spade/Jetsetter Sweepstakes by October 29th for your chance to win a trip for two to Milan, Italy! This trip includes round trip airfare, five nights at the luxurious Grand Hotel Tremezzo, a Kate Spade Cobble Hill travel handbag, and an American Express gift card valued at $500! This prize package is valued at $14,100! Enter today for your chance to live the good life in Italy for five nights and six days!

Oh, it’s beginning to smell a lot like the holidays! Bath & Body Works is giving away a $500 shopping spree for simply signing up for their holiday email alerts. Sign up by October 2nd so your name will be in for the drawing and you could snap up a $500 gift card! Good luck!

Enter the Sella & Mosca Jewel of the Mediterranean Sweepstakes for your chance to take a six day vacation for two to Sardinia, Italy! This vacation includes round trip airfare to Sardinia, a hotel room for five nights, and a VIP tour of the Sella & Mosca winery. This prize package is valued at $4,850! Enter by December 31, 2011 for your chance to win! Good luck!

Enter the Monster Energy Drink Gears Of War 3 Sweepstakes for your chance to win one of five Grand Prizes! Each Grand Prize winner will receive a limited edition Xbox 360 Gears of War 3 console which includes two limited edition Gears of War 3 wireless controllers, a 320 GB hard drive, an Xbox 360 headset, an Xbox 360 composite A/V cable, and a Gears of War 3 video game. They are even giving away fifty First Prizes which consist of a Gears of War 3 video game! Enter today for your chance to make the gamer in your household happy! You have until October 2nd for your chance to win!

If you are searching for a 2nd summer, then look no further! Enter this Travelocity sweepstake on Facebook by September 30th for your chance to win a Travelocity vacation for four to Orlando, Florida. This prize package includes round trip airfare for four and four nights in a hotel! Enter today for your chance to win! Good luck to you!

Give me a “Yee Haw!” Enter the Chevrolet Has Your Ticket To Nashville Sweepstakes by October 21st for your chance to win a trip for two to the 2011 CMA Awards! This prize package includes round trip airfare for two to Nashville, an overnight stay in a hotel in Nashville, ground transportation to and from the airport/hotel, and two tickets to the 2011 CMA Awards! Best yet, get your chance to watch some of Country Music’s finest and enjoy Brad Paisley and Carrie Underwood as they host this year’s ceremony. Good luck! May you win the prize!

If you are a foodie or simply like kitchen goodies and gadgets, then you will certainly want to check out the Shop Epicurious Sweepstakes. Enter by November 2nd for your chance to win the ultimate kitchen shopping spree of $5,000 to spend at Shop.Epicurious.com! Enter now for your chance to win!