Win a Dream Tailgate Trip in the 2025 Destination: Tailgate Sweepstakes

The 2025 Destination: Tailgate Sweepstakes is officially here—and it’s one of those under-the-radar promotions that can actually change your weekend plans for good. Imagine scoring a fully paid three-day trip for you and your crew to any major city in the continental U.S., complete with flights, hotel, and a bonus $250 gift card for tailgate snacks or souvenir splurges. If you live in one of the eligible midwestern or southern states, this is your shot to travel and tailgate like a VIP—no purchase required.

This giveaway is open now through October 28, 2025, and it’s hosted by Associated Wholesale Grocers, the same folks who fuel your favorite local grocery stores. Before you scroll away, let’s break down what makes this sweepstakes worth your time (and how to make sure your entry actually counts).

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Prize Breakdown

There are two prize tiers—and the numbers are wild.

Grand Prizes (8 total):
Each division of Associated Wholesale Grocers will award one lucky winner a $3,500 trip for four to any major U.S. city. That includes:

• Round-trip airfare for four
• Two nights in a hotel (standard accommodations)
• A $250 prepaid gift card to cover your tailgate, meals, or game-day merch

Each Grand Prize is valued at roughly $3,500, so across all eight divisions, that’s $28,000 in total dream-trip value up for grabs.

Second-Place Prizes (approx. 3,096 total):
Over 3,000 winners will snag a $50 grocery certificate to their local participating store. That’s cash-back you can actually spend on your next food run—no gimmicks. These will be awarded weekly throughout October (October 8, 15, 22 and 29).

All in all, the total prize pool adds up to a jaw-dropping $154,800.

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What You Can Do with the Prize If You Win

Let’s be honest: a free trip and a prepaid gift card are an influencer-level glow-up moment. You could:

• Fly out to see your favorite team play on their home turf and host the most aesthetic tailgate spread imaginable.
• Turn it into a long-overdue girls’ getaway or a family reunion weekend in a bucket-list city like Nashville, Chicago, or Austin.
• Or skip the sports scene entirely and explore rooftop bars, barbecue joints, and concerts—because the “tailgate” can be whatever vibe you want it to be.

If you land one of the $50 grocery certificates, you’re still winning. That’s free fuel for your next tailgate bash, Halloween party, or meal-prep marathon.

This sweepstakes is tailor-made for people who love to host, travel, or just win cool stuff for being in the right zip code.

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Q&A

Is this legitimate?
Yes—100 percent. The sweepstakes is sponsored by Associated Wholesale Grocers, Inc., headquartered in Kansas City, KS. It’s completely legitimate, and entries are handled through their official website at www.destinationtailgate.com.

How many entries are allowed?
It’s one entry per person, per day—whether you enter online or by mail. That means you can rack up multiple entries if you come back daily during the entry period (October 1 – October 28, 2025).

Are there bonus entries?
No, this one keeps it old-school. One entry per day, no referral system or social shares required.

How many prizes can you win?
You can win only one prize total—either a Grand Prize or a Second-Place Prize per household.

Who can enter?
This sweepstakes is open to residents of select states in the central and southern U.S. (think Alabama through Wisconsin). You must live within 45 miles of a participating Associated Wholesale Grocers store and be at least 18 years old with a valid driver’s license. It’s void in New York, Florida, and Rhode Island, so check your ZIP before entering.

When does it end?
Entries close at 11:59 P.M. CT on October 28, 2025. Grand Prize drawings happen around November 1, and Second-Place winners are drawn weekly.