OREO Wedding Cash Guess Sweepstakes – Win $1,000
The OREO Land Mass Sweepstakes puts a playful spin on cash prizes with a guess-based challenge that works nicely as a wedding budget boost idea. Two winners will each receive $1,000 in cash, making this a fun pick for couples who love quirky promotions and wouldn’t mind a little extra money for wedding plans, honeymoon extras, or newlywed expenses.
Who can enter
Open to legal residents of the 50 United States and the District of Columbia
Must be at least 18 years old at the time of entry
Limit of one entry per eligible person
Key dates
Starts: April 1, 2026
Ends: April 29, 2026
Draw date: May 6, 2026
Posted date: April 4, 2026
Entry frequency
Single entry
How to enter
Website entry
Visit Oreo.com/playfulsweeps during the promotion period and complete the registration form with your first name, last name, and valid email address. Then answer the multiple-choice question about how many OREO cookies it would take to cover the land mass of the United States. After submitting your form and answer, you will receive one entry.
Social media entry
Some eligible participants who are logged into Facebook, Instagram, or TikTok may receive an invitation through a sponsored post. If you see the ad, click the Sign Up button and complete the entry form with your first name, last name, valid email address, and phone number. You will also answer the same multiple-choice question before submitting your entry.
Prize details
Grand Prizes (2 winners)
Each winner will receive:
$1,000 cash in the form of a check
Winner selection
Two grand prize winners will be selected randomly on or about May 6, 2026 from all eligible entries received.
Rules snapshot
Open to eligible U.S. residents age 18 and older
One entry per person is allowed
Website entry is available to all eligible entrants
Social media entry is by invitation through sponsored posts only
Two winners will be selected by random drawing
Official rules control all final eligibility and prize details
This giveaway is hosted by its sponsor, not by us
Rules and Regulations: Read the Official Rules & Regulations.
