Timberland PRO - $10,000 Sweepstakes

The Timberland PRO $10,000 Sweepstakes runs from January 1, 2025, to December 31, 2025. It is open to legal residents of the 50 U.S. states, D.C., and Canada (excluding Quebec), aged 18+ (or the age of majority in their jurisdiction). Employees of Timberland and associated entities, as well as their immediate family members and household members, are not eligible.
To enter:
- Purchase Method: Buy any Timberland PRO apparel or shoes with a promotional tag, visit dayinmyshoes.com or Head2ToePRO.com, complete a survey, and submit the entry form.
- Mail-in Method (No Purchase Required): Send a handwritten entry with your details to “Timberland PRO Sweepstakes,” PO Box D, Social Circle, GA 30025-1559, U.S.A.
Grand Prize (1):
- $10,000 USD (awarded as a check)
The winner will be randomly selected on January 9, 2026, and contacted by email or phone. Canadian winners must answer a skill-testing question to claim the prize.