Key details before you enter
- Type: sweepstakes
- Status: Active
- Organizer: Timberland, a division of VF Outdoor, LLC; administered by Probability LLC
- Area: United States, Canada
- Start: 2026-01-01
- End: 2026-12-31
- Prize or benefit: One $10,000 USD check.
- Purchase required: No
How to enter
- Find the promotion URL on an eligible Timberland PRO shoe or apparel tag, or use the handwritten mail-in method from the rules.
- Complete the survey and registration form if using the product route.
- For the no-purchase route, handwrite the required information on a 3-by-5 card and mail it as described.
- Wait for the random drawing scheduled around January 12, 2027.
Main requirements
- Be a legal resident of the United States, D.C. or Canada, excluding Quebec.
- Be at least 18 or the age of majority in your jurisdiction, whichever is older.
- Use either the Timberland PRO product survey entry route or the mail-in route.
- Respect the one-entry limit across all methods.
Prize and selection
One $10,000 USD check.
Selection: Random drawing around January 12, 2027.
Entry limit: One entry per person across all entry methods.
- Mail-in entries must be handwritten and postmarked by January 4, 2027.
- The prize is awarded as a $10,000 USD check.
- The nature of survey responses does not affect eligibility or odds.
Official sources and verification
Wynplay verified this promotion on 2026-08-23. The official source controls if terms change.
Quick questions
When does it end?
The published end date is 2026-12-31.
What can I win?
One $10,000 USD check.
Where are the official rules?
Use the official links on this page.