Travel Oregon Win a Luxury Portland Escape for Two Sweepstakes (Win Ritz-Carlton Stay + Timbers/Thorns Tickets, ARV up to $3,346) – Ends August 31, 2026

Travel Oregon is giving away a luxury weekend getaway for two to Portland — including a 2-night stay at The Ritz-Carlton, two tickets to a Portland Timbers or Thorns match, and a dining gift certificate to the iconic Jake’s Grill. The total prize package is worth up to $3,346, and entry is a simple one-time form fill open to U.S. and Canadian residents 21 and older.

What Is The Travel Oregon Portland Escape for Two Sweepstakes?

This sweepstakes is run by Travel Oregon, the state’s official tourism authority, as part of their 2026 Summer Sweepstakes campaign. The prize is built around what makes Portland genuinely worth visiting: a luxury hotel stay with spa access at The Ritz-Carlton, live soccer energy at a Portland Timbers or Thorns FC match at Soccer City USA, and a meal at Jake’s Grill — a Portland institution known for its steaks, seafood, and lively bar atmosphere.

Everything is designed to be walkable with no car required, making it an ideal city escape for anyone who wants to experience the best of Portland in one long weekend. Travel Oregon is a credible, government-backed sponsor, and the prize package covers the full experience from hotel to sport to dining. If you’ve been looking for an excuse to visit the Rose City, this is it.

READ MORE: HERE’S OUR LIST OF THE BEST CONTESTS AND SWEEPSTAKES

Travel Oregon Portland Escape for Two Sweepstakes Details

• Start Date: April 20, 2026 at 12:00:01 a.m. PDT
• End Date: August 31, 2026
• Eligibility: Legal residents of the United States and Canada, 21 years of age or older; void in Puerto Rico, Quebec, and where prohibited by law
• Entry Frequency: One (1) entry per person
• Total Winners: 1
• Prize ARV: $2,946 – $3,346
• Sponsor: Travel Oregon
• Official Rules: PDF via traveloregon.com
• Entry Page: forms.traveloregon.com/portland-escape-for-two

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How to Enter the Sweepstakes

• Visit forms.traveloregon.com/portland-escape-for-two
• Fill out the entry form with your email address, name, country, state, postal code, and birthdate
• Agree to the official rules and submit — that’s it
• Must be 21 years of age or older and a resident of the U.S. or Canada (excluding Puerto Rico and Quebec)
• Limit of one entry per person

Entry takes under two minutes and also gives you the option to subscribe to Travel Oregon’s newsletter — totally optional, but a good resource if you’re planning an Oregon trip.

Win the Prize

One (1) Grand Prize Package — ARV $2,946 to $3,346:

• (1) $2,246 Ritz-Carlton gift certificate — redeemable toward a 2-night stay at The Ritz-Carlton Portland, including hotel and spa
• (2) Tickets to a Portland Timbers or Portland Thorns FC match — winner may indicate event preference; ARV $400 – $800
• (1) $300 Jake’s Grill gift certificate — iconic Portland restaurant known for steaks, seafood, and a lively bar

Everything is located within walking distance in downtown Portland — no car needed.

Is This Sweepstakes Worth Entering? (Quick Take)

This is a premium, experience-focused prize from a reputable tourism sponsor — not just a gift card. The Ritz-Carlton Portland, a Timbers or Thorns match at Providence Park (one of the most famous soccer atmospheres in North America), and dinner at a Portland landmark make for a genuinely memorable trip. The single-entry format and U.S./Canada-wide eligibility means the odds aren’t terrible for a prize this valuable. Anyone who enjoys travel, live sports, or fine dining should take the two minutes to enter before August 31.

Pro Tips to Increase Your Chances

• Enter now rather than later — with single-entry format, there’s no benefit to waiting; earlier entry means more time in the pool
• Use an active email address — winner notification comes via email, so use one you check regularly
• Canadian residents are eligible — unlike most U.S.-focused sweepstakes, this one is open to Canadian residents (except Quebec), which is a notable perk worth sharing with friends across the border
• Indicate your match preference — the winner can express a preference for Timbers (MLS) vs. Thorns (NWSL), so think about which you’d prefer when you win
• Optional newsletter signup — subscribing to Travel Oregon’s email list during entry is optional and won’t affect your chances, but it’s a solid resource if you’re planning a trip to Oregon regardless

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