DOES YOUR PET’S HALLOWEEN COSTUME HAVE WHAT IT TAKES TO BE THE BEST?
Ten years of costumes, countless good boys and girls, and enough cuteness to fill the Instagram feed. Dash, The Pineapple Pup’s Annual Halloween Costume Contest is back for its 10th year, and he’s ready to see which pets can steal the spotlight!
Whether your pet is going for spooky, silly, stylish or downright ridiculous, dress them up and enter for a chance to win some serious prizes.
How to Enter
- Follow @staypineapple on Instagram.
- Post a NEW photo or Reel of your costumed pet on your l Instagram account. Your entry must be an in-feed post.
- Tag @staypineapple. Please note: If your account is private, we won’t be able to see your entry.
- Comment “ENTERED” on our official contest announcement post.
IMPORTANT NOTE: We want to see what YOU created! No AI-generated or AI-altered costume submissions will be accepted. Entries will be reviewed using detection software. Human + pet creativity only, please.
And Then There Were Four...
Our panel of Staypineapple judges will select the Top 4 finalists, who will go head-to-head in an Instagram audience vote.
The Top 4 will be revealed in a post on October 30, 2026, at 8 a.m. PST.
Ready to vote? Comment “VOTE” on the finalist announcement post, and we’ll automatically DM you a link to our voting form. You can vote unlimited times!
Winners will be notified by DM and announced on or around November 2, 2026.
The Prizes
- Grand Prize: A two-night stay at any Staypineapple hotel + a Staypineapple Swag Bag
- 2nd, 3rd & 4th Place: Staypineapple Swag Bag
Need a little inspiration? Check out last year’s grand-prize winner, pup Heaven, in her Trash Panda costume, which was truly a DIY masterpiece.
Now get crafty, get creative and show us what your pet’s got this Halloween!
Read the Official Rules + Guidelines here.