October 10, 2025
DASH INTO HALLOWEEN: ENTER YOUR PET IN OUR COSTUME CONTEST!
It’s that time again – Dash, The Pineapple Pup, is back with the 9th Annual Costume Contest, and your furry friend could score some tail-wagging prizes.
How to enter:
- Follow @staypineapple and like our Costume Contest post on Instagram
- Post a brand-new photo or Reel of your dog in their Halloween best on Instagram
- Tag @staypineapple and use #pineapplepupcostumecontest25
Quick notes: Make sure your account is public and DM us the original photo/video of your post so we can use it in case you’re a finalist!
Entries close 10/28/25 at 11:59 PM PT.
Prizes:
- Grand Prize: Two-night stay at any Staypineapple hotel + swag bag
- 2nd, 3rd & 4th Place: Staypineapple swag bag
Our panel of judges will select the top 4 finalists, then it’s up to the audience to vote! Winners announced around 11/4/25.
Click here to read the official contest rules.
Need some ghoulishly great inspiration? Check out last year’s winner, Lulu, as the cutest kissing booth!
We’re howling with excitement to see your dog’s cutest, spookiest and most creative costumes this year – good luck!