Back by popular demand is Pet Portrait Roulette 2026! With a donation of $25, get your pet drawn by the creative minds of our team members. Some staff and volunteers have the artistic skills worthy of running their own art studio…and for others, well, let’s just say it’s best they stick to being trusted animal caretakers. Regardless of who you get as your assigned ‘artist’ though, you’re sure to receive a treasured, one-of-a-kind rendering of your beloved companion (and maybe a giggle).

Participation is easy — simply click here for our donation page, enter your information and donation, and select “Pet Portrait Roulette.” Then pick out which photo you’d like to enter for the fundraiser and email it to office@winonahumane.org along with the pet’s name, your full name, how you wish to receive your portrait (in-person pickup, scanned & emailed, or mailed) and any other information you’d like us to have. If you choose physical mailing as your preferred option, include your address and an additional $5.

Send in your donation + photo by November 13th for a guaranteed return in time for a Christmas present! Otherwise, this will be a rolling fundraiser we’re happy to continue as long as community members are enjoying it.

Scroll through the gallery below to see some of the 2025 submissions!