Flip Side Festival of the Arts

Join us on Saturday, September 12th, 2026 from 3-9 as we celebrate the end of our garden season by enriching downtown South Milwaukee with music and art. This 3rd annual community event not only showcases the local talent scene, but also serves as a crucial fundraiser to maintain our programming. By attending, you’re helping us continue our mission to transform the community through activism.

Apply to vend at Flip Side 2026

Click HERE

Flip Side Festival Official T‑Shirt Design Contest

What you’re creating

Design a bold, wearable graphic that captures the energy of the Flip Side Festival and the Milwaukee Avenue neighborhood. The winning design will be printed on this year’s official festival shirts worn by attendees, volunteers, and supporters throughout the event and beyond.

Prize and rights

The winning artist will receive a cash prize of $250.
2 Runners up will receive gift cards to neighborhood small businesses.
Artists retain full ownership of their original artwork.
By accepting the prize, the winning artist grants Growing South Milwaukee a limited license to use the design on 2026 festival T‑shirts and related promotional materials for this year’s event only (website, social media, flyers, etc.).
Any additional printing (e.g., future years or other merchandise) will require a separate agreement with the artist.

Eligibility

Open to artists in the South Milwaukee / Greater Milwaukee area.
Up to 3 designs per artist.
Artwork must be original, not previously used commercially, and suitable for T‑shirt printing (high contrast, readable, and a limited color palette is recommended).
Free to enter — no submission fee.

Submission guidelines

Submit by June 15, 2026 to growingsm@gmail.com with subject line: “Flipside T‑Shirt Submission – [Your Name]”.
Include:

Full name, contact info, and website/socials (if any).
Short description of the design concept (1–3 sentences).
High‑res JPG/PNG or vector file (300 dpi or scalable).
Optional: preferred shirt color(s).

Selection process

Submissions will be reviewed by festival organizers.
Finalists will be shared for community voting online and in person.
The winning design will be announced August 1, 2026.

Questions?
Contact Leah at growingsm@gmail.com
414-419-4166

Key dates

Milestone	Date
Call to artists opens	April 1, 2026
Submission deadline	June 15, 2026
Finalists announced	June 30, 2026
Public voting opens	July 1, 2026
Public voting closes	July 31, 2026
Winner announced	August 1, 2026
Flip Side Festival	September 12, 2026

Sponsor Flip Side and be part of something special

This volunteer-driven event brings art, music, and culture to downtown South Milwaukee every year. With the generous support of sponsors like you, we are able to present a high quality, community enrichment experience for our South Shore neighborhood — while raising critical funds for our nonprofit mission.

This year we need YOU.

We have put together a sponsorship package named after some of the greatest artists in history —
because great art deserves great support: