Fright-Fall 2025 Daily Calendar

Fright-Fall 2025 Daily Calendar

In 2021, we had the idea of creating a small Halloween drawing challenge for artists and designers. We put together our first list of spooky prompts, made some simple rules, added some fun prizes, and Fright-Fall was born.

Little did we know that thousands of artists, spanning from novices to professionals, would participate. It soon became one of our treasured RetroSupply rituals.

 

Each October, our social media feeds would overflow with skulls, vampires, gravestones, obscure horror movie references, and clever Halloween puns.

Now in its fifth year, the Fright Fall Drawing Challenge is nearly here, and we'd love for you to be a part of it.

The Fright Fall Drawing Challenge, an annual art challenge by RetroSupply that takes place throughout October, features 31 prompts.

Participants are encouraged to use any style or medium they prefer, whether it's a sketchbook, iPad, Procreate, Photoshop, Illustrator, markers, or a simple ballpoint pen. The primary goal is to create, share, and connect. No pressure. Just fun.

This year's Fright-Fall 2025 is special because it commemorates the challenge's fifth anniversary. We are reverting to the original prompt list from 2021, crafted by our talented friend and artist, Robin Banks.

RetroSupply's Fright-Fall Drawing Challenge 2025 prompt calendar

The official 2025 Fright-Fall calendar featuring the original prompts from 2021.

The event will showcase the original artwork that inaugurated the challenge and pay homage to the remarkable community that has transformed the challenge into a global tradition.

If you've been with us since the first Fright Fall, this year will feel like a double dose of spooky nostalgia. For first-time participants, consider this your warm welcome to the party.

How to Join the 2025 Fright-Fall Drawing Challenge

Joining Fright Fall 2025 is easy and signing up officially enters you into the challenge (and the prize drawings).

Here’s how to get started:

  1. Sign up for the Fright Fall 2025 email list. This is your official entry into the challenge and what qualifies you to win prizes like an iPad Pro, Apple Pencils, and more. Plus, it makes it easier for us to find, share, and feature your artwork during the event.
  2. Grab your free goodies. After you sign up, download the Fright Fall Drawing Challenge prompt PDF to hang in your workspace or keep handy on your device. You’ll also get access to our free digital drawing tools, perfect if you want to give your work that classic RetroSupply look (though they’re totally optional).
  3. Start drawing October 1st. Each day, tackle the daily prompt in whatever style or medium you love—digital, traditional, or mixed.
  4. Share your artwork. Post your creations on Instagram using #FrightFall2025 and tag @retrosupply. Every post is a chance to win prizes, get featured in our emails and social feeds, and be part of the growing Fright-Fall community.
  5. Watch for community updates. Throughout September and October, keep an eye on your inbox. We may launch a dedicated community space to make it even easier to share, get feedback, and celebrate each other’s work.

For those seeking to maximize their Fright-Fall experience, consider these expert tips:

  • Embrace experimentation and fun over perfection.
  • If your schedule is tight, try completing two or three prompts over the weekend.
  • Take advantage of the opportunity to explore new tools and techniques.
  • Engage with the creative community by following the hashtag, commenting on fellow artists' work, and forming new connections.

Thanks for Making Fright-Fall Special

From a modest concept in 2021 to a global drawing challenge, Fright Fall has flourished thanks to your participation. We've witnessed artists enhance their skills, expand their audiences, and, most importantly, find pleasure in the act of creation. That's what this endeavor is all about.

Thank you for making October our most beloved month of the year. We eagerly anticipate witnessing your creations for Fright Fall 2025. Let's make October a spooky, creative, and nostalgic month together.

P.S. Don't miss out on The Midnight Vault

Stay tuned for the launch of the Midnight Vault, where premium retro Halloween design resources await. Subscribers will gain access to a collection of eerie fonts, vintage textures, and brushes, along with exclusive flash sales.