12 Free Writing Contests to Enter This Winter (2024-2025)

Freewriter Mike Somerby left a lucrative marketing career in e-commerce to start a print-only literary magazine by and for Montanans. Yes, you read that right.

We sat down with Mike to find out how ... and why.

Mike Somerby identifies as a writer — with some reservation.

"I think all who write are 'writers,'" he says, "even if the writing itself amounts to a simple letter to a friend or a personal journal entry."

We couldn't agree more. And we're thrilled that this particular writer writes his essays on Freewrite. Maybe that's why we felt comfortable asking him:

What inspires a professional brand marketer to leave his 9-5 and jump feet-first into the literary world of Bozeman, Montana?

Luckily, he was happy to tell us.

AC: Before we get into the lit mag, it actually isn't your first foray into the literary community, right?

MS: For about ten years — the lion's share of my professional chapter — I worked, in some capacity, as a brand marketer. Last spring, while enduring a particularly grueling stint as CMO for a Montanan e-commerce brand (yes, those exist), I found myself revisited by the remarks of an old journalism school professor: from his perspective, journalism students who apply their storytelling talents toward PR and marketing have crossed over to "the dark side."

While I find this a touch heavy-handed, I get the point, and I believe his notion resurfaced to meet the moment: we live in a world sorely hurting for analog (human) creativity and high-quality longform.

So I quit, traveled west with my dog in a 1986 U-Haul I'd converted into a camper, and plotted.

Step one: I founded Pulphead, a lounge (named after John Jeremiah Sullivan’s seminal 2011 essay collection) where Bozeman writers commune and grind out their prose until 2 a.m. Entry is a flat $5, which comes with unlimited drip coffee and tea.

Step two: leverage the Pulphead regulars and its online following to secure contributors for my new literary magazine, ANEMONE. Thus far, everything is going to plan.

We live in a world sorely hurting for analog (human) creativity and high-quality longform.

AC: Why do you think it's so important to create and preserve these spaces for authentic writing?

MS: Writing is a solitary act. Nonetheless, younger generations, in particular, struggle to forge IRL community in the way older generations might understand as an ordinary facet of being human.

By building a space that is as homey as it is supportive of their literary interests, we’re not only helping these individuals find their birds of a feather, but also providing them with a dojo that mandates setting aside blocks of time away from phones, home lives, and the other distractions. Win-win?

Incidentally, Livingston boasts the highest per-capita concentration of professional writers anywhere in the country. Couple this with another statistic — that Montana has more bookstores per capita than any other state — and it becomes clear southwest Montana is as fertile a place as any to invest in literature and its related industries.

AC: That's so interesting. What have you learned from being in community with creatives in Bozeman?

MS: In terms of writing, I've learned plenty. What has excited me most, however, is what I’ve learned from a small group of Indigenous women who come to the shop to write poetry and make beaded clothing in the traditions of their respective tribes (most notably, Crow, Cheyenne, Shoshone).

This is a group I’d otherwise have limited opportunity to engage with outside of Pulphead, and learning about their traditions, beliefs, hopes — even a little vocabulary — through firsthand conversation has proved incredibly edifying.

AC: And you mentioned you've seen Freewrites pop up in Pulphead. You use one, right?

MS: Yes. About seven years ago, not long after moving to Montana from New York, I purchased an Olivetti Lettera 32 typewriter from eBay. It appeared that a romanticizing of my newfound remoteness had rekindled my interest in writing.

I loved the mechanical feel and distraction-free interface, but the inability to edit line by line proved a notable annoyance for a mind habituated to modern computers. A few years down the road, some digging for alternatives led me to a blog post about smart/electronic typewriters. Voilà.

I purchased a Freewrite Gen3 Smart Typewriter, and I've been hooked ever since.

AC: That's awesome. So tell us about ANEMONE. What is it?

MS: ANEMONE is a print-only magazine (printed in a traditional broadsheet newspaper format). As for for theme, broadly, the world as told by Montanans. Short fiction, creative nonfiction, poetry, reportage, photography, and visiual illustrations comprise the submission categories.

AC: Print-only!

MS: Print is only dying because we let it.

AC: Is there a story about the name?

MS: Most people know the word anemone to describe a family of flowers — a 200-plus-species family of buttercups, comprising varieties both wild and domesticated. Dubbed “windflowers,” their delicate petals are said to blow open in the breeze; the ancient Greek word anemos means “wind.” I was drawn to the metaphorical value of beauty and how it can be revealed to us through an invisible force.

To add another layer, when I was a boy my father and I would spend weekends at the beaches north of San Francisco, where I was born and raised until I was seven. We would study the massive turqoise, kelly green, and purple sea anemones clinging to rocks left exposed by the receding Pacific tides (as to why, I can't say, outside of them looking funny, almost alien). A good memory.

Finally, “Anemone” is the name of an exquisite song by The Brian Jonestown Massacre, an irreverent and controversial rock band led by Anton Newcombe, an obsessive creative who rejects the surrender of culture and art to commercial interests. The track has a hold on me. It's like a portal to another era.

AC: Why do you think this sort of analog creativity is important?

MS:  I'm told the unending deluge of digital interface is leaving humans less and less capable of “deep work.” Will we ever know the difference?

Will we recognize what a society incapable of deep work looks like compared with those that came before it? Or will the transition manifest as a gradual degradation of quality, much as Coca-Cola was slowly, but surely, divorced from real sugar, such that to taste what Coke used to be like, one must order a Mexican Coke, still made with real cane sugar?

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

I prefer the former, and I suspect those who prefer the latter don't read or write much — life is a beautiful, taxing mess, and good writers find merit in this duality.

For me, analog perspective (and any creativity wrung from it) is rooted in continuity, tangibility, lived experience, slowness, spatial relation, nuance, emphasis on process, and grace for imperfection — antithetical to one of replicability, speed, binary outcomes, predictability, and optimization.

AC: Who is invited to submit to ANEMONE?

MS: We do limit submissions to Montanans, past and present, though we will feature writers from other states should the content of their writing bear an obvious relation to Montana — a requirement not imposed on Montanan writers.

All information regarding submissions can be found at www.anemonereview.com, along with all other facets of the magazine.

Love the Freewrite 500? Here are 3 more writing contests for competitive short fiction writers.

1) Writers' Hour Magazine Prompts

The London Writer's Salon (a global writing group — no London residence necessary!) regularly host a writing contest via their Writers' Hour Magazine. Want to know a secret? Their September theme is all about freewriting.

Join them for a free workshop, Introduction to Freewriting, on Thursday, September 3, and get all the details about the contest.

The winner of the contest will win something Freewrite-shaped. 👀

2) NYC Midnight Challenges

This organization (again, no affiliation with NYC necessary) regularly hosts short story contests. Their next challenge is all about writing a rhyming story.

Learn more and register here.

Note: NYC Midnight writing contests generally have a fee to enter.

3) Henshaw Press Short Story Competition

This short story competition is open to anyone over age 16. And the best part? There is a cash prize, and profits go to charity.

Learn more here.

PRESENTED IN COLLABORATION WITH

Calling all micro-fiction storytellers! 🏁

For the second year in a row, Freewrite is teaming up with Grant Faulkner, co-founder of the Flash Fiction Institute and author of The Art of Brevity, to bring you the fastest, most adrenaline-pumping writing event of the year.

Whether you're a seasoned writer or a creative rookie, the Freewrite 500 is your chance to rev up your imagination, write a 500-word story, and win big.

You do not need to own a Freewrite to participate.

[REGISTRATION CLOSED]

How It Works

🎟️ Fill out the form above to secure your spot. It's totally free. (You must register to participate.)

📖 Watch the free mini flash fiction lesson by Grant Faulkner, which includes the announcement of the prompt for the contest. WATCH IT HERE.

📝 You'll have the weekend to finish and submit your 500-word storybased on the prompt by end of day on Monday, August 17. Entries must be 500 words or less. The entry form is plain text. Any necessary formatting should be noted in [brackets]. [SUBMISSIONS CLOSED]

✏️ Our judging panel, led by Faulkner and made up of writers from the Freewrite team and the Flash Fiction Institute, will judge each piece based on: length (500 words), relevance to the prompt, and creativity.

🥇 NEW THIS YEAR: The panel will select three finalists, and then announce one grand prize winner.

All work must be submitted by 11:59 p.m. ET on Monday, August 17, 2026.

The Prize Pack

One winner will receive:

• Publication on the Freewrite blog and Flash Fiction Institute blog
• 1 Freewrite Traveler
• 1 hour-long one-on-one coaching session with Grant Faulkner
• 1 free Flash Gym session with the Flash Fiction Institute
  
• 1 Words Are Hard prompt deck
  
• A paperback copy of Set Your Story Free, the ultimate guide to freewriting
• A digital copy of the opening chapter of Grant Faulkner's book, The Art of Brevity

Second and third place writers will each receive:

• Publication on the Freewrite blog and Flash Fiction Institute blog
• 1 Freewrite Alpha
• 1 free Flash Gym session with the Flash Fiction Institute
• 1 Words Are Hard prompt deck
• A paperback copy of Set Your Story Free, the ultimate guide to freewriting
• A digital copy of the opening chapter of Grant Faulkner's book, The Art of Brevity

The Schedule

• Thursday, Aug 13: Lesson & prompt announcement
• Monday, Aug 17: Submissions deadline
• Monday, Aug 31: Finalists announced
• Monday, September 7: Grand prize winner announced

Questions? You can reach us at hello@getfreewrite.com.

Write on.

The Freewrite 500 Pit Crew 🏁 

Full contest terms and conditions