Winning Writers celebrates its 25th anniversary this year, having been founded in New York City in 2001, just prior to the 9/11 attacks. The organization relocated to Western Massachusetts in 2003 and has since provided a welcoming environment for authors of varied backgrounds and experiences.
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Adam Cohen and Jendi Reiter serve as President and Vice President, respectively. The contests run by Winning Writers are notably competitive. In the last contest year, the Wergle Flomp Humor Poetry Contest saw 4,825 submissions, while the North Street Book Prize received 1,734 entries. The Tom Howard/John H. Reid Fiction & Essay Contest garnered 1,757 submissions, and the Tom Howard/Margaret Reid Poetry Contest logged 2,471 entries. The majority of these contests, apart from the Book Prize, are judged anonymously.
Winning Writers is dedicated to offering substantial prizes. For the upcoming 2027 North Street Book Prize competition, a total of $23,500 will be awarded, alongside $5,100 for the Wergle Flomp Humor Poetry Contest, and $12,000 each for the Tom Howard/John H. Reid Fiction & Essay Contest and the Tom Howard/Margaret Reid Poetry Contest. Notably, a single poem in the latter contest can win $3,500.
B.J. Buckley, the 2014 Margaret Reid Prize winner, highlighted the contest's commitment to recognizing less mainstream poets, stating that it seeks to elevate those who often are not seen, describing them as "ordinary people who love poetry and write it seriously."
The North Street Book Prize is among the largest competitions for self-published and hybrid-published books, offering a grand prize of $10,000. Participants can also opt to receive free feedback on their submissions, underscoring Winning Writers' mission to support often underserved writers. Teresa Tennyson, the 2025 North Street grand prize winner, encourages indie authors to enter, emphasizing the contest's legitimacy and the organization’s generosity.
The Wergle Flomp Humor Poetry Contest is unique in its lack of an entry fee, originally created to parody vanity contests that provide frivolous praise for submissions. Today, it celebrates humor and satire in poetry.
Founded by Harvard graduates Jendi Reiter, an author of nine books, and Adam Cohen, former circulation director at The Atlantic, Winning Writers is known for its author-friendly approach and exceptional customer service, ensuring that issues are addressed swiftly and refunds are processed rapidly. The organization maintains a robust communication network, allowing customers to reach out via email and a toll-free number.
Around 63,000 poets and writers subscribe to Winning Writers' monthly newsletter, which features contest announcements, resources, and writing advice. Subscribers also gain access to The Best Free Literary Contests, an extensive online database of over 200 no-cost contests. Winning Writers has been recognized in Writer's Digest's "101 Best Websites for Writers" from 2015 to 2019 and in 2022 to 2026, receiving accolades from Reedsy and the Alliance of Independent Authors.