Celebrating 25 Years of Winning Writers in the Literary World

This year, Winning Writers stands proudly at the milestone of its 25th anniversary, reflecting on its remarkable journey since its inception in 2001. Founded in the vibrant atmosphere of New York City, Winning Writers was established just before the tragic events of September 11, and later relocated to Western Massachusetts in 2003. Throughout its existence, it has maintained a steadfast commitment to supporting a diverse array of authors and narratives, fostering inclusivity and understanding across various backgrounds, gender identities, and abilities.

A Competitive Arena for Literary Talent

Winning Writers is renowned for its challenging literary contests designed to highlight fresh voices in literature. The latest contest year saw an impressive number of submissions: 4,825 for the Wergle Flomp Humor Poetry Contest, 1,734 for the North Street Book Prize, 1,757 for the Tom Howard/John H. Reid Fiction Essay Contest, and 2,471 for the Tom Howard/Margaret Reid Poetry Contest. Notably, all contests—except for the Book Prize—are judged anonymously, ensuring fairness and integrity in the selection process.

Generous Prizes Foster Writer Engagement

In 2027, Winning Writers plans to award an impressive total of $23,500 in its North Street Book Prize competition, $5,100 for the Wergle Flomp Humor Poetry Contest, and $12,000 each for both the Tom Howard/John H. Reid Fiction Essay Contest and the Tom Howard/Margaret Reid Poetry Contest. The latter contest features a remarkable prize for a single poem, rewarding up to $3,500. As expressed by B.J. Buckley, a past Margaret Reid Prize winner, these contests not only elevate underrepresented poets but also celebrate the everyday creativity of ordinary individuals who pursue poetry alongside their daily lives.

North Street Book Prize: A Champion for Indie Authors

The North Street Book Prize is particularly noteworthy, recognized as one of the largest competitions for self-published and hybrid-published works, offering a grand prize of $10,000. Every entrant has the opportunity to receive feedback on their submission at no extra cost, which exemplifies Winning Writers' commitment to supporting all writers, including those who are often overlooked in the literary landscape. Teresa Tennyson, winner of the 2025 North Street Grand Prize, wholeheartedly encourages indie writers to enter, branding it as a genuine contest where people do win and where authors are genuinely valued.

Celebrating Humor Through Poetry

An exciting aspect of Winning Writers is the Wergle Flomp Humor Poetry Contest, which is notable for having no entry fee. Initially created to parody vanity contests that mislead entrants with false praise, it now celebrates light verse, parody, and humor poetry with enthusiasm. This contest has become a refreshing outlet for creative expression in a competitive writing environment.

Foundational Values and Services

Founded by the dynamic duo of Jendi Reiter and Adam Cohen, both enriched by their educational backgrounds at Harvard University, Winning Writers embodies a pro-author ethos that prioritizes exceptional customer service. They are committed to addressing issues that may arise during the entry process, quickly resolving any challenges and providing refunds for entry fees whenever necessary. Their open-door policy, accessible via email, mail, and a toll-free phone line, is a rarity in today’s literary services landscape.

The organization has garnered a substantial following, with 63,000 poets and writers subscribing to its monthly newsletter, which is a treasure trove of contest news, resources, literary advice, and comics. Notably, subscribers receive complimentary access to “The Best Free Literary Contests,” an online database featuring over 200 comprehensive profiles of free contests.