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Darren Winston

Darren Winston

Head of Department


Darren Winston serves as Head of the Books, Maps & Manuscripts Department, and is Freeman’s representative for the New York, Connecticut, and Western Massachusetts areas. Born in Chicago and raised in New Jersey, Mr. Winston moved to New York City in 1988, and began his career as a vintage bookseller in 1995. He spent more than ten years selling at book fairs and flea markets, as well as privately, before opening his eponymous bookshop in 2009. Located in Sharon, CT, Darren Winston, Bookseller offered vintage books, prints, and fine art, and hosted in-store events including book signings and art shows. 

Prior to joining Freeman’s, Mr. Winston served as an Independent Consultant to the Fine and Rare Books Department of British luxury company Asprey, from 1999 to 2005, in their New York store. While at Asprey, he was the buyer for both the New York and Beverly Hills boutiques, and organized in-store readings with authors such as Salman Rushdie and Dominick Dunne. In 1993, he was a Creative Consultant for Columbia Records in New York, where he assisted in the repackaging of their 12-record Aerosmith back catalogue; in 1993, Mr. Winston sold his extensive collection of memorabilia, which he began amassing at the age of 14, directly to the band. 

When not bookselling, Mr. Winston plays guitar with the The Harlem Line Band. Since 2009, he has hosted the radio program “Darren Winston’s Book Report” for NPR-affiliate WHDD. He appeared in the 2014 documentary “The Paper Trail” on books and paper, and is a member of the Independent Online Booksellers Association and the Southern New England Antiquarian Booksellers. Mr. Winston lives in Connecticut with his wife Lucinda, son Jamie, and daughter Katie. The family travels frequently to Mrs. Winston’s native England and Scotland.