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Molly Tuttle

Molly Tuttle is a Grammy-winning singer, songwriter, and virtuosic guitarist whose innovative blend of bluegrass, Americana, pop, and rock has made her one of the most dynamic artists in modern roots music. In 2025, she released her boldest statement yet, the critically acclaimed So Long Little Miss Sunshine, nominated for two GRAMMY® Awards—Best Americana Album and Best Americana Performance for the lead single “That’s Gonna Leave A Mark.” Recorded in Nashville with producer Mike Joyce (Orville Peck, Miranda Lambert, Lainey Wilson), the album marks Tuttle’s fifth full-length release and her most ambitious reinvention to date: a vibrant, deeply personal body of work rooted in self-acceptance and transformation. A highly decorated artist, Tuttle has been nominated for 5 GRAMMY Awards (including in the Best New Artist category) and earned back-to-back GRAMMY wins for Best Bluegrass Album with her band Golden Highway—Crooked Tree (2022) and City of Gold (2023)—becoming the first artist in the category’s history to do so. She is also the first woman to receive the IBMA Guitar Player of the Year award, alongside multiple additional IBMA and Americana Music Awards.
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There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.




