Dynamic Old Town New Folk Season Brings Musical Magic to Key West in 2026

​America’s Finest Folk and Americana Artists Shine Indoors and Under the Stars

[Key West, FL] — The Studios of Key West is turning up the volume this winter with Old Town New Folk, a live music series built for people who love a great night out — even if “folk” isn’t usually their thing.

This contemporary folk series is smart, lively, and full of personality: music with sharp turns, great stories, and artists who know how to take an audience along for the ride. Each performer plays twice — once in the Helmerich Theater and once under the stars at Hugh’s View Rooftop — turning winter nights in Key West into something electric, with close-up performances and the kind of shared experience that makes live music memorable.

John McCutcheon (February 3–4) brings the kind of show that feels like you’ve been invited into a long, lively conversation — funny, generous, and full of heart. With more than 45 albums and a legendary command of the hammered dulcimer, his songs draw from real people and real lives.

Rachael Sage (February 17–18) brings her bold, genre-hopping sound to the series. An early pioneer of independent music-making, Sage blends folk, pop, rock, and jazz with theatrical flair. Her performances are intimate and surprising, often shifting gears mid-song and keeping audiences happily guessing.

Jon Langford (March 3–4) follows with shows shaped by a career that has zigzagged through punk, alternative country, and indie rock. A founding member of the Mekons and a longtime fixture of Chicago’s music scene, Langford delivers performances that are sharp, funny, story-driven, and refreshingly unpolished.

Jake Shimabukuro (March 10–11) brings his jaw-dropping artistry to Key West. Best known for sparking a global ukulele revival after a viral performance of “While My Guitar Gently Weeps,” Shimabukuro moves effortlessly from classical to rock to jazz, often leaving first-time listeners grinning in disbelief at what a ukulele can do.

The season concludes with Ricky Skaggs with Sharon White (March 24–25). A Grammy Award-winning legend who first appeared on national television as a child, Skaggs brings decades of mastery to bluegrass and country music. Joined by White’s luminous harmonies, the performances promise warmth, virtuosity, and deep roots — played with joy rather than nostalgia.

Hugh’s View Rooftop offers sweeping island views and open-air nights under the sky, while the Helmerich Theater delivers an up-close indoor experience where every note lands. Whether indoors or under the stars, Old Town New Folk is designed for listening, laughing, and leaning in.
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Old Town New Folk tickets are available now at tskw.org or by calling 305-296-0458.