Winter Bluegrass Festival
Four day event in Charlottetown in March

The Prince Edward Island Bluegrass and Old Time Music Society will present the 2026 PEI Winter Bluegrass Festival from March 19–22 at the Delta Prince Edward by Marriott in Charlottetown.
The Winter Festival is celebrating over 80 years of bluegrass music, with a four-day event that builds on the success of the festival’s inaugural edition in 2023.
The festival will pay tribute to the genre’s roots, from Bill Monroe’s landmark 1945 appearance on the Grand Ole Opry stage to bluegrass’ influence on contemporary music. Audiences can expect performances that highlight both the history and the ongoing evolution of the music.
In true Maritime spirit, the event draws on local heritage, weaving together bluegrass with its Irish and Scottish threads—the very influences that sparked the genre’s birth deep in the mountains of Appalachia. Leading that musical fusion is the Tim O’Brien Band, known worldwide for blending Appalachian, Irish, Scottish, and old-time traditions and ancient tones of the old world into a sound all his own. From his West Virginia upbringing to international acclaim with his band Hot Rize, O’Brien’s career embodies bluegrass’ global reach and timeless appeal.
In addition, the festival has established a new partnership with Holland College’s School of Performing Arts, contributing to the introduction of bluegrass music within the institution’s curriculum. A series of workshops, presentations, and in-class jam sessions were held in preparation for a special appearance by Mr. O’Brien, who will lead an intimate workshop at the school itself.
The Tim O’Brien Band will anchor a lineup that includes Old Man Luedecke, Blue Meadow, The Janet McGarry Band, Shane Pendergast Trio, Bluegrass Tradition, The McMillan’s Camp Boys, The Stiff Family Band, Bad Hoss, the Holland College SOPA Student Band, The Sunny Mountain Gals, and more. Long-time fans and diverse music enthusiasts are encouraged to take part in this unique winter gathering of musicians, supporters, and genre-bridging performances.
Activities begin March 19 with a band-led welcome event and open mic jam. Friday’s schedule features the Bluegrass Market, the festival’s own vendor Music Row, combining nearly 20 local artisans and vendors with live music, leading into main-stage performances and a Slow Jam workshop with Ivan Rosenberg. On Saturday, a fireside chat, “Pioneering Women in Bluegrass Music,” hosted by The Sunny Mountain Gals with guests Barbara Martin Stephens and Betty Hartford, will kick off a full day of stage shows and late-night jam sessions. Festivities conclude Sunday with a Gospel Brunch hosted by the Stiff Family at Water’s Edge Restaurant.
Festival amenities include an instrument check service and extended hours at the hotel restaurant to accommodate performance schedules. Holland College SoPA students and festival volunteers will be on site to assist attendees.
