Winter Bluegrass

The 2026 PEI Winter Bluegrass Festival returns to the Delta Prince Edward by Marriott in Charlottetown from March 19–22. Presented by the PEI Bluegrass and Old Time Music Society, this four-day celebration marks more than 80 years of bluegrass heritage—promising non-stop pickin’, strummin’, and Island hospitality. Building on the success of its 2023 debut, the festival’s 2026 edition is set to draw musicians, fans, and jam enthusiasts from across the Maritimes and beyond, with the Tim O’Brien Band headlining.

Over a distinguished career spanning five decades, Tim O’Brien has achieved widespread recognition as an accomplished instrumentalist and vocalist with the acclaimed bluegrass group Hot Rize. His songwriting has garnered international recognition, with his compositions recorded by Kathy Mattea, Garth Brooks, New Grass Revival, Dirks Bentley, and many others. Grammy Award-winning O’Brien has maintained a prolific recording career both as a solo artist and in collaboration with notable musicians including Darrell Scott, Dirk Powell, Sturgill Simpson, and closer to home—Old Man Luedecke. Members of his band include his wife, Jan Fabricius; Mike Bub, a legendary bassist with the Del McCoury Band; and Nashville’s Shad Cobb on fiddle, who has worked with Willie Nelson, Steve Earle, and Mike Snider.

Organizers say this year’s lineup will appeal to longtime bluegrass fans and first-time festival-goers alike.

The festival begins on March 19 at Water’s Edge in the hotel lobby with performances by Roger Stone and the Shantytown Trio, followed by an open mic session and evening jam. March 20 and 21 include mainstage performances followed by late night all-star jams in the lobby, where music enthusiasts can rub shoulders and jam with industry luminaries. Both days will also feature the festival’s Merchant Row, showcasing the Island’s finest artisans and craft makers. Merchant Row runs Friday from 1–6 pm and Saturday from 10 am–6 pm. 

Mainstage events include the Tim O’Brien Band, along with other bluegrass and traditional Maritime favourites such as Old Man Luedecke, the McMillan’s Camp Boys, the Shane Pendergast Trio, Bluegrass Tradition, Blue Meadow, the Janet McGarry Band, The Sunny Mountain Gals, The Stiff Family Band, Bad Hoss, and Holland College School of Performing Arts.

On Saturday morning, musician Ivan Rosenberg will lead a “Slow Jam” workshop, guiding participants through the Nashville Number System and helping them gain confidence for group jams.  

A special highlight on March 21 is the “Pioneering Women in Bluegrass” mainstage event, featuring Betty Hartford and Barbara Martin Stephens, hosted by the Sunny Mountain Gals. Betty began singing old-time songs for her family in Missouri at age six. By age 14, she was co-hosting a live gospel program on KTCB-Malden with her uncle Jimmy Payne. After moving to St. Louis, she met her future husband, John Hartford. Barbara’s journey led her to bluegrass legend Jimmy Martin at age 17. She became his booking agent—the first woman to hold that role on Music Row. Though their paths differed, both women built remarkable lives shaped by music and love, experiences they now bring to the festival stage. Stephens will also have copies of her book, The People and the Music—Country and Bluegrass That Is!, available for purchase and signing following the session.

The festival concludes with a Sunday morning gospel brunch featuring The Stiff Family Band. 

A special festival brunch buffet will be offered at Water’s Edge on Saturday and Sunday. A secure instrument check area will be available, with Holland College School of Performing Arts students and volunteers on site to assist attendees.

Visit peibluegrass.ca/winter-festival for tickets and program updates, or follow the festival on Facebook.