The woods outside Sterling, New York, have hosted music for more than thirty years. Sterling Stage Kamphitheater — that tree-canopied amphitheater south of Lake Ontario where Into The Pines and Sterling Stage Folkfest have drawn audiences who prefer their festivals intimate and their campsites close enough to hear the late-night jams — adds a new name to the calendar in 2026. Tommypalooza arrives Memorial Day weekend, and it carries with it the kind of story that turns a first-year festival into something the community already owns.
Tommy Ryan spent decades building the culture at Sterling Stage. He was the person who kept the fires going, who made sure the generators ran, who understood that a festival is not just a lineup but a place where people return to feel something they cannot find anywhere else. When Tommy passed away on Christmas Day 2025, the community that had grown up around Sterling Stage decided the best way to honor him was to do what he always did: put on a show.
The Festival
Tommypalooza runs five days, May 21 through 25, presented by Watts Music Group. The lineup carries thirty-one artists across the weekend, led by Ryan Montbleau, Sophistafunk, and the Hayley Jane Band — acts that understand the room, or in this case, the clearing. The South Catherine Street Jug Band, Naive Melody, Dinner & A Movie, and Dead & Friends round out a bill that leans into the jam, folk, and roots traditions Sterling Stage has always championed.
If you know Sterling Stage from Into The Pines or the old Folkfest, you already know the setting. The natural amphitheater does acoustic work that money cannot buy — the trees break the wind, the slope gives sightlines, and the canopy filters afternoon light into something that makes even a Tuesday sound check feel cinematic. Camping is woven into the experience. You pitch your tent in the surrounding woods and fields, and the distance between your site and the stage is measured in footsteps, not shuttle rides.
What to Expect
This is a community festival in the truest sense. The capacity is intimate — Sterling Stage does not do fifty thousand. The food comes from local vendors. The vibe runs closer to a family reunion with a really good house band than a corporate production with wristband tiers. If you have been to GrassRoots or Great Blue Heron, you understand the ecosystem. Tommypalooza operates in that same tradition, with the added weight of a community saying goodbye and thank you at the same time.
Tickets are available through Ticketleap. Grab them early — Sterling Stage events have a way of selling through once word gets out, and word about this one has been moving through Central New York since the announcement dropped.