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A John Prine Christmas! at Colony Woodstock | December 20, 2026

By Nate Calloway · October 11, 2026

John Prine wrote “Hello in There” while walking a mail route in Maywood, Illinois, composing in his head long before he had a label or a reason to think anyone beyond his postal district would ever hear his songs. He was under 22 when he finished a lyric about an old man sitting alone by a window — a degree of empathy the world doesn’t usually hand to young men. That instinct for the overlooked is why his catalog holds the way it does, and why a room full of people in Woodstock gathering on a Sunday night in December to play his songs feels like something beyond tribute, more like upkeep of a tradition that still has work left in it.

About the Show

Colony Woodstock hosts the return of Eric Squindo’s annual “A John Prine Christmas!” on December 20. The evening draws from Prine’s catalog spanning his 1971 debut through 2018, with classics, obscure cuts, and holiday material including songs from his 1994 Oh Boy Records holiday album, performed by a curated ensemble Squindo assembles for the occasion. Squindo, a songwriter and producer who has spent the better part of a decade organizing tribute evenings across the Hudson Valley, launched his “Eric Squindo Presents” series in 2019; previous installments have focused on Townes Van Zandt, Tom Waits, the Basement Tapes, and Woody Guthrie. His format is built around what one profile described as “the intimacy of a living room session”: solo and ensemble performances, collaborative pieces, building toward a full jam session that closes the night with all the players on stage.

John Prine, who passed away in April 2020, recorded 18 studio albums and received multiple Grammy Awards, including a Lifetime Achievement Award, along with induction into the Songwriters Hall of Fame. A portion of proceeds from this show benefits the Hello In There Foundation, established by Prine’s family in 2021, which has provided $1.4 million in grants to more than 100 organizations addressing food insecurity, housing, addiction recovery, and immigrant and refugee services. The foundation takes its name from that same song Prine composed on his mail route, more than half a century ago.

Venue & Logistics

Colony Woodstock, at 22 Rock City Road in Woodstock, NY, is a historic hotel that opened in 1929 and describes itself as “The Smartest Rendezvous in the Catskills.” At 150 capacity, it is the kind of room where Prine’s songs, built for close listening, find the right conditions. Doors open at 6 p.m.; show runs 7 p.m. to 10 p.m.

Tickets

Tickets are $23 to $40. Buy tickets

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Concert Details

📅December 20, 2026
🕐7:00 PM
💰$23 - $40
ℹ️On Sale

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