Long before it became The House That Rocks Killington, the building now known as the Pickle Barrel was the Sugar Shack — a rustic 1960s dance hall where locals and skiers gathered while Killington was still finding its footing. It later became Showcase East, a quirky combination of movies, drinks and mountain-town nightlife.
Then came Jack Giguere. In one of the more colorful chapters of Killington lore, Giguere took over the property in 1971 after famously crashing his car through the front door. He repaired the entrance, renamed it the Pickle Barrel, and helped turn it into one of the defining nightlife spots on the Killington Road.
Music soon became part of the building’s identity. By the mid-1970s bands were playing what is now the Crow’s Nest, and over the decades the Pickle Barrel grew into one of Vermont’s best-known concert venues. Its stages have hosted everyone from Warren Zevon, Blues Traveler and The Roots to The Wailers, Wu-Tang Clan, Matisyahu, Reel Big Fish and Snoop Dogg.
In 1999, longtime manager and Giguere protégé Chris Karr purchased the club and gave it a new identity: The House That Rocks Killington. Under Karr, the Pickle entered another era of packed après shows, major touring acts and stories that have become part of local folklore — including Mac & Jamie’s legendary move to the Pickle in 2000 and two sold-out Snoop Dogg shows in 2011.
More than half a century after its earliest days, the Pickle Barrel is still doing what it has always done best: giving Killington a place to gather, dance, hear live music and make stories of its own.
1960s — The Sugar Shack
1971 — Jack Giguere renames it the Pickle Barrel
1976 — Live music takes hold in what becomes the Crow’s Nest
1999 — Chris Karr takes ownership; “The House That Rocks Killington”
2000 — Mac & Jamie help redefine Pickle après
2011 — Two sold-out Snoop Dogg shows
Today — 4 bars • 3 levels • 2 stages • 1 very long story
They’ve Played the Pickle
Snoop Dogg · Warren Zevon · The Roots · The Wailers · Wu-Tang Clan · Blues Traveler · Matisyahu · Candlebox · Gin Blossoms · Reel Big Fish · Deep Banana Blackout · and generations of Vermont and regional artists.
The building began as a rustic dance hall when Killington itself was still young, serving as a gathering place for locals and skiers. It later became Showcase East, which combined drinks and movies.
Multiple sources repeat the story that Jack Giguere acquired Showcase East after crashing his car through the front door, then repaired it and renamed it the Pickle Barrel. That is exactly the kind of anecdote I would feature prominently — perhaps even as a pull quote or timeline moment.
he Seabird Band was brought to Killington by Giguere in 1976 and was the first band to play what is now the Crow’s Nest.
The Pickle Barrel became much more than a ski-town bar. Documented and/or repeatedly cited performers include Warren Zevon, The Wailers, The Roots, Blues Traveler, Matisyahu, Candlebox, Gin Blossoms, Wu-Tang Clan, Reel Big Fish, Deep Banana Blackout and many others. Warren Zevon, for example, is independently documented there in the 1990s.
Chris Karr had first come to Killington as an 18-year-old ski bum, worked under Jack Giguere, became a manager, and ultimately bought the Pickle Barrel in 1999 and rebranded it as “The House That Rocks Killington.”
The Mac & Jamie story is fantastic history-page material. They played an unannounced show in the Pickle Barrel’s Crow’s Nest while associated with the Wobbly, were subsequently fired there, and then became a major draw at the Pickle. The Mountain Times later described that episode as a moment that changed Killington après.
Karr has told the story of calling an old connection who had become Snoop Dogg’s agent and asking whether Snoop would ever come to Vermont. The result was two sold-out shows at the Pickle Barrel. That absolutely belongs on the page. The venue’s reputation: the existing history page notes that Ski Magazine called the Pickle Barrel a “Living Legend” and a “Classic,” and that Snow Country Magazine ranked it among its Top 5 Favorite Bars in North America. Mountain Times has repeated those accolades as well. Still evolving: even during the pandemic era the space was being adapted — seated live music, a revised setup, and a Till I Die pop-up in the Crow’s Nest — which helps show that this isn’t a preserved relic; it has kept changing with Killington.
