It doesn’t happen as often as it used to, but every once and a while, a naive tourist comes to Woodstock looking to visit the site of the legendary Woodstock Music and Art Fair of 1969.
Once a local told me that when he encountered these poor souls, he’d point to an abandoned field across from his storefront and watch the befuddled visitors try to make sense of how half a million hippies were fit there.
Who could blame these pilgrims of the arts? Though the festival wasn’t held here, the intersection of Woodstock and music culture is deep and legendary.
But to focus solely on the tie-dyed echoes of the town’s hippie heyday is to do a disservice to the thriving, thoroughly modern music scene the town enjoys today. Let’s take a look at the astonishing number of music venues active in Woodstock, and what makes its scene so special.
Levon Helm Studios
160 Plochmann Ln.
Instead of trolling Woodstock Festival-seeking tourists with an empty lot, we’d direct them to Levon Helm Studios, where the legend of the town’s folk, blues and rock scene lives on in its most authentic incarnation. This is as close to Woodstock ‘69 you’ll get in ‘22.
The story of Bob Dylan, The Band, and their manager Albert Grossman is long and colorful, and best told through the many books chronicling their history together here in the Hudson Valley.
The story of Levon Helm Studios began six years after the festival, when it was designed by the eponymous drummer for The Band and raised in 1975. But a fire destroyed, and it wasn’t until it was rebuilt and into the 2000s that mounting medical bills from throat cancer treatment pushed Helm to open the doors to the public for his “Midnight Ramble,” a tradition of all-star performances that continues to this day, even after Helm’s death in 2012. In fact, the next Ramble takes place this New Year’s Eve.
Levon Helm Studios is a very intimate venue, with seating for just over 100 audience members, with more packed in standing room only areas. It’s beautifully crafted and unique, with a state-of-the-art sound system juxtaposed against the woodsy, rustic atmosphere one would expect of Helm’s musical home.
Ticket prices can reach into the triple-digits, but once you take a look at who’s been on past bills, it makes sense. Previous performers include Mavis Staples, Emmylou Harris, David Crosby, Jackson Browne, Elvis Costello, and other music royalty, as well as more modern acts of repute like My Morning Jacket, The Black Crowes, and Mumford & Sons.
Standing shoulder-to-shoulder with the area’s most dedicated music fans, viewing a stage where so many larger-than-life artists have showcased their craft, it’s easy to see by the look on the musicians’ faces that playing Levon Helm Studios is just as fun for them as the listening audience. It’s a truly magical venue that does graceful justice to Woodstock’s roots.
Bearsville Theater
291 Tinker St.
Bearsville Theater, originally created by Bob Dylan’s manager, Albert Grossman, has gone through several incarnations over the years. In 2019, Willow resident Lizzie Vann bought the theater and its surrounding complex of buildings, quickly setting out to revive the venue into the best version of itself. The space was renovated and ready to come back to life, with attention-grabbing decor paying tribute to the most legendary icons of the Woodstock music scene. Then the pandemic hit. Ouch.
What goes up must come down, and as the pandemic waned, Bearsville Theater slowly emerged from its cocoon, finally able to display its vibrant colors and character. The walls are once again reverberating with music, and the venue will host one of the hottest New Year’s Eve parties in the county this year.
The venue itself is incredibly unique, with a wrap-around reception bar/lounge that overlooks the stage through a large window. Inside, there’s a small balcony and a big floor for seating or dancing. The lighting and sound systems are fully immersive. Audience members feel very close to the performers. There’s also an outdoor area to relax in, perhaps enjoying a tasty local beverage or snack in the warmer months. We’re excited to see what 2023 — could this be Bearsville’s biggest comeback in its long history of comebacks?
Colony Woodstock
22 Rock City Rd.
Colony routinely draws impressive crowds, booking an incredibly diverse range of acts including popular local bands, fun tribute shows, and big names in independent music. Acts from the area relish the chance to play a real-deal music venue, while touring artists are often pleasantly surprised by the warm and enthusiastic welcome Woodstock’s audience provides.
Like the aforementioned venues, Colony boasts unique architecture. Its high ceilings and wrap-around balcony overlook a large open floor facing a small, almost cabaret-style stage. The expertly executed sound and lighting create an intimate environment conducive to unforgettable, high-energy performances.
With the tribute scene exploding as of late, this venue is the premiere spot in the Hudson Valley to unironically ride a wave of music nostalgia. Though there’s nothing at all wrong with taking music seriously, sometimes concerts are about having fun above all else. And besides its cover bands, Colony books some of the most high-energy, big-fun local and national acts around. This electrifying venue has consistently evolved to become one of the town’s most exciting hubs of sonic activity.
Maverick Concert Hall
120 Maverick Rd.
In 1916, if you asked about the “Woodstock music festival”, you would have been directed to the then-newly-built Maverick Concert Hall.
Hervey White was progenitor of the area’s arts colonies, a man whom some historians call “the first hippie”. After helping found the Byrdcliffe scene, he led the construction of this truly one-of-a-kind indoor-outdoor music venue, built by volunteers from heavy timber and wide planks of wood. The venue is with an otherworldly mosaic of diagonal windows, cocooned in organic splendor, surrounded by lush woods. And as it turned out, the concert hall’s acoustics turned out to be breathtakingly spectacular.
The Maverick is known nationally and even internationally for hosting the longest-running summer chamber music festival in America. The highest-caliber musicians of the classical scene still jump at a class to play for a small audience in a room that has history, charm and aural satisfaction in equal abundance. It was also where John Cage’s most famous and profound work, 4’33” (which features nothing but silence) was premiered, confounding the audience with an act truly befitting of the “Maverick” venue name.
Thanks to a shift towards hosting more diverse genres and acts beyond its fame as a classical ensemble mecca, the Maverick is energizing yet another new generation of music fansentranced by the magic of an acoustically stunning, over century-old venue in the middle of the woods. Their 2023 season is highly anticipated.
Byrdcliffe Theater
380 Upper Byrdcliffe Rd.
The Woodstock art colony that started it all, Byrdcliffe was founded as a creative utopia in the woods at the turn of the last century. Its theater still stands, and still hosts a fiercely independent and experimental cast of characters.
Byrdcliffe was the more well-heeled counterpart to the often anarchic Maverick Artist Colony. Through the dedicated work of the Woodstock Byrdcliffe Guild, it continues to support artistic endeavors that search to find deeper meaning during a modern age of technological distraction.
Set atop a mountain, surrounded by towering trees, the Byrdcliffe Theater’s main room can fit around 100 guests. Windows behind the stage peer into the forest, and a balcony at the back of the hall overlooks the warm, barn-like atmosphere of the interior —just in case you thought Woodstock had enough rustic, one-of-a-kind, historic venues.
Though music comprises but a fraction of Byrdcliffe’s programming, we recommend catching a show when you can. The humbling hand of history feels upon your shoulder in this ancient church of the arts.
Woodstock Playhouse
103 Mill Hill Rd.
The Woodstock Playhouse is where The Band recorded Stage Fright with Todd Rundgren in 1970. Fearing a repeat of the mob that swamped the Bethel-area festival, the Woodstock town council vetoed the idea of allowing a live audience to be present, so the recording progressed out of sight from screaming fans. Who could blame them? They had earned their “I told you so” rights after the down disallowed the original festival from taking place there.
Today, the Playhouse is a cornerstone of the community, hosting orchestras, rock school performances, musicals, plays, jazz bands, and everything in between.
It was built over 48 days in 1938, and changed hands several times but always featured some form of concerts, plays, and musicals. It was a long-standing hub of cultural activity until succumbing to a fire in 1988. This legend would not die though, and in 2011 it was fully brought back to glory, going on to host some of the area’s biggest theatrical and musical performances, including local luminaries and national names.
The legacy of the Woodstock Playhouse is one among many echoes of the town’s legacy as an arts and culture center. Even an all-consuming fire cannot keep Woodstock’s culture down.
Pearl Moon
52 Mill Hill Rd.
Pearl Moon regularly hosts a range of solo artists and other acts (many local) on its small yet sophisticated stage. The ambience of this family-run restaurant/bar/music venue is classy yet rustic, a perfectly Woodstock vibe.
Locals and tourists alike have taken to Pearl Moon’s delicious menu and generously-poured cocktails, and the dreamy yet polished atmosphere is truly mesmerizing. Top-notch sound and lighting further the entrancing environment, separated into three areas: A front main floor with bar astride, a middle seating area, and a rear, pink room that feels very VIP.
Even as one of the area’s newest offerings, Pearl Moon is dripping with Woodstock character. It’s a place where the food and drink doesn’t take a backseat to the entertainment — it’s one big multisensory ride-along where indulgence is encouraged.
Station Bar & Curio
101 Tinker St.
Station Bar & Curio is always a good time, and you can find everything from singer/songwriters giving intimate performances to DJs spinning 45s, to full bands rocking out at top volume for a hard-partying audience.
The building was built by the Ulster & Delaware Railroad Company in 1900, originating in Brown’s Station, a village that was flooded to make way for the Ashokan Reservoir. After moving to Ashokan, it was finally laid permanently in Woodstock in 1970, sitting abandoned, unaware of its destiny as a live music and party hotspot.
This is another venue that embraces the wide musical flavor profile, but unlike the more done-up stages around town, this one feels more like a house party. The sound and lighting are still great, but the vibe is decidedly more laid-back and let-loose.
Catskill Mountain Pizza
51 Mill Hill Rd.
In “the bar room” of Catskill Mountain Pizza, you’ll find a hidden gem of a music scene. The acts are often bluegrass, jazz, country or folk duos or trios, and singer/songwriters… perfect acoustic performances for this exclusive haunt. The pizza is great and the beer selection is superb, so definitely don’t miss an opportunity to drop in and enjoy a uniquely Woodstock experience.
The Pines
5327 Rte. 212, Mount Tremper
A touch outside of Woodstock city limits lies a lodge and restaurant (no reservations) that harkens back to a time when the Catskill Mountains reverbered with a half dozen backwater booze-and-music joints. Though infrequent, musical performances here are often similar in style to Catskill Mountain Pizza, true “music from the mountains”.
Join the family! 
