If you’ve ever found yourself walking along Tinker Street trying to figure out why Woodstock is called “the most famous small town in America,” the Woodstock Rock Tour might be for you.
The tour begins where it all started, at Café Espresso. Opened by Bernard and Mary Lou Paturel in 1960, the Espresso might’ve remained a local French bistro, but something interesting was happening just up the road.
“Albert Grossman had just moved up to Bearsville,” explains tour guide Larry Germack, referring to Bob Dylan’s larger-than-life manager. “Dylan followed Grossman, and everyone else followed Dylan.”
Germack leads you up the Espresso’s back stairs to the “White Room.” It was here that Dylan, who’d befriended the Paturels, penned such classics as “It Ain’t Me Babe” among others. The room features a recreation of Dylan’s writing desk, complete with ashtray full of cigarette butts, nice touch.
Between Greenwich Village folkies circulating through the Espresso and the bigger acts signing with Grossman up the road, this tiny upstate town was suddenly on the world’s music map in a very big way.
As the tour continues along Tinker Street, the stories are not necessarily site-specific, but since the village looks much as it did fifty years ago, tales of Hendrix, Van Morrison, Janice Joplin and others who walked its streets just sort of fall into place.
Corresponding photos are regularly produced from Germack’s shoulder bag, illustrating such moments as when the whole town showed up on the Green to welcome Muddy Waters.
Germack, who goes by the name “Pittsburgh Larry” even though he left the Steel City decades ago, is a gifted story teller. Some tales come from folks he’s met, others can be found in books like Barney Hoskyns’ Small Town Talk, an absolute must-read for anyone interested in Woodstock’s music history.
The tour includes some local history that’s essential for context, particularly how the tradition of Bohemian festivals in Woodstock dates way back to the 1920s at the Maverick Colony.
A visit to the Woodstock Cemetery, where both Levon Helm and Rick Danko are buried, is of course a springboard for many stories about The Band, photographer Elliot Landy, and the like.
A short drive (in your own car) then extends the tour to Bearsville Center, originally created by Albert Grossman and recently renovated by Lizzie Vann. While touring Bearsville Theater, Larry continues to talk about Grossman, plus Todd Rundgren, John Sebastian and others.
The photography at the theater dovetails nicely with the tour, much like the displays back at the Espresso, which Lizzie also recently brought back to life.
“I think Larry and I are on the same page,” Lizzie says. “We share notes regularly about the new discoveries we make. Woodstock is such a wonderful repository of art and music history, and we both love it with a passion.”
The tour includes the theater’s Green Room, which has been completely reimagined as a sort of Buddhist chill-out lounge, celebrating the spiritual side of Woodstock.
From Patti Smith to REM to the Rolling Stones, the list of artists who recorded in Bearsville is impressive. When you add this to other artists like Bowie and the B-52s who recorded elsewhere in Woodstock, it’s almost staggering.
When a woman taking the tour asks how all these famous musicians didn’t get swamped by admirers, Larry explains that the locals were pretty reserved for the most part.
“When the stars came out to play, it was a supplement to the real action behind closed doors,” he says. “When the going got rough in town, they’d get into their cars, smack into a guard rail, and go home.”
(Note: driving while impaired was more common in Woodstock at the time than texting-while-driving is today.)
While getting to visit some of those tucked-away places might be interesting, it’s a logistical challenge this tour does not attempt to tackle. For this you will have to use your imagination along with the handy map in Hoskyns’ book.
At the tour’s conclusion, all the folks who’ve taken it seem quite satisfied. Some have come from as far as Ireland, and most enjoyed other related attractions while they were here.
“I was in town for the Midnight Ramble at Levon Helm Studios,” says Zac Casperson, a school teacher from Ohio, who also ate at the Bear Cantina and did some shopping on Tinker Street.
For locals who’ve been here since back in the day, maybe a two and a half hour tour can’t measure up to their personal memories of Woodstock’s rock heyday, but plenty of others will find much to appreciate on the tour, whether you’re visiting or live nearby.
Things like the Rock Tour and a revived Café Espresso are great ways to remind folks that it’s not just the name of the festival but what actually happened right here that makes Woodstock the most famous small town in America.
The Woodstock Rock Tour runs April through October, Saturdays at 2pm and Sundays at 11am. Tickets are $44 and can be booked online at rockjunket.com/activities/woodstock-music-tour.
Join the family! 
