The owners of Happylife Productions bought the former Tinker Street Cafe at 59 Tinker St. from local entrepreneur Lizzie Vann for $999,000, securing a long-term future for their Woodstock-based arts and culture store after several years as tenants.
Artist Mike DuBois and his wife and partner, artist Kelly Sinclair, said their lease was nearing its end, raising the possibility that a new owner might force them out. Vann bought the building, below Bob Dylan’s former apartment, from the Center for Photography at Woodstock in 2021 for about $1 million.
“I was not going out of my way to buy this building,” DuBois said. “Lizzie was putting it on the market and gave us the right of first refusal. We don’t have that kind of money.”
Founded by DuBois, Happylife Productions is known for its mix of vintage and contemporary photography, visionary and pop-surrealist art, music-inspired merchandise, and psychedelic collectibles and jewelry. The shop produces much of its own work, including clothing, prints, stickers, magnets, and notecards.
It sells artwork and imagery tied to musicians in Woodstock’s countercultural past and present, including Dylan, Levon Helm, Holly Scanlan, the Grateful Dead, Amanda Rasmussen, Jimi Hendrix, and Olive Parisi-Brannock. DuBois has been creating concert posters and merchandise since the 1980s, including official work for the Dead, Phish, Black Sabbath, Fleetwood Mac, Goose and the Allman Brothers.
“I’m one of the tentacles of these cultural entities,” he said, noting his collaborations with Bearsville Theater, Levon Helm Studios, and other arts institutions. “They’re wonderful anchors of culture in Woodstock.”
The 225-year-old building, later known as Café Espresso and then the Tinker Street Cafe, has hosted the likes of Ozzy Osbourne and the Dave Matthews Band. DuBois created logos and graphics at the Tinker Street Cafe during its heyday between 1988 and 1999.
Starting in the 1920s, it was known as the Nook, a popular local gathering spot. Café Espresso opened in 1962 and quickly became a magnet for musicians. Dylan wrote portions of Another Side of Bob Dylan upstairs in what was dubbed “the White Room,” now The Overlook’s newsroom.
Café Espresso hosted jam sessions and performances by figures such as Hendrix, Joan Baez and Ramblin’ Jack Elliott. Tinker Street Cafe, opened in 1988 under co-owner Jerry Mitnick and Freddie Sandel, and became a late-night gathering spot for musicians living or recording in Woodstock. It hosted impromptu performances by everyone from Rick Danko to John Sebastian, Gregg Allman, Joey Ramone, the Dave Matthews Band, and members of R.E.M.
Besides Happylife and The Overlook, the building’s tenants these days include Queen of Rogues, an arts space dedicated to theater, music, film and dance, and Peace, Love & Cupcakes.
Vann said she decided to sell the two-story building to ensure that longtime cultural stewards remain in place—and also to free up money for her next mission, Project Regeneration, her proposed redevelopment of several properties surrounding the former Woodstock Library, which she estimated could cost about $10 million. A vote on amending zoning laws to allow the project to move forward is set for as early as Feb. 17, according to Town Supervisor Anula Courtis.
That instinct—keeping Woodstock’s cultural ecosystem intact—was echoed by Peter Shapiro, the concert promoter who oversees programming at the Bearsville Theater.
“We like existing people and stewards of the vibe getting to stay in Woodstock for a long time,” Shapiro said. “I plan to be at the Bearsville Theater for a long time.”
The Happylife sale comes about three weeks after Vann listed Bearsville Center, the historic complex that includes the Bearsville Theater, for $7,995,000.
“This is about recycling the money,” Vann said. “Project Regeneration is going to be expensive.”
Vann said she undertook preservation and structural repairs to the Tinker Street building in recent months in anticipation of a sale. That work included a full reconstruction of the building’s front porch roof.
Turning the property over to DuBois and Sinclair felt natural, she said.
“I’m a friend of Happylife,” Vann said. “We’re both big Dylan fans.”
Noah Eckstein is the editor-in-chief of The Overlook. Send correspondence to noah@theoverlooknews.com.
