How one of Osheaga’s founders revamped an Eastern Townships dive bar

For those in Montreal’s live music industry, Dan Webster hardly needs an introduction.

Known as one of the co-founders of Osheaga and founding Greenland Productions in 1993, Webster has been a concert promoter in Montreal for several decades now. Now, he’s trying his hand at a very different kind of endeavour in the business of live music.

During a drive along the Bolton Pass in the Eastern Townships in late summer 2020, Webster and wife Carrie Haber discovered that a long-standing local watering hole, the Thirsty Boot, was up for sale. Their connection to the Boot runs deep, as Haber’s uncle came up with the bar’s name.

Situated in West Bolton near the popular tourist town of Knowlton (about a 90-minute drive from Montreal), the Thirsty Boot has long been a staple among drinking establishments in the area. The couple had been out in that area earlier in the pandemic, as they’d set up wifi at their cabin in Sutton so they could work there remotely.

“We drove by and thought, ‘Oh, you know, victim of the pandemic, that’s the way it goes,’” he says. “A few weeks later, we went by again — I think it was a particularly sunny afternoon in the autumn — and the second time we looked at it, it grew on us and we got a little more curious.”

Some time after that, Webster noticed the bar’s then-owner sitting on the bar’s balcony, and decided to go inside and take a look. Even though the place looked run down, he was “immediately charmed” by the Thirsty Boot and saw potential in it as a space for live shows. Coming back the next day with Haber and her cousin to meet some of the locals, all Webster had left was to decide if the Boot was worth investing in.

“It was a risk during COVID, with a lot of other people running away screaming from things like bars and events venues,” he says. “I started to think that there was a silver lining in it, and something that could be done — and that I might have the time over the period with all the shows that were cancelled to put some work into it and fix it up.”

While the Boot has only been operating since 1962, the building itself is around 150 years old. This meant that a facelift was needed for the bar in its 60th year — renovating the stage, building a back deck overlooking a lake, revamping the bar’s food offerings (their summer menu offers fare like tacos, burgers and salads), and replacing windows and other worn-down parts of the building. 

The Boot’s interior is wooden with timber beams and a resonator—already making for great acoustics in that room. In terms of the events and shows one would see there, the offerings are diverse: concerts (from disco to jazz to country), small festivals (indoors and outdoors), family get-togethers, and film screenings. 

So far, the Thirsty Boot has booked artists like AHI, Shane Murphy, Li’l Andy, Blue Coupe (consisting of former members of Alice Cooper and Blue Öyster Cult),and Montreal alt-country-folk supergroup El Coyote. In September, Jake Clemons — the saxophonist for Bruce Springsteen and the E Street Band — will be stopping by for his own show.

Montreal indie favourites Plants and Animals will also be playing there in the fall. Though Webster says they’re still building connections with artists, the events the Boot has put on to date have been very well-received, and he’s noticed people driving there from out of town to attend certain shows — 10 to 25% of them from the Montreal area, as well.

The Boot’s initial heyday was arguably from the ‘60s to the ‘80s, when the Mont Glen ski hill was open, before traffic at the bar started declining during the 2000s. Despite the lack of both customers and upkeep in those years, he’s confident that they’ve rebounded from that.

“I think we’re back to the pre-doldrum phase,” he adds. “We’re busy every weekend. We reopened the kitchen, which was a big thing. Now, there’s a lot of people coming for the kitchen in the afternoon to sit on the back deck. There’s people coming in for the shows. Then there’s the old regulars coming in and out. I can’t say an exact increase in numbers, but it’s definitely growing again.”

From the outside, the Thirsty Boot is worlds apart from the hustle and bustle of Parc Jean-Drapeau during Osheaga weekend, as the festival attracts tens of thousands of people annually. But it wasn’t always quite that massive. Webster, who The New York Times described in 2005 as “something of a godfather to [Montreal’s] alternative rock scene,” remembers Osheaga’s early days as being run by a small group of people “wearing many, many hats” with smaller-sized crowds and a relative lack of infrastructure. For example, he says co-founder Nick Farkas was shovelling and evening dirt to prevent concertgoers from slipping in the mud.

“What we’re doing with our little eventual festival site [at the Thirsty Boot] is not very different from what we were doing at the beginning of Osheaga,” he continues. 

“We built the community piece by piece and made connections. Now, those events are colossal at Parc Jean-Drapeau. There’s a huge team, and the spending is probably going up minimum 10 or 20-fold. But the concept of bringing it all together in the beginning is really similar to what we’re doing at the Thirsty Boot.” 

The Boot also has plans to host artist residencies, where they’d “live” at the venue earlier in the week before performing on a Thursday or Friday. Since a multitrack recording studio is set up in the bar, those artists can also use it to do pre-production for their tour, or record music after their tour. Webster says they plan on doing these residencies from winter 2022 to early 2023, while also offering more festival events next summer.

With all of this in mind as Montreal’s festival season continues, Webster offers some enticing reasons why festival attendees from out of town should stop by the Thirsty Boot on their way to or from Montreal. 

“They need to see some of the beauty of Quebec outside of Montreal, to get away from the air pollution and heat islands that we have in the cities,” he says. 

“Between the mountains and the flowing streams and the fields, it’s just a different environment. It feels fantastic. The food is good, the local produce is good. There’s a huge arts scene. It’s a nice break from the city.” ■

For more on the Thirsty Boot, please visit the establishment’s website.

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