“After 15 years of running coffee shops & consulting we decided we wanted the fun and freedom of hitting the road, sharing a great coffee experience wherever we go. We’re a family-owned & operated coffee catering company based on Muheconneok land in the southern Berkshires.”
— Best Damn Espresso website
“We’re pretty private people. So coming up here and getting super involved wasn’t the expectation. We came to the Berkshires to relax and enjoy a different lifestyle,” Asio Highsmith admits. “But this coffee truck situation kicked our life into a whole other gear.”
Asio and Angela Highsmith have been together for 23 years, living in Brooklyn most of that time. Best Damn Espresso is the culmination of what they’ve launched together over the years. “We know how to execute an idea and understand customer service and branding, so we know we can do this at a high level,” Asio says. “When we decided on this idea, we went all in.”
To understand how they decided on this idea, it helps to know that they owned a coffee shop in Brooklyn (WTF, opened in 2009), a sneaker store next door, and a local cocktail bar down the street (from roughly 2004 to 2016). Hence, this isn’t their first “high test” adventure. “That was a completely different era in Brooklyn,” Asio explains. “We saw gaps in the culture of the neighborhood that could be filled with good things, and we filled them.”
Asio and Angela had extensive modeling/acting/hospitality careers prior to starting their businesses. “It was amazing,” they are quick to acknowledge, offering opportunities to travel to incredible places and take their young family along.
Angela, a nature lover and trained herbalist, recalls coming up from the city every weekend as a family, camping and renting summer houses. “We started going to Woodstock and Hudson beginning in 2010 and kept gradually heading east,” she explains. They made it to the Berkshires (Harlemville) in 2015 and eventually moved here full-time in 2021.
The Hawthorne Valley Waldorf School, where their children attended summer camp and community events, was an anchor for a long time. “As we kept exploring further east, we found the communities more aligned with our lifestyle and family values,” Angela says. The family eventually settled outside Great Barrington.
A genius idea is born—and hits the road
“I wasn’t really interested in getting back into coffee unless I owned the building,” Asio states. “But my wife had a genius idea. She said, ‘You should take all of our old equipment [which was sitting in their basement at the time] and put it on a truck.’” They decided it was worth a shot.
“We’d seen the coffee business for long enough that the whole vision landed pretty quickly and easily in different forms,” Asio continues. Being a bartender for many years, he was also a master mixologist and was used to working in a tight space. “I don’t need much,” he smiles. They currently have a coffee fleet consisting of a “big truck,” a tiny trailer (“about as small as it gets, with just enough room for two people”), and a small cart for catering indoor events.
“It doesn’t take much to be effective,” he maintains. “In my opinion, it’s about providing great customer service, having a professional attitude, and believing in what you’re presenting. You have to know your stuff and maintain a comfortable setting.” The couple holds themselves to high standards on both counts, working hard to live up to their superlative name and create a communal, loving environment. “Getting something that’s worth the money and worth the wait is important. It doesn’t matter if it’s bartending or baristing. It’s all the same thing,” Asio states.
While their acting and modeling backgrounds help when dealing with customers, as Angela points out, “We don’t put too much mind to our entertainment selves up here. We still have agents and work from time to time, but we came here to hear our own voices, be expressive, and have something else going on besides the constant desire to land the next role.” Like many Berkshire-based artists, they find it refreshing when people are oblivious to their past and enjoy the different way of life this area nurtures.
Keeping a lane open for possibilities
To find out where they’ll be on any given morning, all you have to do is text ‘BDE’ to 844-659-1203. Most Saturdays, the truck is parked at Farnsworth Cannabis (123 Main Street, Great Barrington), and most Sundays, it’s at the Mill River General Store (New Marlborough). But don’t expect to see a rigid schedule. “We want to be mobile and have maximum flexibility while still having a system to reach our customers,” Angela says.
Most of their locations have evolved through partnering with other business owners, including Peter Chapin and Maddie Austin at the Mill River General Store and Chapin Fish at the Monterey General Store. “We typically have a host that introduces us to the community, putting us in touch with the inner neighborhood so we have good cross-promotion,” Asio explains.
“Peter and Maddie put the word out to their customers, and the business continued to grow. I like to think we’ve helped create a more vibrant community in each place we park,” he adds.
Local artist Margaret Buchte’s recent oil painting, “Morning Coffee”—placed in the Mill River General Store’s front window—proves his claim. Per Buchte’s website, “Many people gather and chat while they wait to get coffee, and afterward, they enter the store.”
The Highsmith’s current circuit extends north to Stockbridge, Lenox, and Pittsfield, south to Millerton, and west to Columbia County, where they will pour their coffee at the Copake Farmers’ Market in a few weeks. “Now that we have a permit, we can spread out more,” Asio says. “We’re resistant to being locked in anywhere,” Angela adds. “We still consider ourselves in the research phase of the business where we want to try things out before we commit. We want to keep growing in an organic, community-minded way.”
“We live here, too, so we’re definitely aware of the community-building aspect of this area, and we want these symbiotic relationships to grow,” Asio explains. They’ve done movie sets, festivals, and other public events, as well as private weddings and catering. Many of those gigs happen on the weekend. “We’re mobile and still want to have fun and do beautiful and great things. It’s a real dance, but it’s what we signed up for. We never again want to be in one place every day,” he stresses. (That would be a grind.)
Their sweet spot? “It’s nice seeing how appreciative people are. That really feeds us,” Angela responds. “We’ve crafted a universe of our own creation, and we’re absolutely still growing.”
Their favorite stop? “That would have to be Mill River,” she admits. The bikers, the hikers, the mix of different people from different places, the fact that they live down the road, the way it’s both off the beaten path and The Path… “It’s like a secret gem.”
“I make great drinks, and I love doing it. My wife loves it, too, and we’re doing it for one person at a time. We’re incorporating this business into our lifestyle, and we’re making the best of it, damn it,” Asio says, smiling. “If there’s another opportunity, we’ll take it. We’re big believers in keeping it loose.”
So, whether you’re looking for a traditional espresso with a shot of maple, a matcha latte, a Cafe de Miel, or a refreshing summer Mango Sunrise or Blueberry Milk, there’s a truck around the corner waiting to serve you.
And if you are hosting a gathering, they’re eager to help you serve your guests, too! Check out their Get Caffeinated, Coffee & Treats, and Let’s Hang Out options on the BDE website for two-, three-, and four-hour stints with full barista service.
