When Cassie Wilson quit her 9-5 to pursue a passion for craft beverages, she never imagined her mobile trailer would evolve into Otisville’s newest hotspot for creative coffee and community connections. Yet in the months since opening its doors, Callie’s Coffee Café has become a must-visit destination in Orange County, drawing customers from all over the Hudson Valley.
An Unexpected Journey
Wilson’s journey to becoming a café owner wasn’t what she had envisioned while earning her psychology degree. Her entrepreneurial story began alongside her husband in 2016, when she helped him grow his food truck business. When the pandemic hit in 2020, the food truck industry ground to a halt as festivals and gatherings were canceled.
“His business switched gears toward catering,” Wilson explains. “People were turning their weddings into backyard barbecues, and he mentioned how nice it would be to offer both food and drinks.” This casual observation sparked something in Wilson, who had always enjoyed creating beverages for friends and family. “Whenever I have friends over, I love to make them fun concoctions,” she says. With only one or two mobile bars operating in the area at that time, Wilson saw an opportunity. By late 2021, she had transformed a horse trailer into “Callie’s Cocktails,” offering specialty drinks for weddings and events throughout the Hudson Valley.
The name came from the couple’s English Bulldog, adding a personal touch to the business. “I didn’t want to name it after myself,” Wilson says. “I wanted something meaningful. We don’t have any kids right now, so our dogs are our whole life.”
From Cocktails to Coffee
After a successful first year with the cocktail trailer, Wilson felt the business could become something more and decided to expand into coffee service.
To make this transition work, she took a significant leap of faith. She left her steady job in banking to focus full-time on building her business. Setting up the trailer at High Point Canine Center in Otisville, she began serving the local community—starting with just a handful of customers each day.
“At first, I would have maybe five customers,” Wilson recalls with a laugh. “But I stuck it out, grew on social media, and pushed it out there to people.”
The persistence paid off. Soon, that trickle of curious locals transformed into a steady stream of devoted regulars and coffee enthusiasts willing to travel substantial distances for Wilson’s creative offerings. “I would have people coming from all over the place, driving an hour just to come to the little trailer in Otisville,” she says, still sounding somewhat amazed by the trailer’s success.
Making the Leap
After a year of serving coffee from the trailer, Wilson began contemplating a permanent location. She was initially hesitant, concerned about disrupting the unique experience that had made the trailer so popular.
“I didn’t want to mess up a good thing,” she admits. Her first instinct was to look at spaces in nearby Middletown, but she had what she describes as an “epiphany” while driving through her hometown. “I saw a ‘for lease’ sign in the building where we’re at now,” Wilson says. “I was just like, ‘Let me call, let me see. Let’s just go take a look.'”
What she found was challenging—a space painted in four different colors that needed significant renovation—but Wilson had a vision for what it could become. The timing aligned perfectly with her planned January closure of the trailer due to winter weather, giving her a month to transform the space.
Her husband, already running his own businesses, proved invaluable during the renovation. “Thank God my husband is very handy,” Wilson says. “He was YouTubing plumbing because he’s not a plumber. He was like, ‘This is my first time doing plumbing, but we’ll figure it out.'” Against the odds, they completed the renovation in just one month, opening Callie’s Coffee Café on February 1 of this year.
The Grand Opening and Beyond
Rather than a soft launch, Wilson decided to “just send it,” as her husband suggested. The grand opening was chaotic but successful. “It was crazy,” Wilson remembers. “But overall, it was incredible.”
Three months in, the café has attracted both loyal trailer customers and newcomers. “I’ve gotten a ton of new customers, just people who either heard about the café or are local to the area who just said, ‘Oh, I didn’t know what that trailer did over there,'” Wilson explains, her eyes lighting up. It’s her palpable passion and exuberance that seems to infuse everything at Callie’s—from the creative beverages to the warm atmosphere that makes customers feel instantly at home.
The Callie’s Experience
Today, Callie’s Coffee Café offers a full range of espresso drinks, including lattes, macchiatos, and cappuccinos. Non-coffee options include chai, matcha, teas, refreshers, iced teas, and lemonades—ensuring there’s something for everyone, including the many parents and children who visit from the nearby Otisville School.
The food menu currently features pastries, donuts, danishes, muffins, bagels, occasional egg bites (made by Wilson herself), and yogurt bowls, with plans to expand to lunch options as staffing grows.
What truly sets Callie’s apart are the monthly specialty drinks that Wilson develops each season. April’s Easter-themed menu featured Cadbury Egg, Reese’s, and “bunny marshmallow” flavors, alongside a strawberry shortcake option. The cinnamon roll flavor remains a year-round specialty and Wilson’s personal favorite, along with the seasonal Reese’s creation.
The café’s aesthetics also play a key role in its success. “I’m very into aesthetically pleasing things,” Wilson says. She created an Instagram-worthy space with a dedicated photo backdrop, understanding that social media exposure drives business growth. “People are going to come get their cute little coffee, take a photo, and post it on social media,” she explains. “Then so many people are going to see it and say, ‘Where is that place? I want to go.'”
Beyond serving beverages, Callie’s has become a hub for connection. Through the event side of her business, Wilson has built relationships with numerous other female entrepreneurs in the Hudson Valley. “It’s an amazing community,” she says, describing collaborations with businesses like Endlessly Linked, which offers permanent jewelry. “These people that I just met by doing events, it turned into this little family. We recommend each other to clients. And that’s how all of us can really grow.”
Looking Forward
Despite being open only three months, Wilson is already dreaming of expansion. “I would love to expand to more locations in different areas,” she says, though she acknowledges there are staffing challenges and growing pains to address first. But her entrepreneurial spirit remains strong—she recently spotted a former ice cream shop for sale in Unionville and immediately considered the possibility of a second location. “I sent it to my husband and said, ‘Do we do this?'” Wilson laughs. “He was like, ‘Relax, you’ve been open a month. Let’s take it easy.'”
For now, Wilson takes pride in building a business from scratch that has become a community favorite in such a short time. “It’s almost like this legacy that maybe can go on for a really long time,” she reflects, “something that started from just an idea that I bounced off my husband.” And while the path from psychology major to café owner wasn’t straightforward for Cassie Wilson, the crowds lining up at Callie’s Coffee Café suggest it was the right one.
Callie’s Coffee Café is located at 185 Grange Road, Suite 3 in Otisville. Cafe hours are Tuesday to Friday, 7 a.m. to 2 p.m., and Saturday to Sunday, 8 a.m. to 2 p.m. For more information, visit calliescoffeecafe.square.site or follow @calliescocktailscoffee on Instagram.
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