Jen Milano found the perfect formula for being a successful entrepreneur while also maintaining a family life.
“What started as an idea turned into the most rewarding experience of my life,” said Trumbull resident Milano, owner of a boutique, full-service, mobile bartending company called The Vintage Horse. “It started during the global pandemic when I was furloughed from my 13-year career in the hotel industry while on maternity leave with my daughter (and) with an 18-month-old son at home. I was looking for something to call my own while bringing in an income for our family.”
Now, with a busy family life, she’s a successful female entrepreneur, building a company that offers her flexibility and a sense of purpose.
“This journey has been rewarding for me and allowed me to grow personally and professionally. I was able to be more present with young kids these last 5 years while making an impact and doing something I love,” she said.
Established in 2021, The Vintage Horse hosted 55 events in its first six months.
“We’ve been growing ever since,” Milano said. “What started as a creative solution to a problem I experienced has become a business dedicated to helping people enjoy life’s most memorable moments. Staying visible, building relationships, and consistently delivering great events has been the key to our success.”
A fully functional bar is housed inside a restored horse trailer that also serves as a statement piece to provide a unique bar experience. It serves a variety of customized craft cocktails, beer, wine, and specialty beverages, with menus for each season. “A big trend we’re seeing is the rise of mocktails and non-alcoholic options,” she added. “Guests want beverages that are just as fun and flavorful as cocktails, so we’ve expanded our menu to include creative mocktails and wellness-inspired drinks.”
Also, Milano creates signatures drinks, personalized menus, and custom signage to complement a customer’s theme, style, and décor. “We’re seeing clients become more budget conscious. By allowing clients to provide their own alcohol, we help them save significantly compared to traditional venue bar packages while still delivering a high-end bar experience.”
Rina Bakalar, Trumbull’s director of economic and community development, remembers when the business was first established.
“I thought it was a great concept,” Bakalar said. “Vintage Horse brings a unique venue to Trumbull and Connecticut, helping to make an event special and memorable. I’m excited to see them five years later still in business and growing. We love to see folks living locally opening businesses and expanding their businesses in Trumbull and statewide, in this case.”
After Milano had a mobile dessert truck at her wedding in 2016, she appreciated the experience it offered for guests and soon discovered mobile bars built from trucks, campers, and horse trailers, and started envisioning her own. She found her first trailer on Facebook Marketplace in Redding.
“While the idea of converting a horse trailer into a mobile bar seemed exciting to me, many people thought I was crazy,” said Milano, said Milano, who worked with a mobile bar business coach. “When I reached out to builders and welders for help, I was either told, ‘We don’t do that.’ There were many moments when I considered giving up because I couldn’t find anyone who understood my vision.”
She explained how she came up with the name for her business.
“The name Vintage Horse comes from two of Milano’s interests. I’ve always loved anything vintage, and I wanted the brand to capture that timeless charm and elegance. I also grew up riding horses, so when I decided to renovate a horse trailer into a mobile bar, incorporating that piece of my story into the business name felt like the perfect fit,” she said. “My family and I did much of the work ourselves, and I vividly remember painting the inside of the trailer the night before our very first event.”
Milano acknowledges entrepreneurship is challenging.
“Success requires persistence, adaptability, and the ability to stay positive even during difficult moments. I’ve always had the mindset that I can accomplish anything I set my mind to,” she explained. “I’m fortunate to be surrounded by strong, inspiring women who encourage, motivate, and support one another.”
Her 13-year career in hospitality also helped her develop resilience and confidence. Bartending during college also inspired her. “I loved the energy, interaction, and excitement that came with being behind the bar. Combining those experiences felt like a natural fit,” she said.
Although starting as a one-woman operation, The Vintage Horse has grown exponentially. Now, Milano now has a team of six female bartenders.
“Each member of our team is trained, certified, and experienced in serving events of all sizes, from intimate gatherings to large weddings and corporate functions,” Milano said. “They continuously bring fresh ideas, creative cocktail concepts, and innovative ways to improve the guest experience and event efficiency.”
In addition, the business includes two horse trailer mobile bars, two white portable bars for indoor and outdoor events, and a champagne wall experience. Milano even has her own mobile bar coaching program.
“My main goal is showing other female entrepreneurs that they are capable of anything, and their vision has no limit,” she said. “My vision has always been to create a business that allows me to be both a present mom and a successful entrepreneur.”
