Sail to Trail: Forging New Trails as Worcester’s First Winery

While being first to market can have its benefits, it also means forging new paths, and in the wine industry, this can be a regulatory challenge—and that was pre-Covid. Chris Simpson’s winery, Sail to Trail, the first in Worcester, MA, had only been open for five months when the shutdown of March 2020 hit. As a new business, not to mention an entirely new concept for the area, Chris had to think fast.

“Not only was Sail to Trail a new concept for the community, but my goal was always to take the brand nationally,” said Simpson. “Covid. while throwing a few wrinkles in our local plans, also gave us the opportunity to shift toward retail and direct to consumer expansion.”

But how did this all come about—a winery in an old mill city outside of Boston? Chris wasn’t in the wine industry and grew up mostly on beer—as did the local community. Worcester, however, was changing. Recognizing the need to make a significant shift to keep jobs and residents from leaving for outside opportunities, the community actively began to attract biotech and medical research companies. With the 11 colleges and universities, including a teaching hospital in New England’s second-largest city, it was a natural fit. Today, Worcester is a thriving college town – even named the new “it” town by NPR in 2018.

Around this same time, Chris was prepping for an interview in his previous field – aerospace defense engineering. He came across a line in the CEO’s bio that caught his eye. His interviewer was on the board of a winery. As a wine drinker and aspiring entrepreneur, his wheels began to turn. What if he opened a winery here in his hometown? Was it possible? Breweries were opening left and right, but no one had yet applied that concept to wine, and there was certainly a growing appetite for wine in the community. And so, recognizing it was now or never, Chris set out to open the city’s first winery under the old Burgundian négociant model.

Négociants are merchants who buy grapes, juice, or finished wine from growers, then bottle and sell it wholesale on the market. This model is in place today worldwide and includes well-known wineries such as Louis Jadot, known for selling some of the finest wines on the market. The goal of a négociant is simple, to take on the expenses of bottling and marketing the wines while the farmers focus on growing grapes.

“I began researching the regulations, getting the paperwork and licensures in order, while also sourcing wine experts, growers and winemakers on the West Coast to work with,” said Simpson. “I knew the buying trends for wine in the area and what my friends were drinking, and I wanted to provide a local option for enjoying the wines we all love.”

By October 2019, Chris opened Sail to Trail, Worcester’s first winery and one of the state’s first urban wineries. He began with five varietal wines—two Cabernet Sauvignons, a Chardonnay, Sauvignon Blanc, and a Zinfandel—each carefully crafted and offered as limited editions. The wines were offered via e-commerce nationwide as well as in the hip but laidback tasting room within a former armory building.

“You don’t see vineyards from our windows, but what you do get is distinctly Worcester and entirely approachable,” said Simpson. “It’s a welcoming place where neighbors fast become family. It’s a place to kick back, enjoy good wines without any kind of pretension and have a good time.”

Prior to March 2020, Sail to Trail was enjoying 25 percent week over week sales growth. Word of mouth was bringing in new customers, and the community was embracing its first winery. Then, as was the case for restaurants and wineries across the country, everything came to a screeching halt with the newly instituted Covid shutdowns. Fortunately, for Sail to Trail, in securing his permits, Chris lucked into the ability to offer delivery, which became a lifeline from March through June for the business.

“Our customers were great! They’d call and order their favorites, and as long as they were within the 25-mile radius, I was throwing boxes in my car and making deliveries,” Simpson said.

Knowing this wasn’t going to sustain the business forever, Chris also began to step up his retail presence growing from eight retail positions to placement in 52 locations across Massachusetts and New Hampshire. He has plans to further his distribution to neighboring states, including Rhode Island, Connecticut, and Vermont this year, while putting wheels in motion for a greater national presence to come.

“Sail to Trail is a lifestyle brand. Here in Worcester, we can go from the boats to the trails all in an afternoon,” said Simpson. “It’s about accessibility, approachability, and simply chilling with friends and having a dang good time. I’d like to bring that to wine drinkers everywhere – great wine at reasonable prices with a local heart. Like a good friend, we’re a brand you can count on to come through.”

Sail to Trail wines currently retail between $20 to $40. And with the Zinfandel already selling out, Chris has already added two new limited varietals to his offerings, including a Petit Verdot and Malbec. Additionally, he and his small team of sommeliers, an educator, and a marketer have aggressive expansion plans in the coming years. Sail to Trail has begun to seek distributors across the country with plans to expand in retail outlets nationwide and is currently working on a second-tier line of wines that will retail below the current offerings.

“Through our e-commerce offerings, we see the brand resonate across the country,” said Simpson. “I’d love to amplify that growth through distribution of our existing line, but also of wines at the $10 to $12 price point, which we hope to position in both retail and entertainment venues. My goal is to surprise our customers with the quality of wines offered for the price.”

Sail to Trail is also looking into canned wines as part of this second-tier line-up.

“I realize it may be a challenge to take a Massachusetts wine nationwide, but I strongly believe in five years, it will be a well-known brand,” said Simpson. “Being first in the market is a challenge we’re conquering, and we’re changing perceptions on the way, and I think it all comes back to that local mentality – a neighborly brand that you can count on to come through.”

Sail to Trail’s Worcester tasting room is once again open, at limited occupancy levels, for tastings, flights, glasses, and bottles. The wines are also available to ship through the winery’s e-commerce site and can be found in restaurants and stores within New England.

“Although not the start we had planned, this past year has taught us to embrace change, think bigger, and work smarter,” said Simpson. “I’m sure we won’t be the only urban winery in the region for long, but there is something special about being the first. And we are grateful to our community for embracing us.”