Rachel Shuster

Sail to Trail WineWorks is Worcester’s first boutique winery offering the city’s wine drinkers something new and tasty.

Founder and CEO, Chris Simpson, a Worcester native, is excited to bring this fresh take on a winery to the city. His goal is to simplify the wine conversation in the industry and create a community of customers who feel comfortable and open to be a part of that conversation.

Sail to Trail wines began with Simpson’s experience in the corporate world as an engineer, with the consistent dream of starting his own business. “I spent a long time in the corporate space,” Simpson said. “I realized that if I wanted to start my own business, it was now or never. One day, I was interviewing at a company on the South Shore and I was going to interview with CEO. I looked at his LinkedIn profile and saw that he was on the board of directors at a winery.” With his interest peaked, Simpson went on to check out that winery and on the website, there was information about the industry and it was then that it clicked. “I started to realize that this was an industry that I could get into,” Simpson says. “This industry is new for this area. The thought of bringing in varietals that are in demand to Worcester…I just kept peeling back the layers and thought, ‘I could do this. The city would love it and it’s the right time.’”

Flash forward a year and a half later, Simpson explains how he got to this point after that fateful day where it all clicked. “We have been exploring relationships with vineyards for a year and a half, working with sommeliers, brokers, etc.,” Simpson says. “We reached out to vineyards and asked what wines they have and what wines meet the criteria of our clientele. We narrowed down 100 wines to five which we have now that provide wine at a great value.”

Sail to Trail is unique in that the focus is on providing customers with carefully crafted, limited edition varietals that are in demand. “We want to be on leading edge of things that are becoming more popular, for example, unoaked Chardonnay,” Simpson adds. “The quality of wine, subtleties in flavor…the things that are on the leading edge in terms of what consumers are looking for in their wine.”

Sail to Trail offers five labels in four varietals – Sauvignon Blanc ($20), Chardonnay ($20), Zinfandel ($35), and two Cabernet Sauvignons – a premium ($18) and a reserve ($40). Something else unique? The company’s name. “Growing up around here, I was raised to believe that our geography is something special,” Simpson says. “In this area, we can be on a beach and on top of a mountain all in the same day, which the name suggests.”

The biggest reward for Simpson thus far? “When I take wines to restaurants and tell the people about them, I can see on people’s faces, ‘Oh wine from Worcester…this is going to be lousy,’ Simpson says. “Then I give them a sample, and I love literally being able to watch their faces and see that they think my wine is really, really great. Their eyes light up.” On the flip side, navigating the legal and regulatory system has been a tough, eye-opening, and new journey for Simpson, however, it’s all been worth it to see how much people love his wines.

Sail to Trail does ship their wines to customer doors, but they also have a tasting room in the Higgins Armory building. “We have everything in place to do tastings and sell out of here,” Simpson adds.
At the end of the day, Simpson’s love for the city is at the root of why he brought Sail to Trail to Worcester. “More than anything, I could have set up shop anywhere, but I wanted to be here, because I love this city,” he says. “I am proud to bring this to the city of Worcester.”

For more information, visit sailtotrail.com. Cheers!