THE OPPORTUNITY
By investing in Sail to Trail WineWorks, you will support a business that is defining the urban wine experience in New England.
- Proven Demand - We’ve already identified a loyal customer base in Worcester, Massachusetts through our initial launch in the historic Higgins Armory.
- Competitive Advantage - We are the only urban winery in the area that has created a unique tasting room experience while providing an excellent portfolio of bottled wine.
Overview
Sail to Trail is an urban winery located in Worcester, Massachusetts. With additional capital, we will expand into a new location since we are outgrowing our current location and expanding the types of wines that we offer.
Sail to Trail WineWorks is the premier urban winery in New England, where vineyard vibes get an industrial edge. Goodbye wine country, hello wine city.
You might be wondering whats an urban winery. Think a brewery but instead of beer, we are serving great wine. Its not all about geeking out over wine, we are building a community and having fun doing it.
Just because Sail to Trail doesn’t have all the trappings of high-end wine culture doesn’t mean its tastes aren’t high-end.
Wine comes from grapes. And great grapes are great grapes. Whether from East Blue Ball or Napa Valley, Sail to Trail considers them equal. Why? Because some of the best wines come from the places you may have never heard of. Sail to Trail filters out the crappy ones and gets the best ones directly to you.
Each of our limited-edition wines is the product of extensive research and time spent traveling the country to find the very best grapes—without bias, preconceived notions or old-school wine snobbery.
A Good Grape is a Good Grape: A Note FROM THE FOUNDER
Just because Sail to Trail doesn’t have all the trappings of high-end wine culture doesn’t mean its tastes aren’t high-end.
Wine comes from grapes. And great grapes are great grapes. Whether from East Blue Ball or Napa Valley, Sail to Trail considers them equal. Why? Because some of the best wines come from the places you may have never heard of. Sail to Tail filters out the crappy ones and gets the best ones directly to you.
Welcome to the brave new world of wine.
—Christopher Simpson
Offerings
- Tasting Room Experience
- Bottled Wine
- Wine Subscription
- Online Sales / Wine Delivery
Our Story
In 2018, Chris noticed an untapped market - the urban winery. We have all seen wineries out in the country but why can't we have a great wine tasting experience in the city? The name refers to Worcester’s unique geography allowing residents to hit the beach and the slopes all in one day.
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.’”
In the press
