Superb Wines.

let me see!
Sail to Trail will bring an outstanding winery experience to the Northeast. We will be providing outstanding wines in great varietals like Cabernet Sauvignon and Chardonnay.


Sail to Trail Tasting Room

100 Barber Avenue, Worcester, MA

By Appointment only (for now).

Get directions

Sail to Trail in the news

  • A great write-up in MassLive this week!

    Christopher Simpson was preparing for a job interview at a top-notch manufacturer of submarine components when a tiny detail piqued his interest — the company’s CEO was also an advisor to a winery in California...
  • Our Interview With the Worcester Business Journal!

    Craft beer seems to be all the rage, with dozens of new breweries opening every year in Massachusetts, with new wineries few and far between.

    Chris Simpson hopes to change that story by opening a winery in a 1,200-square-foot space in the Higgins Armory in Worcester.

  • Our Interview With the Telegram!

    The idea was formulated while Chris Simpson was interviewing for a job designing submarine components.

    But life sometimes takes different turns,