Defining the Urban Winery in Worcester, Massachusetts

The Sail to Trail tasting room is a gathering spot where everyone knows your name. Kind of like your local PTA meeting, except it’s in Worcester and the uncomfortable awkwardness  has been replaced with a living room. We keep the ambiance simple — no fancy white tablecloths, stately mahogany furniture or intimidating wine speak, mainly because we don’t know any.  Better to get in touch with the aromas you smell, the flavors you detect and the sensations you experience during our intimate- yet not too intimate- fantastic wine voyage.

Sail To Trail is the The first winery to call Worcester home

Our Wines
The Club

Come Hang Out With Us

Sail To Trail Tasting Room
100 Barber Avenue, Worcester, MA

By Appointment only (for now).

Our tasting room is a place to seriously get into wine without getting too serious. Sip your wine. Listen to our music. Sip your wine a little more. Enjoy old fashioned conversation. And if all goes well, refuse to leave without buying a few bottles to share with your mate by the fire pit, serve at a dinner party or take to a celebration.

Sail To Trail In The News

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…

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

But life sometimes takes different turns,

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Craft beer seems to be all the rage, with dozens of new breweries opening every year in Massachusetts. Chris Simpson hopes to change that story by opening a winery in the Higgins Armory in Worcester.

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Sail to Trail Wineworks Worcester Massachusetts Winery

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