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Come visit us in the iconic Higgins Armory Building!

Thursday | 3:00pm – 9:00pm 
Friday | 12:00pm – 9:00pm
Saturday | 12:00pm – 6:00pm
Sunday | 12:00pm – 4:00pm

Find Sail to Trail wines at these fine establishments:


Sail to Trail WineWorks is the premier urban winery in New England, where vineyard vibes get an industrial edge.

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.

So, if getting a curated selection of kickass wines delivered right to your door sounds good to you, check out our current offerings or join our wine club.

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Sail To Trail In The News

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

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Chris Simpson’s urban winery Sail to Trail opened in the Higgins Armory Building last week. Simpson works with a sommelier to personally select each wine that carries his label.

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Sail to Trail WineWorks has opened a tasting room in Worcester’s former John W. Higgins Armory building, offering a location for customers to sample and purchase bottles.

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Sail to Trail WineWorks has as its goal to offer refreshing, inclusive experiences to every lover of wine, not just those who wax poetic about legs, tannic structure or notes of red fruit compote.

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Emory Payne
Emory Payne
23:26 30 Nov 19
Best winery on the east coast!!! Tasted just like Napa 🍷🍷🍷
Katherine Rafuse
Katherine Rafuse
20:31 30 Nov 19
A wine diamond in the rough! Had a great time here. The wine was great, especially the Zin. Super friendly and knowledgeable staff. Can’t wait to come back!read more
Amy Auclair
Amy Auclair
20:29 30 Nov 19
Wonderful find! The staff was so friendly and welcoming. Will definitely go back!
Liz Codd
Liz Codd
19:51 19 Oct 19
Delicious, high quality wines and friendly staff!
B King
B King
22:25 13 Oct 19
Sail to Trail WineWorks is a great place to try some great wines and learn about all that Sail to Trail has to offer. Just minutes from the heart of the city Sail to Trail offers a relaxed atmosphere for people to taste test and purchase their favorite products. You'll definitely want to ask Chris what his favorite wine is currently, you won't be disappointed!read more
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