Defining the urban winery,
right here in Worcester

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Defining the urban winery, right here in Worcester

TASTING ROOM

EVENTS

Come visit us in the iconic Higgins Armory Building!

100 Barber Avenue, in Worcester!

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

TEMPORARY HOURS:

Due to the ongoing COVID-19 (Coronavirus) situation we are only selling wine bottles to-go, curbside wine service, and home delivery by appointment.

We are readily available however to deliver wine to your home (without contact) and to meet you at the winery for bottle purchases, including curbside. Simply email orders@sailtotrail.com or send a text to (774) 243-2048 and we’ll gladly work with you to set something up that is convenient.

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WHAT PEOPLE ARE SAYING

Sail to Trail WineWorks

5.0

Based on 25 reviews

Laura H

21:16 29 Feb 20

Great little wine tasting room in Worcester, try it! Would recommend they sell cheese and crackers here, you can bring... your own but we didn't know that before stopping in on a whim.read more

Kimberly Rogers

20:09 22 Feb 20

This place is a hidden gem and I'm so glad Worcester is its home. I had the wine flight and enjoyed all five of the... wines, which is a rarity as far as wine flights go. The Zinfandel is the best. And Missa, the Sommelier is very knowledge and friendly!read more

Jaime Loach

17:09 22 Feb 20

I really enjoyed my time at Sail to Trail. Missa taught me all I needed to know about their wine offerings and helped... my make an educated decision about my purchase. The wine was DELICIOUS!!!!! I had two glasses there, which Missa poured and chilled for me. When it was time to leave, she packaged up my (OPENED) wine bottle in a sealed bag to take home. I highly recommend!read more

Chris Vasiliadis

20:29 19 Feb 20

Attended a private networking event here last night - what a unique, fun space! It was neat to have the opportunity to... have a single glass of wine or opt to purchase the whole bottle and take home whatever you didn't finish. Great small business to support!read more

Lisa McKenna

00:05 08 Feb 20

ABSOLUTELY AMAZING!! The wines are by far the best in town..The Red Zinfindel is deliciously fruit forward...So so... good!! I will be definitely going back.read more

Michael Clark

22:41 21 Jan 20

We stopped in early on a Friday to check it out. Already hopping at 5pm. The owner Chris greeted us cheerfully at the... door (as we observed with all customers, even though we like to think we're special). The one thing that really stood out is the quality of the wines across all varietals. Typically you find a wine where you say, "I didn't like that one" ... not the case here. I'm typically a red wine person, but I enjoyed the whites just as well. Great view of the Worcester city scape and a comfortable place to unwind for a bit.read more

Kristin McDonald

22:31 18 Jan 20

Couldn’t be more happy!!! Finally found a red I’m in love with. Waited for friends at a table while they were... running late the winery staff couldn’t be more fine with it even with the fact they were filling up. New favorite spot in the cityread more

Eleanor Gilmore

20:27 11 Jan 20

Love supporting another locally-owned business! Great wine portfolio; friendly, informative staff.

Kathleen Sharr

01:50 03 Jan 20

This is such a wonderful addition to Worcester! Love coming here. This place is da bomb 💣!

Andrea Borge

21:29 20 Dec 19

Excellent wine and very personable wine maker! Worth the trip for sure.

Debra Mooney

18:39 20 Dec 19

A fantastic and appropriate reuse of an iconic Worcester The wines are amazing and Chris is lots of fun to talk to.... Definitely add to your must-see in the Woo.read more

Emory Payne

23:26 30 Nov 19

Best winery on the east coast!!! Tasted just like Napa 🍷🍷🍷

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

20:29 30 Nov 19

Wonderful find! The staff was so friendly and welcoming. Will definitely go back!

Liz Codd

19:51 19 Oct 19

Delicious, high quality wines and friendly staff!

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

Next Reviews

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 enjoying a curated selection of kickass wines sounds like your bag, come on by and visit us in our chill Tasting Lounge, check out our current offerings online that can be delivered right to your door, or join our wine club.

Sail To Trail In The News

Eight Massachusetts products with awesome labels I couldn’t resist Instagramming in 2019

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Sail to Trail WineWorks Appoints Missa Capozzo as Sommelier and Executive Vice President of Product Development.

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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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