Sail To Trail WineWorks
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Sail To Trail WineWorks
The first and only winery in the uber-hot city of Worcester MA. Bringing you the wine varietals you love (no raspberry wines here) with a chill brewery vibe. After all.who said great wine needs to be bougie? We offer free wine delivery*, curbside pickup, and are the coolest wine hangout this side of the Mississippi River.
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Welcome to Sail to Trail WineWorks, I'm so glad you're here! For background, our name was chosen to celebrate New England's diverse physical geography, honoring the place I'm proud to call home-Worcester, MA. In one day, residents and visitors can sail up the coast, hike a mountain, and still have time to kick back and relax with a glass of wine.
New England's hottest new winery is bringing you outstanding examples of every wine varietal that we bottle, right to your doorstep. We have a membership that will suit every budget, plus, club members are eligible to receive exclusive offers and discounts that are available only to club members!

In honor of our Founder's grandfather, who fought fires in Worcester on Ladder 7 for 35 years, $7 from every 6-Alarm or Let-It-Burn shipment will be donated to the WFD Box 4 Special Services truck, that provides invaluable on-scene services to first responders.
We're casual here at Sail to Trail Wine Works. We just draw the line at a frosted glass of wine. You won't find ice cubes here, but we do have those fancy whiskey stones that'll do the same thing. This date symbolizes putting Argentina on the world's wine map. Malbec, Aregentina's flagship grape. Few things stir up so much controversy and drive so many decisions as a mere number or grade on a bottle of wine.
Use our space and drink our wine-relax with friends, family, coworkers, business partners or anybody you'd like! For $200/hour* plus the cost of wine, you'll have use of our entire tasting room. You'll be able to customize the mood to make your party just right! Choose the music you'd like to help set the tone, and use our two retractable banners and large television for visual displays or presentations to complete the mood.
Reviews (15)
Greendale Hub
Greendale Hub
Jan 16, 2022
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Unbelievable the service provided. I am typically a low sugar red wine lover ONLY. The Chardonnay was beyond expectation and Cabs were so well done. Wish we could have stayed all night, I think they would have let us. Felt welcome and educated. Thank you Sail to Trail for the amazing experience.
Chris R.
Chris R.
Jan 02, 2022
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This review is so overdue. We have been here multiple times and love it! The building is so unique and cool. When we walk into Sail to Trail it's like walking into the loft from the show Friends. Couches, a hammock, and a long family style table in addition to regular high top tables and a small bar offer multiple seating choices. The wine is excellent which pairs nicely with the light food offerings. The owner is amazing!! So welcoming and knowledgeable. Everytime we have gone here all of the guests are having a blast. If you have not tried it, you should make a trip you will not be disappointed
Sarah Comeau
Sarah Comeau
Dec 19, 2021
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I had so much fun it’s a great environment and the wine is delicious! The atmosphere is easy and everyone is friendly!
Krista Backiel
Krista Backiel
Oct 18, 2021
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This place was such a wonderful experience! Went with a group of 6 ladies last night and we all loved it. Very cool building and neat space they have. The owner was extremely hospitable and knows his stuff. The wines were really good and they have great little snacks to pair with them. Highly recommend the chocolates, they were delish. A little off the beaten path, but worth the excursion. It almost has a bit of a speakeasy feel, very cool.
Weenie Fred
Weenie Fred
Sep 30, 2021
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One of the most magical locations for enjoying a sunset in all of Worcester. Not to mention the exquisite wine, artwork, music, company, and general atmosphere. Come for a glass of wine - stay for a game of chess - leave with a sense of community. I cannot recommend Sail to Trail enough.
Sami C.
Sami C.
Sep 23, 2021
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Wine flight and complimentary Cheezits :) You can bring your own food as well. Perfect place to go on a rainy day
Kimberly Nobrega
Kimberly Nobrega
Sep 20, 2021
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Tell us you ❤️ hanging out at @sailtotrail without telling us you ❤️ to hang out at Sail to Trail Winery 🍷
We had a blast enjoying a wine tasting of all their delicious offerings paired with decadent chocolates from @therapychocolate , another local business based in Framingham, MA. 🍫
We 💖 supporting local, small businesses because we 💖 putting money back into our community. Worcester’s only urban winery is located in the Woo’s famous Higgins Armory Building and operates Wednesdays through Sundays.
To learn more about hours, their story and visiting the Tasting Room give
Katherine B.
Katherine B.
Sep 13, 2021
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I loved coming here with my friends! The wine they have available is fantastic and the service was truly unbelievable. Everyone was so nice, and I would love to come back here again.
Marilyn Perez
Marilyn Perez
Sep 13, 2021
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An awesome time. The bartender Stacey is the best! I will come back for sure!! Just so inviting!!
Ron Cheli
Ron Cheli
Sep 12, 2021
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One of the best wine bars I have been to in years. Bar staff is happy and friendly and always willing to help out. If you’re looking for a great wine and a unique spot definitely stop in.
Rich Penta
Rich Penta
Jul 17, 2021
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Went here with my wife and one of our friends to catch up and it was an amazing time. Erin was amazing it was almost like she was one of our friends who just happened to be working there. She’s very knowledgeable and really enhanced the overall great time we had there. We had a ton of laughs and enjoyed the wine, chex mix and got to play Clue and Uno. What more do you need? Highly recommend it if you are looking for a new winery to visit.
Amy B.
Amy B.
Jun 19, 2021
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I lived in Worcester on and off as a child and my family decided to make a day of visiting the city. After enjoying a Coney Island dog and saying a drive by 'Hi!' to Turtle Boy, we headed over to Sail to Trail, located in the former Higgins Armory.

The location evokes memories of school field trips and medieval knights. The actual tasting room uses the space well - it is not huge but comfortable without being crowded. The mural is everything Worcester - love it!

Being beer drinkers, my husband and I had the red sangria - possibly the best sangria I'd ever had with nice notes
Jeremy D.
Jeremy D.
Apr 21, 2021
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Had an awesome time here with my wife and some friends back in March. Chris, the Founder, was super nice and knowledgeable.

The location
Unique spot in the old Higgins Armory in Worcester. I grew up right near there and haven't been in the area for quite a while. The space is well decorated and the view out the windows was nice with the sun setting.

The wines
Fantastic. Tried a flight and then doubled down on the Malbec. Boom. Took a few bottles home as well. Apparently this was a newer wine and it was killer. The rest of the flight was good too, Cab Sav was my second favorite.

The
Samantha M.
Samantha M.
Oct 19, 2020
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This place is the perfect hidden spot for some delicious wines. If you're looking for an "Instagram" worthy place, this is the spot. One of the employees, Chris, was not only helpful and very intelligent on wine, he was very personable, and made the whole experience worth it. If you get the chance to go, make sure you pair your wine flights with the truffles they offer. Each truffle corresponds to the wine you are drinking. This will be the spot I take and show all of my friends who are down to drink some wine. Not only is the wine and staff amazing, but they even have games you
Daniel B.
Daniel B.
Aug 02, 2020
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Great wine and greater place . a must stop by on Worcester. The owner is a great guy.