the urban winery,
at your doorstep


Shop Our Wines
Join The Club

the urban winery, at your doorstep


Shop Our Wines
Join The Club

Starting Thursday, October 10th

Join us for a FREE wine tasting at the Higgins Armory Building 

Thursday | 12:00pm – 8:00pm

Friday | 12:00pm – 9:00pm

Saturday | 12:00pm – 6:00pm

Sunday | 12:00pm – 4:00pm

Now shipping to Massachusetts!

So first things first…Here at Sail to Trail, we love wine. And we’re dedicated to bringing great wines, at great value, to you. We’re so sure that you’ll love our wines, that if you aren’t completely happy with your purchase, we’re telling you right now that we’ll make it right. Period. Bottle was leaking? No problem. We’ll send you another one if you want or give you your money back. Ditto if we send the wrong bottle (Super unlikely, but hey…we’re humans here at Sail to Trail. And heck, it might turn out to be your new favorite!). Long story short, if you aren’t completely thrilled with us or our wines, we’ll figure out a way to make it cool. Pinky swear. So why the hell wouldn’t you give our wines a try?

And with that…

Sail to Trail WineWorks is the premier urban winery headquartered in New England, redefining the stereotypical “cork-dork”. No snooty somm-speak (we don’t know any anyway). No questioning anyone’s opinion of what makes a great wine. No need for Alexa to chime in on your next purchase. NOBODY has time for that. 

Thanks to our industrial roots and vineyard vibes, we’re bringing edge and inclusion to wine by ditching the snobbery and doing the work FOR you to ensure we’re bottling and curating kick-ass wines from across the globe. 

We think a great grape’s a great grape. Whether it’s raised in Blue Ball Delaware, Funk Nevada or Buttzville New Jersey, we don’t discriminate. That being said, most grapes don’t end up in our bottles – Hey, not everyone gets a trophy. But, when we do uncover the over-achievers, we bring them to the table to enjoy at your leisure.

What sets us apart you might ask? Every bottle of wine that we bring to you is a limited edition that has been carefully crafted and curated by members of our incredibly talented team. That means it’s uncommon for our members to try the same wine twice (Note to self: order your favorites in bulk!). Long story short: You’re getting exclusive selections with every order.

So cheers to top notch wine without the B.S—delivered straight to your doorstep! Just click, ship, sip!

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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…

Read The Article

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

But life sometimes takes different turns,

Read The Article

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.

Read The Article

click. ship. sip.

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