the urban winery,
at your doorstep


Join The Club - get 25% off*
Shop Our Wines

the urban winery, at your doorstep


Shop Our Wines
Join The Club

Join us for FREE wine tastings at the 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:


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!

wines direct winery

Sail To Trail In The News

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.

Read The Article

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.

Read The Article

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.

Read The Article

Sail to Trail Enters a Charitable Partnership with the Worcester Fire Department’s Box 4 Service

Read The Article

click. ship. sip.

Shop Our Wines
Join The Club
sail to trail initial offering
greenwich wine food festival

Follow Us On Instagram


© Sail To Trail Wineworks  |  Contact  |  774.243.2048
Mailing List  |  Terms & Conditions  |  Privacy Policy  |  Credits

Your Cart