The first urban winery in New England to be bottling in-demand varietals, from the finest grape growing regions in the world.

Sail to Trail WineWorks partners with vineyards around the world to develop, blend, and bottle amazing wines produced from grape varietals that would typically be difficult to impossible to grow in the northeastern United States.

Sail to Trail believes that a great grape is a great grape…whether it’s raised in Blue Ball Delaware, Funk Nevada or Buttzville New Jersey.

A designation only achieved if aspiring grapes pass our exhaustive background check:

Are they fit grapes?
✓ Are they happy grapes?
✓Are they educated grapes?
✓ Are they void of prestigious BS?

Unfortunately, most grapes don’t end up on our wine menu – hey, not everyone can get a trophy. But that’s good for you because if America is a melting pot of world culture, then the Sail to Trail Tasting Room is the eclectic wine barrel of Western Hemisphere Grapes. We team up with the best Cabs, Pinots, Chards, and Zins and introduce them to you in our funky, fun and friendly Worcester tasting room.

Please understand we weren’t always grape fanatics. Truth be told, owner Chris Simpson stumbled on the joys of grapedom while interviewing for a submarine design position. “I discovered the CEO was on the Board of Advisors of a wine company,” he said. “It triggered an unexpected fascination with the world of wine. After researching the various options, I decided to take a leap of local business faith and create the first urban winery in my hometown of Worcester. Being part of its Renaissance feels like the right thing to do.”

He chose the name Sail to Trail to celebrate cozy New England’s diverse physical geography. Chris reasons: “In one day, residents can sail up the coast, climb a mountain, and still have time to relax afterwards in the city with a glass of wine. Preferably, conversing with friends at Sail to Trail’s comfy lounge. More than anything else, I want visitors to feel at home here.”

And he means it.

The Tasting Room Is Coming Soon!

In the historic John Higgins Armory Building
100 Barber Avenue, Worcester, MA
Grand Opening & Tasting Hours TBA

For starters, the Sail To Trail Tasting Room will be a spittoon-free premises. Good lord. We absolutely do not want to remind you of the dentist’s office.

This is an intimate “come on down and hang out” with us experience. A place to seriously get into wine without getting too serious. Sip your wine. Listen to our music. Sip your wine a little more. Enjoy old fashioned conversation. And if all goes well, refuse to leave without buying a few bottles to share with your mate by the fire pit, serve at a dinner party or take to a celebration.

For those of you who are new to the Worcester (pronounced “Wuss-tah”) scene, get ready for a culture-blowing ride through the funkiest, food-iest, fabulous city in Massachusetts. In 2018 alone, 65 new food establishments opened their doors in what the locals affectionately call Wormtown. There’s theater, arts, sports, parks and more. Worcester is also rich in “idiosyncrasies.” Did you know we’re home to a huge inflatable polar bear, the smiley face and seven hills reminiscent of Rome? We’re proud of our gritty past, and invite you to see how we’ve integrated it into the future.  

If you are joining us for an on-line experience, you won’t find any soaring views of vineyards on the web site. Nothing against them.  They just don’t match our historic urban vibe where slices of green space co-exist peacefully with sidewalks and triple-deckers. Got some “soaring digital views,” though, of our wines out and about in the world sent in by devotees like you.

One final promise, Sail to Trail is committed to bringing you an ongoing series of firsts: The first winery to call Worcester, Massachusetts home. The first urban winery in New England to be bottling in-demand varietals, from the finest grape growing regions in the world. With more to come.

Sip, sip HOORAY!

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Sail to Trail Wineworks Worcester Massachusetts Winery

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