Love Our WInes? Check Out The LADDER 7 WINE CLUB!


A Note From Our Founder:

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.

Truth be told, I stumbled upon this business idea years ago as a former engineer while interviewing for a position at a company that manufactures submarine parts (of all things). I was prepping for my interview with their CEO, and while researching, I found that he served on the Board of Advisors at a wine company. I was trying to understand how the hell subs and wine ended up on the same guy’s resume, but soon became fascinated by the industry at large. 

I’ve always had an entrepreneurial spirit, and spent the next year focused on research and planning. Next thing I knew, I was walking away from the 9 to 5 grind and bottling a kick-ass Cabernet Sauvignon. Now, in partnership with an amazing team of dedicated wine experts, I am thrilled to bring my vision to life and share my findings with you.

The Ladder 7 Club reflects the tremendous pride and respect that I have for my Grandfather. He was a firefighter here in the City of Worcester Fire Department, Ladder 7, out of the old Winslow Street Station for 35 years. Prior to, he volunteered to serve in the United States Army during World War II. About as personal as branding gets, am I right?

Thank you for joining me on this journey! Nothing brings me more joy than hearing from our customers, so please reach out with any and all feedback (or drop us a line to say hello!).


Chris Simpson
Sail to Trail WineWorks