Long before European settlers arrived in the Connecticut River Valley, Native Americans gathered beneath the massive branches of the Charter Oak — a sacred tree that became one of the most enduring symbols of American independence. Nick Melillo grew up in that same valley, surrounded by the fields and farms where some of the world’s finest wrapper tobacco is grown. The Charter Oak line is his love letter home — to Connecticut, to its tobacco heritage, and to the man who first put a cigar in his hands.

His grandfather worked the line at Winchester Repeating Arms after returning from World War II, earning a modest living but never missing his daily Connecticut Broadleaf. That ritual — that quiet devotion to a good cigar — is woven into every Charter Oak that leaves the factory. Available in three distinct expressions, the Charter Oak gives every smoker a place to land, from the silky smoothness of the CT Shade to the bold earthiness of the CT Broadleaf.

Why You’ll Love It

A Valley’s Worth of Heritage: The Connecticut River Valley has been producing world-class wrapper tobacco for centuries — the Charter Oak puts that legacy front and center with every draw.

Three Expressions, One Story: The CT Shade, CT Broadleaf, and Habano each tell a different chapter of the same Connecticut story — smooth and creamy, bold and earthy, or perfectly balanced between the two.

Critically Acclaimed Value: The Charter Oak Habano earned Cigar Aficionado’s #1 Best Value Cigar award — proof that honoring tradition doesn’t have to break the bank.