November 4, 2026 from 5:30-8:30 p.m. in historic downtown Frederick, MD.

Whether you are a seasoned connoisseur or a curious newcomer to the world of American whiskey, this evening promises a curated balance of bold spirits and artisanal flavors.

• Heaven Hill, in addition to their namesake, this is home to spirits like Larceny, Old Fitzgerald, Elijah Craig, and Rittenhouse
• Penelope Bourbon, a relative newcomer to the scene, this bourbon maker finishes wheated, toasted and limited-release expression from an Indiana distillery
• Jefferson's Bourbon, known for the uniquely aged-at-sea "Ocean" small batch blend, they've been breaking boundaries and unlocking new possibilities since 1997

​The culinary team at Wye Oak Tavern has designed a bespoke menu to complement the specific tasting notes of each pour. Moving beyond standard pub fare, these pairings are engineered to highlight the caramel, oak, and spice found in the glass.

Start with a light cocktail and mingle with friends before settling in for the full experience. You'll be served bourbon and whiskey tastings alongside scrumptous food that highlight each flight.

The evening will end with a fast and rowdy game of Rockhouse Roulette, where you can win one-of-a-kind items (or try to "steal" someone elses).

A portion of the proceeds benefit the Frederick County Career and Technology Center's Student Construction Trades Foundation, helping the next generation of craftsmen get a quality education.