EXPERIENCE

Experience Chesapeake

Our Lounge

Step inside Chesapeake’s lounge, where fascinating characters, spirited debates, exceptional tobacco, and unexpected friendships create an atmosphere that’s unmistakably ours. Come for the smoke. Stay for the experience.

Tuesday Club

History, hearty laughter, spirited debate, and unforgettable characters await! Join the Ancient & Honorable Tuesday Club of Annapolis, which meets every Tuesday at 6:30 pm, where a tradition dating to 1745 is still making history.

Pipe Night

At Chesapeake, Pipe Night is more than a gathering. It’s where newcomers become regulars, strangers become friends, and our shared passion for exceptional pipes and tobaccos brings everyone together.

Events & Memories

From legendary gatherings to unexpected adventures, Chesapeake creates experiences worth remembering. Explore what’s coming next, relive the laughter and camaraderie, and discover why our best stories are shared.

Tastings & Discoveries

With 450+ pipe tobaccos, exceptional cigars, and passionate experts, Chesapeake invites you to venture beyond the familiar, discover hidden treasures, and experience the thrill of finding something extraordinary.

Classes & Masterclasses

Ever wondered what separates a good smoke from an extraordinary one? Join Chesapeake’s tobacco experts for hands-on discoveries, fascinating insights, and masterclasses that transform curiosity into genuine expertise.

Voices Of Chesapeake

Don’t just take our word for it! Discover what our customers say about Chesapeake’s extraordinary tobacco, welcoming community, genuine hospitality, and the experiences that keep them coming back.