Premium Cigars

Discover our carefully selected collection of Premium Cigars

Fine Tobacco Pipes

Explore traditional craftsmanship and exceptional pipes

Pipe Tobaccos

We have more than 450 tinned and bulk selections for every palate

Accessories & Essentials

The tools and accessories that complete your smoking experience

Welcome To Chesapeake Pipe & Cigar

Award Winning & Expertly Curated

Discover an extraordinary selection of hand-rolled premium cigars, masterfully crafted tobacco pipes, expertly blended pipe tobaccos, and thoughtfully curated accessories. From our meticulously maintained humidor to our knowledgeable, personalized service, every detail reflects our passion for quality, craftsmanship, and tradition. Whether you're a seasoned connoisseur or just beginning your journey, we're here to make every experience exceptional.

Discover Chesapeake

Our store, our people, and the products that make us special.

Experience Chesapeake

Great company, shared traditions, and moments worth remembering, including Tuesday Club, Pipe Night and other special gatherings.

Explore At Chesapeake

Exploring the knowledge, history, and craftsmanship behind the smoke though our ever growing library of articles and videos.

Shop At Chesapeake

Visit Our Brick & Mortar Shop In Annapolis Maryland Or Shop With Us Online