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Sperry Products

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Our Story

Located in beautiful downtown Saint Michaels, Maryland, Chesapeake Bay Outfitters has been outfitting its patrons’ “Shore Style” for over thirty years. At Chesapeake Bay Outfitters, we pride ourselves in providing stylish and classic women’s and men’s clothing, footwear, and accessories, with an understated resort vibe.

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Cashmere Galore

Women's Shoes

Featured Products

Women's
Tops

Men's
Shoes

Men's
Tops

Women's
Accessories

Mens's
Accessories

Mens's
Swimwear

Men’s Sperry Billfish – The Icon

Sturdy and rugged, this three-eye boat shoe features enhanced shock – absorbing soles the true workhorse of the fleet.

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"About this time the custom arose of referring to the Eastern Shore with capital letters, as if it were a special place; this tribute was never paid the western shore."

― James A. Michener, Chesapeake