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    Chesapeake Trading Company

    4.0 (16 reviews)

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    5 days ago

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    2 years ago

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    2 years ago

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    3 years ago

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    4 years ago

    Love this cute little shop in St. Michaels! I have found several books that I love in this store! There is so much to look at!

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    6 years ago

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    7 years ago

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    14 years ago

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    7 years ago

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    Review Highlights - Chesapeake Trading Company

    Michael's when I went for the first time today.

    Mentioned in 3 reviews

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    Flying Cloud Booksellers

    Flying Cloud Booksellers

    4.4(9 reviews)
    8.0 mi

    A charming shop with a sense of quiet opulence. This is not a small town bookstore in spirit or…read moredesign. The space is beautifully conceived, inviting you to wander slowly and take in every aisle. I genuinely enjoyed the act of browsing here, which feels like a small luxury in itself. The only snag was an assumption on my part. Given the setting, I expected a more robust local history presence or at least a thoughtfully curated selection highlighting the region. Works on Underground Railroad and abolitionist networks, tourism history, or even local ecology felt notably absent. The offerings on Tubman and Douglass were surprisingly thin. Still, the store's elegance and breadth are undeniable, even if its sense of place could be more fully realized.

    I would have happily recommended this bookstore, but my experience last week changed my opinion…read more After purchasing several items, I asked if they could be gift wrapped. The cashier immediately replied, "No." When I asked why, she responded, "Because we're closed." While I understand that it was approximately two minutes past closing time, I was already in the store completing my purchase. A small gesture of customer service would have made a lasting positive impression. Instead, I left feeling that my business was an inconvenience rather than appreciated. Independent bookstores thrive because of the relationships they build with their customers, and I expected a level of courtesy that matched that reputation. I hope the store considers empowering its staff to show a little more flexibility and kindness in situations like this. Great customer service is often remembered long after the purchase itself.

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    Flying Cloud Booksellers
    Flying Cloud Booksellers
    Flying Cloud Booksellers

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    Chesapeake Bay Outfitters

    Chesapeake Bay Outfitters

    2.8(9 reviews)
    0.0 mi
    $$

    I don't enjoy shopping and only do so when I absolutely need something so it was extra special that…read moreI found a winter coat in this summer coastal town. I've always wanted a puffer jacket! Found on a sale rack boasting "25% Off!" the medium men's blue coat was meant to be mine. Roomy and warm for the upcoming winter, stylish and comfortable. What a find! My partner opted for an entire outfit based on sailing. :) Amy was helpful and friendly, helping us find just what we needed and wanted.

    Bottom Line: Large clothing store with nice displays and quality brands…read more Chesapeake Bay Outfitters is a rather large clothing store that offers casual attire for men and women including shoes. They also carry some home décor items. For the most part I eyed up women's clothing and shoes from brands that I often see at Nordstrom like Nic + Zoe, Uggs, Sofft and Olukai. They also had a lot of cashmere sweaters so I spent a fair amount of time perusing the variety. My husband and I also checked out shirts from Chesapeake Bay Outfitters' own line, Rising Tide, which had a terrific feel to them. The store was organized and had great displays. I'm sorry that the reviews for this lovely store aren't better. We didn't have any awful customer service experiences but I will say no one greeted us or acknowledged us which is never good in a retail situation. In most other shops in Saint Michaels the staff were welcoming, friendly and chatty.

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    Chesapeake Bay Outfitters - A view of the storefront.

    A view of the storefront.

    Chesapeake Bay Outfitters - Great Displays. Very Maryland.

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    Great Displays. Very Maryland.

    Chesapeake Trading Company - womenscloth - Updated September 2026

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