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    Chesapeake Trading Company

    4.0 (16 reviews)

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    5 days 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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    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.

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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.

    Guilford & Company - Guilford & Company, St. Michaels, MD -- beautiful decor at holiday time!

    Guilford & Company

    4.4(10 reviews)
    0.0 mi
    $$$

    I had been searching far and wide for a ring for my wife for Christmas. Most stores had the same…read moreold thing, but Guilford & Company, aside from their knowledgeable and friendly staff, had a wide selection of styles and price ranges. I found a great ring at a fair price that I am sure will thrill my wife this Christmas. I'm sure I will shop there again, and they have free parking behind the store, which is a huge plus in St. Michaels.

    Having ogled some gold estate/signed pieces in the window over the past couple of days, I finally…read moredragged my husband in for an impromptu first visit..... I wasn't expecting much, but, WOW. It turns out that the good stuff is hidden in the store. Case after case of antique diamond and gemstone jewelry! We may need to visit Guilford and Co. every time I'm in town! I was surprised at how large this store is. The pieces are displayed well, grouped by era as well as stone type, as far as I could tell. I also couldn't believe how many Edwardian and Art Deco pieces they had on site. I mostly browsed the gemstone rings, but I'd imagine that this would also be a great place to purchase a piece with dreamy old cut diamonds! They also have a GIA GG on-site who is available to answer more detailed questions. Some standouts -- -a warm L/M round cut diamond in a glowing emerald halo with absolutely GORGEOUS tiny milgrain detail on the bezel -an intricate and HUGE Art Deco diamond brooch/pendant that I didn't dare try on -a high carat yellow gold ring set w/ a rich, dark amethyst cab -a fireball of an orange sapphire set in a halo ring -a blue moonstone ring set in an angular diamond and filigree halo -several Edwardian diamond rings in the central case, including what looked like a three-stone of old (mine?) cut diamonds in a filigree setting -and.... Well, I could go on and on, but I don't imagine anyone is actually still reading this. :) I should also mention that it is a very comfortable, low pressure environment to browse in. The SA was more than happy to dart from case to case, and even suggested different items for me to try on. She was friendly, informed, and very easy to get along with -- No fake nicety or condescension here. I actually told her directly that I'd used up all my "spending points" on jewelry this month, but she just kindly asked what I'd used them on and then continued letting me try on the pretties. Can't wait to make a return visit. I'm already (secretly, shhh) plotting another trip to St. Michaels.

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    Guilford & Company
    Guilford & Company
    Guilford & Company - Tiffany & Company Diamond (3.5ct.) and 18k Yellow Gold pin, 12.4dwt

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    Tiffany & Company Diamond (3.5ct.) and 18k Yellow Gold pin, 12.4dwt

    Chesapeake Trading Company - womenscloth - Updated September 2026

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