1. Chesapeake Trading Company

    1. Chesapeake Trading Company

    0

    Saint Michaels, MD

    Chesapeake Trading Company

    3.9 (15 reviews)

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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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    Review Highlights - Chesapeake Trading Company

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

    Mentioned in 3 reviews

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    Chesapeake Bay Outfitters

    Chesapeake Bay Outfitters

    2.5(8 reviews)
    0.0 mi
    $$

    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.

    Jutta deserves ten stars!! She was so helpful today. I had questions about a dress I really liked…read morebut wasn't sure it could be altered. She was extremely knowledgeable and very kind. I also liked that she asked if she could touch the clothing while I was wearing it (underneath my arms) to show how it could be sewn. I really "lucked out" with the 50% off sale today. Ugg flip flops were even 1/2 off. Unfortunately, most of the shoes I really like were full price. Oh and their pashmina dress toppers. Dreamy....

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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

    The Preppy Redneck

    The Preppy Redneck

    3.8(8 reviews)
    0.1 mi

    I love this store and the kindness and interest Courtney takes with every single potential…read morecustomer. This is typically the store I visit first. So much "shorely" you'll find some unique items for kids and adults of all ages. Thank you!!

    Bottom Line: One of the best stores in Saint Michael's filled with gifts, decor, toys, books and…read moresuch. I have no idea what a preppy redneck is but I know I like this store. There are lots of gifty stores on the main drag, N. Talbot Street, in Saint Michael's but I think this is one of the best! I particularly enjoyed looking at the kids section including the various stuffed animals, toys and games. I couldn't help myself from flipping through some of the Priscilla Cummings books as I remember when she visited my school as a kid. I've been a fan of Chadwick the Crab ever since! I also liked looking at the various products from the J.O. Spice Company. I come from a family of commercial crabbers and this might come as a shock to some but JO, not Old Bay, is our preferred crab seasoning. But J.O. isn't just for crabs and they offer spice blends and other stuff like chicken rubs, crab cake mixes and steamed shrimp seasoning. Aside from the above, I also enjoyed looking at cards, soaps, Scout bags, novelty salt and pepper shakers and such. The employee, perhaps the owner, was friendly and welcoming as most people are in this quaint town nestled along side the Miles River. This was definitely a fun stop!

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    The Preppy Redneck
    The Preppy Redneck
    The Preppy Redneck

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    Chesapeake Trading Company - womenscloth - Updated July 2026

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