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    Chesapeake Trading Company

    4.0 (16 reviews)

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    4 days ago

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    2 years ago

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    2 years ago

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    5 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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    4 years ago

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    8 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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    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.

    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 September 2026

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