We visited some friends in St. Michaels last weekend and did some shopping on Talbot Street,…read moreincluding at Chesapeake Trading Company. It's one of those stores that does its best to defy categorization, but they sell great women's clothing, jewelry, books, home goods, home decor, and more. I was inside for no more than 10 minutes and walked out with a fancy candle, a sweater, and a book. It's a charming shop. I'm sure I'd buy quite a bit here if I lived in St. Michaels. Stop by and check it out!

Some items are pricier than they might be at other stores. The customer service is excellent …read more.. that's worth a lot

Outstanding service. 30-50 Percent off everything in store…read moreas of July 14, 2024. Lu Lu B clothing, unique jewelry and the softest bamboo leggings. It's nicely laid out. I will definitely return in September!!

Excellent shopping experience! I was so happy with the scarf that I purchased and when I told the…read morestaff that it was my birthday, they gave me a pair of earrings! I receive compliments every time I wear them! Highly recommend this shop if you are visiting St. Michael's!

I highly recommend this spot! You can customize various shirts, hats, bags and more. I will say…read morethat the prices are a bit steep but it sounded like the patches are also from a local shop ! The best thing here was the experience. The owners helped me so much and made the whole process very fun!

I visited THE BENCH with family members while I was visiting St Michaels…read more I LOVE the store and MARY, who helped me with my purchase of a shirt. My only regret is that I didn't have more time to spend there. I wish there was a website for me to continue shopping. I will definitely visit THE BENCH again - probably every time I visit ST MICHAEL! Tom/Denver CO

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.

Bottom Line: A historic home full of antiques, vintage-inspired items, home decor, jewelry and…read moremore. My husband I wandered into Sea Captain's Cottage to explore this two-story treasure chest. We enjoyed roaming from room to room between the two floors checking out the eclectic merchandise. Some items were antiques and other were inspired from the past. I'm also perpetually on the hunt for items related to Chesapeake Bay heritage and there was plenty of that at Sea Captain's Cottage. We spent quite a bit of time checking out this delightful store and enjoyed our experience.

Didn't spent much time in this store as it wasn't really our style, but this is basically a mens…read moreand women's clothing store for country folks. ORVIS was a brand they sold here, but they also had a few others that I had not heard of before. Inside you'll find shirts, pants, jackets, sweaters, belts, etc., for both men and women. They also had watches, some luggage items, fishing gear, and decoys. As I said, nothing wrong with the store and the worker here that day was very nice, but style wise, this was not for us.

We reserved a coat to be picked up in 2 days. We offered to pay in advance by credit card. The…read moreowner told us this was not necessary and promised to hold it. We called the day before to make sure it was still there and to offer to pay over the phone. The owner said "no problem". When we got to the store the owner told us he just sold it because a "good customer came in, wanted it, and paid cash". Unbelievable! This was an important Christmas present. No way to run a business. We will never give him our business again. He can not be trusted and I hate to think how he would honor a guarantee. BH.

American/Holiday was a surprise find in the St. Michael's area, as their 2nd location in Georgetown…read moreclosed years ago. This store is large and spacious, featuring local artists, cute ducks and hand-knitted sweaters, furniture, decor, and apparel. Staff are friendly, but a little pushy. They have a great sales/clearance section for seasonal items, so stock up! +cute ducks and sweaters +local artist features +sales/clearance items +slightly pushy staff

Bottom Line: Fun and funky decor, clothing and gifts located inside an old bank…read more What I like about American Holiday is that it is unique and stays on-brand. Upon entering I felt like I had been in the store before . . . and I had, in its old Georgetown location. That must have been quite awhile ago because American Holiday has since relocated to an Old Bank in Saint Michael's. The store has a dark, cozy and expensive boutique feel to it although many of the items seem reasonably priced. I love the quirkiness of the faux-taxidermied stuffed bear heads, ohh, only if I was cool enough to hang one of those whimsical, grizzlies in my house. We looked at some of the games and knick-knacks and I thought seeing the old, albeit not that old, bank vault was cool. The old night deposit is still there too.

Excellent food selection, knowledgeable and friendly service, clean cute, always a great place to…read morestop in St. Michael's!

Simpatico is a wonderful little shop in St. Michaels that specializes in Italian items (wine, food,…read morekitchen linens, dinnerware, accessories, etc.), and I'm so glad we visited with our friends when we were visiting them in St. Michaels last weekend. It's small, but it has such an amazing inventory. I loved that they sell wine from every region of Italy, and we took home some great wines from Friuli-Venezia Giulia. Their food products were also great, and I'm a little jealous that we don't have a shop like Simpatico near us in Baltimore. Because I'm sure I'd be here all the time. Not just to shop but for classes, too!

What the Sail? Did you know Sea Bags will recycle your sail into a functional and cool product,…read moresuch as a cooler bag, tote or coin purse? I had no idea! I happened to stumble into this store while vacationing in St. Michael's and was fascinated by all of the retail items for sale. I bought a cute blue coin purse with an anchor emblem, as well as a knotty keychain. :) I got both for $25. The cashier was very friendly and answered all of my questions regarding recycling my sail (that's been living in my basement for several years). The receipt has her named as Bridget so hopefully it was actually Bridget I was speaking to. I can't wait to get my sail repurposed into products I will actually use, as well as keep it out of the landfill. Yay!

it's 2pm and your closed ??? .................. Been here…read morefor 20min and nobody is here, Friday was the same are you moving locations ?

I walked in not expecting to find anything I would like much less something in my size. Mr Hessing…read morelooked at my feet while in a tennis shoe and said you wear a 10 slim. Try this shoe on. I was skeptical since I wear a 9 narrow most of the time. I put the shoe on and I have to admit, they were more comfortable than my favorite slippers! I almost said not to buying them as they were in a color I don't usually wear but hey, who could not buy the most comfortable pair of shoes I've had on in years! I was quite impressed and want more in my real size!