Cute little shop with local artist gifts. Adorable children's books and very nice and expensive…read moreclothing. Out of my price range but worth perusing. Nice service. Nice selection of books for all ages, too. I miss brick and mortar bookstores so this was a treat.

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!

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 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.

The crew at The Bench is awesome! They were so helpful and kind and made the experience super fun…read more I customized a cutie hat and a pouch for my mom. Can't say enough great things. Special shoutout to our king, Cam!

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!

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.

I'm writing this 80% for the service I received and 20% for the merchandise. To be clear, I really…read moreloved quite a few of the clothing and accessories here. Even though the style of the pieces seemed to be going through a bit of an identity crisis, I saw enough I really liked to definitely come back (and I bought a few things). Their jewelry was also exceptionally cute. But what inspired me to write this was the great service I got from the person working that day. It was just one girl working and I think her name was either Sophie or Sophia. She had the coolest and nicest personality and made my entire visit just a pleasant experience. No matter what the likelihood was of not having my size in stock, she always was more than happy to check the back and she was engaged and helpful throughout my visit. She was the only person working and I noticed even when it got busy she took the time to greet & acknowledge everyone that came in the door. I know this is a long post but having had my share of rude and/or ambivalent salesperson experiences, I consider myself a customer service snob so when I get great service I take note. A big thanks to Sophie/Sophia for making my shopping visit enjoyable. I will be returning!

An adorable boutique in downtown Annapolis near the shops, restaurants yards away from boats/yachts…read moremeandering in the inlet of the bay. The store is small but has a bounty of clothing given varying taste. I stumbled upon a lovely pair of printed flowy black & white pants which were a must have. Also, grabbed a pair of sweaters and tops to add to my wardrobe. Many of the items are trendy but you can find a few staple items. This is a boutique so the prices tend to be a bit pricey. Somethings are worth the added value yet some of the designer items don't seem to be the best quality. I suggest this place for those who like trendy pieces and if you like pieces you can mix and match.

This Beautiful shop has something for everyone!! The kid's clothes and games and books are…read moreperfect!! I bought some very unique pieces of jewelry that get compliments every time I wear them. Enjoying seeing the local artists work's being sold too! And then a sweet for the road! Perfect shopping spot!

You know those ubiquitous gift shops where everything ceramic had words that demand action from you…read morelike EAT / ENJOY / LIVE LAUGH LOVE? Yeah, this store pretty much had it. Lots of home decor like plates, candles, jewelry, some clothing items. Nice staff, fair pricing.