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

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!

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....

Beautiful gift shop with the kindest pharmacist. This place has the best small town vibes and if I…read morelived closer, it would be my go-to!

Pemberton Pharmacy & Gifts is off the main drag in St. Michael's, and they have a pharmacy on site…read moreas well as other gifts and decor that you can purchase. We had a great time, perusing through their various items, such as the plushies, the kitchen items, home accessories, and their cosmetics. The place is large, and has a great selection. +pharmacy on site +gifts and accessories

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!

Come by Chance is a higher end boutique of furniture and home decor, and we had a nice time…read moreperusing their selection. Their marble tables and their platters were beautiful! Staff were friendly and allowed patrons to look around in a comfortable setting. +pretty dishware +friendly staff

Lots of boutique shops in this town, and this one is just a tiny more upscale than most. Really…read morelovely smelling candles, dinner ware and deco. I loved the paintings on the walls with the hues of the water. Some of the furniture looked like it belonged to a Diane Keaton movie - if you know what I mean, you know.

Great little shop in St. Michaels! It is one of my daughters favorite stops when in town…read more Adorable pieces of quality silver jewelry for all ages at very reasonable prices. Service is always warm and friendly. Anyone who can help (& tolerate) a solo-shopping dad find the perfect gifts on Christmas Eve has earned extra credit in my book! Thanks for providing a quaint shop for us weekend visitors. A perfect match for those strolling and shopping in St. Michaels!

Adorable shop with cute things, but more of the same ole stuff you find at craft vendors. New stuff…read morethere is already been done. But polite staff.

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.

We were informed upon walking in that my 10 year old daughter wasn't allowed upstairs without an…read moreadult. Geez, what the heck is she going to do up there that requires an adult escort? She likes to find knick knacks for us to buy. After that we felt very unwelcome and just left. So rude. Their rudder isn't going to be the only broke thing if they don't reconsider their customer service strategy.