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

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....

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!

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

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.

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.

Bottom Line: A gorgeous store front that unfolds to flowy easy styles and pretty jewelry for…read moreladies. Main Street in downtown Annapolis is undeniably quaint as a whole but the striking storefront of Lilac Bijoux always catches my eye. I love the unpredictably light purple store front with the cream color, hefty and significant dentil molding. The classy and stunning facade is the perfect foreshadowing of the lovely styles inside. Lilac Bijoux is a boutique for women offering flowy, pretty clothes and accessories. What I appreciate about this store and that they sell jewelry from local designers. The store is small but packed full of good stuff.

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.

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!