Where to shop in St. Michaels Maryland like a local


Anyone living in Washington, D.C. or visiting the area wouldn’t necessarily look twice at Eastern Shore Maryland across the Bay Bridge as a shopping destination. Everything you need is right in the city, isn’t it? Not if you love to shop local. My first excursion over to St. Michaels made me wonder why I hadn’t been there before. There are so many amazing places to shop in St. Michaels Maryland that are locally run and owned by the residents. It’s hard to find a chain store in town.

I was glad I brought my SUV on the trip. Smart clothing boutiques, great home décor stores, one amazing woodcraft artisan shop, and an estate jewelry store that would make Audrey Hepburn’s Holly Golightly cry real out in sheer bliss is what makes shopping local in St. Michaels, Maryland so special. I mean really, when the handcraft candy store also sells accessories in the back, how can you go wrong with a trip to Eastern Shores Maryland.

St Michaels Maryland

Shopping in St. Michaels Maryland

Knotty Living, 214a S. Talbot Street, St. Michaels, MD 21663. One of my favorite places to shop in St. Michaels is Knotty Living. This boutique-clothing store is small, but carries the latest trends and a few basics you may need to pull them off. Best of all, the sale section is incredible, making something that might have been out of your price range at the beginning of the season suddenly within your budget as the season draws to a close.

American Holiday St Michaels (A/H), 300 S. Talbot Street, St. Michaels, MD 21663. This sister store to Knotty Living features mostly home décor. Like the clothing boutique just down the street, A/H carries unique items you won’t even know to look for online or at your shops back home. The displays show off each piece so you aren’t overwhelmed and make it fun to imagine each item in your house

St Michaels Maryland

Pizazz, 100-A South Talbot Street, St. Michaels, MD 21663. If you love digging through a new jewelry box, you will adore Pizazz. This shop hits just the right price point for anyone looking for costume jewelry or more delicate every day pieces. The scarf collection is decent, and the owner carries a small selection of bags, sunglasses and hats. Go in, try stuff on and have fun while you shop in St. Michaels!

Chesapeake Trading Company, 102 S. Talbot Street, St. Michaels, MD 21663. As soon as you walk into this shop you will want to breath deeply and then find the NEST Grapefruit candle that has created that enticing smell. I instantly knew that this was how my bedroom should have smelled my entire life (especially during the diaper years with my kids). The shop carries a well-curated collection of men’s and women’s fashion, including Billabong, TOMS and Ray Bans. There are a few cute Maryland themed purses and scarves available as well, for those who like to wear their state pride.

The Christmas Shop, 216 S. Talbot Street, St. Michaels, MD 21663. Everyone needs to pick up a Christmas ornament when they visit a new place. This shop is filled with every kind of ornament you could desire, but if you want something that is locally made and really shows the flavor of Eastern Maryland, ask at the front desk where the local ornaments tree is located. Grab a sailboat or crab in a cage to remember your visit when the holidays arrive.

Guilford and Company, 101 North Talbot St., St. Michaels, MD 21663. As the employees like to say, this is a store that provides grown ups with a little dress up time when shopping in St. Michaels. The store is beautifully laid out like a Tiffany’s or Cartier’s, but ninety percent of the store is antique and estate jewelry, some dating back to the Victorian era. It will be hard for the average person to find a trinket to bring home from their travels in this shop, as one gorgeous art deco engagement ring I tried on was priced at $8500. The gold chocker I fell in love with was $12,000. If you are looking for a unique piece that you will never find anywhere else, this is the store to come to or hint for your husband to pop into when he needs your next anniversary present.

St Michaels Maryland

Simpatico, Italy’s Finest, 104 Railroad Avenue, St. Michaels, MD 21663. If you are like me and you enjoy fine wine and picking up olives for your husband, you must stop into Simpatico. The owner hand selects items direct from Italy to be sold in her shop, whether it be pottery, pasta, limoncello, wine or even cheeses. She also has a house line of jarred olives, tapenades and artichokes. Not sure what wine or cheese you will enjoy? Simply ask the owner, who is usually at the counter greeting everyone as they come in and helping you make a purchase you will be happy with and want to pick up again and again.

Pemberton Pharmacy & Gifts. 204 S. Talbot Street, St. Michaels, MD 21663. This is no ordinary pharmacy. You can buy the medicine you need, but you will also find $50 ponchos, warm scarves, greeting cards and cute bags you can all too quickly convince yourself you can’t live without.

St Michaels Maryland

The Plaid Zebra, 112 N. Talbot Street, St. Michaels, MD 21663. If you are looking for a shop that carries it all, The Plaid Zebra is your spot. Walking in you’ll find loads of odds and ends for your house, while in the back is a treasure trove of children’s fashions, games and toys.

Antiques on Talbot, 211 N. Talbot Street, St. Michaels, MD 21663. Locals in the know tell their friends to head to this antique shop for oyster plates when shopping in St. Michaels. Walk in and say hello to the lovely owner who sits on her stool at the front of the shop and answers any questions you might have. The shop is small, but it is packed with beautiful china, nautical-themed items, furniture and more.

St Michaels Maryland

Woodcraft Artisans, 200 S. Talbot Street, St. Michaels, MD 21663. If you are a connoisseur of beautiful, handcraft art than Woodcraft Artisans is a must. I went a little crazy over the laser-cut layered nautical maps, picking up the Hawaiian Islands, Salish Sea and Outer Banks maps that were carefully framed in wood and glass to protect every detail of the artist’s work. Furniture and sculptures are also available, but you will want to go in for the maps (also available in their Annapolis location).

St. Michaels Candy and Gifts, 216 S. Talbot Street, St. Michaels, MD 21663. Ice cream, candy, earrings and bracelets— what more could a girl want when she is shopping in St. Michaels Maryland? Walking in you will think this store only offers handcrafted chocolates and ice cream, but the farther back you go the more the merchandise changes from sweets to accessories. Poke around. Find a new bracelet, necklace, bathing suit cover up or ring to remember your trip. Don’t be surprised if you see the owners in there either. They are hands on and like to pop in to check on things.

Inn at Perry Cabin St Michaels Maryland

Where to stay in St. Michaels, Maryland

Inn at Perry Cabin by Belmond308 Watkins Lane, St. Michaels, MD 21663-2114. Luxury, gorgeous views and fabulous food come together at the Inn at Perry Cabin. This is the ultimate hotel for a girls getaway or couples weekend. There is a spa, restaurant, and more than enough adirondack chairs to watch the sunset and sip on a glass of wine. Check prices and availability here.

St. Michaels Harbour Inn Marina and Spa101 N Harbor Rd, St. Michaels, MD 21663-2910. Couples and families will love this inn at the marina. Breakfast is included in your stay and there is a pool for the kids to splash around in after you explore Maryland’s Eastern Shore. Check prices and availability here.

Parsonage Inn210 N Talbot St, St. Michaels, MD 21663-2102. If you are looking for beautiful old home to drop your bags at and take a quick cat nap in between shopping in St. Michaels Maryland, the Parsonage Inn is your place to call home. Check prices and availability here.

Have you been to St. Michaels Maryland yet? 

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St Michaels Maryland


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  • Annika

    wow. These staffs are perfect for Christmas gifts and some of those are antiques. Thanks for sharing.

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