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Favorite Shops in St. Michaels, Maryland

St. Michaels, Maryland is one of the Eastern Shore's most charming shopping destinations, offering visitors a walkable collection of boutiques, art galleries, antique stores, specialty gift shops, and locally owned businesses. From coastal decor and clothing to jewelry, handcrafted goods, and the perfect souvenir, you'll find a variety of one-of-a-kind shopping experiences just a short walk from the Log Canoe Inn.

Shops Within Walking Distance of Log Canoe Inn

Chesapeake Bay Outfitters

Chesapeake Bay Outfitters is a locally owned outdoor store in downtown St. Michaels, Maryland, near the waterfront. The shop carries outdoor apparel, fishing gear, kayaking and paddleboarding accessories, footwear, polarized sunglasses, and equipment for boating, paddling, hiking, and other Chesapeake Bay activities.

Visitors can also browse Chesapeake Bay gifts, coastal home décor, locally themed merchandise, and casual apparel. The store is a convenient stop for travelers looking for outdoor gear, waterfront clothing, or St. Michaels souvenirs.

(410) 745-6388
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Distance: 0.1 Miles

Studio 2 Saint Michaels

Studio 2 Saint Michaels is a fine art gallery on South Talbot Street in downtown St. Michaels, Maryland. The gallery features rotating exhibitions by established and emerging artists, including work inspired by the landscapes, waterways, wildlife, and cultural heritage of Maryland’s Eastern Shore.

The gallery is located in a historic building that includes a 19th-century theater designed by architect Edmund Lind. Visitors can explore regional art, changing exhibitions, and cultural events in a setting that connects the artistic and architectural history of St. Michaels.

(518) 253-3373
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Distance: 0.1 Miles

Chesapeake Trading Company

One of Saint Michaels' most popular lifestyle boutiques, this eclectic shop features coastal-inspired home décor, books, gifts, apparel, accessories, jewelry, and unique Chesapeake Bay treasures. Visitors will find an ever-changing selection of locally inspired merchandise perfect for gifts or vacation keepsakes.

(410) 745-9797
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Distance: 0.2 Miles

The Preppy Redneck

A favorite downtown boutique offering Eastern Shore-inspired apparel, gifts, accessories, home décor, and locally themed merchandise. This shop blends coastal style with Maryland personality and is well-known among visitors looking for distinctive Saint Michaels souvenirs.

(410) 745-8072
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Distance: 0.2 Miles

Guilford & Company

Guilford & Company is a jewelry boutique on North Talbot Street in downtown St. Michaels, Maryland. The store specializes in antique, estate, and fine jewelry from the Victorian, Art Nouveau, Art Deco, and Art Moderne periods.

Owned by Graduate Gemologist Julie Moriarty Hockaday, the boutique offers an evolving selection of jewelry from established designers and jewelry houses. Services include custom jewelry design, restoration, repairs, gemstone sourcing, and professional guidance for special purchases and milestone gifts.

(410) 745-5544
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Distance: 0.2 Miles

Book Hounds

Book Hounds is an independent bookstore on Talbot Street in downtown St. Michaels, Maryland. The shop carries new, used, rare, and out-of-print books, with selections in fiction, nonfiction, history, maritime topics, Chesapeake Bay titles, children’s books, collectibles, and hard-to-find editions.

Visitors can browse regional books and literary finds that reflect the history, culture, and maritime heritage of Maryland’s Eastern Shore.

(410) 745-4600
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Distance: 0.2 Miles

The Christmas Shop

The Christmas Shop is a year-round holiday store in St. Michaels, Maryland. The shop offers Christmas ornaments, seasonal décor, collectible figurines, nativity sets, holiday villages, personalized gifts, and festive home accents.

Visitors can browse multiple rooms of traditional and contemporary Christmas merchandise, including handcrafted ornaments and seasonal collectibles. It is a convenient stop for holiday gifts and Christmas décor at any time of year.

(410) 745-3422
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Distance: 0.2 Miles

The Bench

A stylish coastal clothing boutique featuring premium apparel, hats, accessories, and lifestyle brands for men and women. The shop is known for its relaxed Eastern Shore style and curated collection of quality clothing.

(443) 453-6858
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Distance: 0.3 Miles

Stay Near the Best Things to Do in St. Michaels

Log Canoe Inn places guests near the harbor, downtown restaurants, shops, museums, and waterfront activities. Explore the inn’s six rooms and check availability for your visit. Traveling with a family? We also have a family-friendly cottage just 4 miles from the inn. 

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