Hobo Bags (194 Green St)

Founded in Annapolis in 1991- filled with leather bags and wallets. Check out my post with the founder of Hobo here.

Hats in the Belfry (103 Main St)

Every style of hat at every price point. Open for over 30 years!


Evergreen Antiques (69 Maryland Ave)

A special find for everyone- you won't leave empty-handed. 

Natalie Silitch (62 Maryland Ave)

Mixture of European antiques, unique gifts, art, and handmade ornaments in a beautiful setting. Collectors visit her from all over the country. 

Art Supplies

Art Things* (2 Annapolis St)

Family owned supply shop in charming West Annapolis.


The Annapolis Bookstore (53 Maryland Avenue)

Check out their website- they host lots of events!

Back Creek Books (194 Main St)

Old Fox Books (35 Maryland Ave)

Also home to the sweetest coffee shop, Brown Mustache Coffee, and the cutest backyard.


Candles Off Main / Annapolis Candle* (2444 Solomons Island Rd)

A gem. Every candle under the sun- must visit. Husband and wife team also produce Annapolis Candle at this location. Candle making workshops as well.

Ceramics and Crafts

The Annapolis Pottery (40 State Circle)

Easy Street (8 Francis St)

American craft gallery- I especially love the glass pieces. 

The Green Phoenix (141 Main St)

Coastal Apparel

The Lucky Knot (176 Main St)

Lots of preppy labels, all under one roof.

The Pink Crab (30 Market Space)

The Lilly Pulitzer Signature Store- especially popular around croquet.

Tyler Boe (162 Main St)

Classic and elegant staples- the other shop is in Newport.


One Petticoat Lane* (2 Annapolis St)


Wrabyn* (12 Annapolis St)

Hard to find contemporary lines (for Annapolis), like A.P.C. and Apiece Apart.

Fine Jewelry

Way Off the Beaten Path (216 Main St)

Favorite store in Annapolis. More here.

Sparrow Collection (198 West St)

Indie mid-range and high-end jewelry- has a cosmopolitan vibe.

La Belle Cezanne (79 Maryland Ave)


Annebeth's (46 Maryland Ave)

Local favorite- wine/beer, a light selection of groceries, and tons of gift options!

Capital Teas (77 Main St)

Seasons Olive Oil & Vinegar (180 Main St)

Huge fan of their fig balsamic vinegar and lemon olive oil- you can taste test anything!


Kokopelli (149 Main St)

Overflowing with unique products in every nook and cranny.

Whimsicality* (1350 Cape St Claire Rd)

SCOUT Bags destination store (plus so much more!) run by mother-daughter duo. I featured them in this post.

Here. A Pop-Up Shop* (changes)

Extremely popular shopping events with an assortment of goods by local artists.


Natalie Silitch (62 Maryland Ave)

The Peake House (76 Maryland Ave)


Lil Lamb Boutique (44 Maryland Ave)

They also host birthday parties and events.

Wheat (201 Main St)

Danish chic for children.


Mr. Scherfel (88 Maryland Ave)

Curated boutique filled with sportswear and denim- cool labels.

Capital Custom Clothiers (50 Maryland Ave)

Well respected bespoke menswear shop.

The Lucky Knot (176 Main St)


Paws Pet Boutique (64 State Circle)

One of the most loved shops in downtown Annapolis- there are always cute dogs visiting.


KA-CHUNK!! Records (78 Maryland Ave)

Old school indie record store- the owner is very knowledgeable.

Resort Apparel

Way Off the Beaten Path (216 Main St)

Unique clothing designed by mother and daughter team- only available through them directly! Pieces are cut in small runs and sell out each season.

Sailing Apparel

Helly Hansen (132 Main St)

Quintessential sailing gear- everyone in town owns something from here.

Sperry (36 Market Space)

Trend Apparel

Lilac Bijoux (145 Main St)

Sweet jewel box of a shop, filled with jewelry, clothing, and accessories at accessible price points.

Brown-Eyed Girl (234 Main St)

Brimming with lace, crochet, embroidery, fringe, and flowy dresses. 

3 Sisters (170 Main St)

*more than a 20 minute walk from city dock- you may need a car or bike.