1. Chick & Ruth’s Delly
165 Main St.; 410-269-6737
Run in for a breakfast wrap to enjoy at the dock—staffers will sometimes hold your dog’s leash for you outside, or you can tie up the leash. Arrive by 9:30 on weekends or 8:30 weekdays, and you can join in the Pledge of Allegiance.
2. Watermark
410-268-7601
At the City Dock, have a seat at a bench and watch yachts and sailboats swan in and out. Tempted to go aboard? Watermark offers a variety of outings, from 40-minute to daylong excursions, all dog-friendly.
3. Visitors Bureau
26 West St.; 410-280-0445
Pick up a map here, where one-hour Discover Annapolis trolley tours (410-626-6000) depart. If the windows are open, your pup can hang his or her head out and enjoy the breeze.
4. Annapolis Running Shop
172 Main St.; 410-263-0010
Say hi to Gordy, a rescued Weimaraner and the shop’s resident dog.
5. Peppers
133 Main St.; 410-267-8722
Navy and Marine Corps gear for all ages.
6. Shades of the Bay
136 Main St.; 410-267-6663
Forgot sunglasses? At this store, you can meet Allie, a 12-year-old beagle that has performed in TV commercials.
7. Helly Hansen
132 Main St.; 410-990-4359
The marine-style gear is beloved by sportspeople and fashionistas alike.
8. Zachary’s
100 Main St.; 410-266-5555
In the mood for diamonds? Zachary’s welcomes canine browsers, too.
9. McGarvey’s Saloon & Oyster Bar
8 Market Space; 410-263-5700
Snag an outdoor table for seafood or a burger to share with your pup.
10. The Annapolis Bookstore
35 Maryland Ave.410-280-2339
Specializes in new and used maritime titles, classics, and children’s books.
11. Blue Crab Antiques
55 Maryland Ave.; 443-949-7055
Welcomes pups despite precious breakables.
12. Harry Browne’s
66 State Cir.; 410-263-4332
A dog-friendly spot for lunch or Sunday brunch, which starts at 10.
13. Paws Pet Boutique
64 State Cir.; 410-263-8683
Annapolis-themed biscuits plus high-quality leashes and toys.
14. The Annapolis Pottery
40 State Cir.; 410-268-6153
The pottery is made in-store and by artists nationwide. The proprietors don’t fear wagging tails attached to small dogs.
15. Easy Street Gallery
8 Francis St.; 410-263-5556
One of the country’s top American crafts retailers.
16. Annapolis Ice Cream Company
196 Main St.443-482-3895
Don’t miss the house-made apple pie mashed into house-made vanilla ice cream. Say you have a dog waiting outside and you’ll get a free small doggie portion.
17. Loews Annapolis Hotel
126 West St.; 410-263-7777
On Friday evenings, check out Canines & Cocktails for a Cause.
