Maryland Avenue is long-treasured as one of downtown Annapolis’ best spots for shopping, dining, and experiencing the culture. Below you’ll find a guide to experiencing that culture while saving a buck or two. Truly, you could spend all day on Maryland Avenue, so plan accordingly!

~ This page has been updated to reflect 2018 events and happenings. ~ 


The Hammond-Harwood House’s goal is to bring history alive through events, tours, and educational programs. True to form, the historic landmark hosts several events that relate colonial times to a modern audience. 

If you want to support Hammond-Harwood while staying within the beautiful comfort of downtown Annapolis, attend the Pumpkin Walk on October 20 from 4 to 6 p.m. This event takes place at the Maryland Avenue location but also features a march down the street. The Pumpkin Walk is suited for children–bring yours and dress them up for Halloween! In addition to the Halloween costumes and march, there will be games and other activities to keep everyone entertained.

It’s accurate to say Hammond-Harwood House is lovely at all seasons, but December sees more decorations in the house and garden. Tour the grounds at the end of the year and observe for yourself its unsurpassed beauty. During November and December, the house is available for touring Tuesday through Sunday from noon to 4 p.m. Admission for adults is $7; children’s admission costs $4; senior citizens and students must pay $6 to tour the museum. Touring during April through October costs the same, but tour time is extended one hour. Call 410-263-4683 or visit to inquire further. There’s a link at the bottom of the “Visit” page that offers coupons for touring as well. Hammond-Harwood House is located at 19 Maryland Avenue.

The Maryland State House is located at 100 State Circle just off Maryland Ave., and even if you’ve never been to Annapolis before, you won’t be able to miss it. It’s the oldest U.S. state house still in legislative use, and while there are no formal guided tours, you can embark on a self-guided tour and explore the history and the astounding architecture of the State House. 


Staying in an exceptional hotel, inn, or bed and breakfast exponentially enhances any vacation. The joyful sentiment is further increased when that lodging offers specials and discounts. Such is the case with Inn at 30 Maryland. The establishment set up a way to make staying there more enjoyable with flowers, food, and wine for varied prices. Fresh flowers in the room costs $45, an assortment of cheese, crackers, and fresh fruit costs $30, and a bottle of wine costs $40. Can’t decide on just one? Choose two and save $5 or combine all three and save $10 on the whole price. In addition to these specials, book online with the inn and save $10 per night.

The off-season at Inn at 30 Maryland sees discounted rates as well. Stay in Suite 35 (sleeps four, with a private bath and balcony) from January to April or July to September and enjoy $219 per night as opposed to $269 per night. Room 34 (sleeps two) features a $30 discount during the same months. Room 33 (sleeps two) and Room 32 (sleeps two) also see a $30 decrease for the same months. Suite 31 has a balcony, private bath, and sleeps four. Book this accommodation January to April or July to September for $219 instead of $269. Go to or call 410-263-9797 to learn more on this lovely overnight option.


You probably never thought you would see a barbershop on this guide to savings! Capistrano Barbershop is extraordinary and coupled with its coupon available on, it belongs in this guide. The discount rewards new clients 20% off a first haircut or shave. The barbershop is located at 54 Maryland Avenue, but pick up the coupon on their site.


63 Maryland Avenue is home to one of the most locally and nationally recognized restaurants–Galway Bay Irish Pub. Featured on Food Network’s Diners, Drive-Ins and Dives, Galway Bay features hearty sandwiches, Irish fare, and even Irish egg nog. The beloved pub hosts daily specials that can range from chicken macaroni and cheese to lemon pepper calamari. You can find the day’s special here:; the specials are updated daily. Galway Bay offers other specials too, like $5 burgers on Monday and happy hour deals Monday through Friday from 3 to 6 p.m. Galway Bay shows they have the spirit of a true Annapolis business in hosting the 3rd Annual Guinness Cruise. In partnership with Watermark Cruises, the Irish establishment provides the food. Guinness will gladly overhaul the drink table, replacing boring drinks with its deep, frothy goodness. Tickets are limited; purchase online at the website provided above or at Galway Bay’s sister restaurants: The Killarney House or The Brian Boru.

This list is as comprehensive as possible, although some businesses along Maryland Avenue do not have websites or specials they advertise. By nature, most stores must put merchandise on sale at varied times. Artwork, cigars, antiques, and CDs go on sale. There are plenty other wonderful establishments on Maryland Avenue (and all of Annapolis, for that matter), that are worth your time. As one of the longest and most packed streets in downtown Annapolis, window-shopping and strolling Maryland Avenue will lead to great finds and adventures. Use the guide here for specials, but don’t forget about the other places to visit on Maryland Avenue!