Maryland Avenue and State Circle Association

Maryland Avenue and State Circle Association The Heart of Historic Annapolis Maryland Avenue and State Circle comprise the heart of the historic district in Annapolis. Explore historic houses and gardens.

Unique in charm and character, Maryland Avenue is the oldest commercial street in Maryland and one of the oldest in the United States. Discover several antiques shops and interior design stores. A bookstore and coffeeshop with a charming hidden garden. One of the last independent vinyl record shops; a barbershop and a hair salon. Nourish and replenish at the pubs, inns, and B&Bs. Maryland Avenue and State Circle is the place to have an Annapolis experience!

06/06/2026

One of the few days a year you can enjoy outdoor dining on Maryland Ave, its Art on the Ave 🎨 join us tonight for live painting, live music, and a crisp beverage 🖼️🎶🍺

06/06/2026

Tonight is the Collector’s Party and Juried Artist Awards Ceremony! Join us at Circle Gallery from 6 - 8 PM if you purchased a ticket to celebrate all the incredible work done by our Paint Annapolis Juried Artists.

06/06/2026
06/05/2026
06/04/2026

Email from Evergreen Antiques and True Vintage Paint Annapolis block party 5-7 ART ON THE AVENUE a Paint Annapolis Block Party! returns this Thursday, June 4th, 5-7pm Join us for a lovely summer eveni

06/04/2026

Éric from Imports will be here tomorrow sampling these cool Greek wines for on The Avenue 4-7pm on Maryland Avenue and State Circle Association

Galway Bay Irish Restaurant and Pub will have their beer garden open - plein air artists will be painting, cool jazz from Grant trio will be playing…

Join us for beautiful night!

06/04/2026

We won! Thanks to all of you who voted for us to retain the title of Best Irish Restaurant in Annapolis! Stop in for a pint soon!

06/04/2026

See historic Annapolis through the eyes of talented plein air artists as architecture, charm, and city streets become works of art! Stroll, explore, and experience creativity around every corner.

Address

Maryland Avenue At State Cir
Annapolis, MD
21401

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