Inner West Street Annapolis

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Inner West Street Annapolis IWSA endeavors to preserve a sense of place and provide authentic local experiences that can foster economic, community, and neighborhood revitalization.

Inner West Street Association is the organization behind Dinner Under the Stars, Annapolis First Sunday Arts Festival, Chocolate Binge Festival, Fringe Festival, and many more events and activities held on historic West Street in Downtown Annapolis. Inner West Street Association (IWSA) is organized to develop, promote and support a diverse and vibrant economy within and surrounding the City of Annapolis' historic West Street.

Take a stroll in downtown Annapolis , Maryland Avenue and West Street and see all the fun Scarecrows-vote for your favor...
10/23/2026

Take a stroll in downtown Annapolis , Maryland Avenue and West Street and see all the fun Scarecrows-vote for your favorite ones!

🎶🍷🍻🍽Our first W**e & B**r Fest on West! Great food, w**e, b**r, music, spin and win prizes, art projects and more! See...
10/16/2026

🎶🍷🍻🍽Our first W**e & B**r Fest on West! Great food, w**e, b**r, music, spin and win prizes, art projects and more! See you there - Grab your tickets!

Join us for an unforgettable experience featuring samples from 8 local restaurants, an impressive selection of 20 domestic and international w**es, refreshing craft b**rs, and live music. Enjoy the day with live music performances that will set the perfect background to your afternoon. Dance, relax,...

10/13/2026

Register today IWSAnnapolis.com

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Annapolis, MD
21401

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