Inner West Street Association (IWSA) Purpose

Since 1989, we have been dedicated to ensuring that Inner West Street is a critical hub for social, cultural, and economic activity, while preserving the area’s unique character and heritage. We strive to be the backbone for social connection by creating gathering spots and hosting events that bring neighbors and visitors together within and surrounding the City of Annapolis’ historic West Street and the Arts and Entertainment District. Our community has become known as a destination where neighbors genuinely know each other and the businesses thrive, and we are committed to sustaining the success.    

Our Approach

We develop, promote, and support a diverse range of enjoyable, memorable, and meaningful local festivals, events, and initiatives designed to bring residents and visitors alike enjoyment, discovery, belonging, and an enhanced sense of well-being.   

Our Signature Events

• Dinner Under the Stars features outdoor dining and music at local restaurants on the street every Wednesday and Special Saturdays, from May through September, with themed nights for a night of fun, dining, and dancing.  

• First Sunday Arts Festivals bring over 100 vendors to Inner West Street and People's Park from May through November. Visitors can stroll the street, shop for hand-made creative art, enjoy a variety of music from local musicians on multiple stages, and feast on local culinary delights.

• The famous Annapolis Chocolate Binge Festival is a favorite event held on the first Saturday of December, where more than 40 chocolate vendors show off their delicious chocolate creations for purchase. The festival also features numerous art vendors, music, and dining specials from a variety of restaurants.

• We also facilitate additional entertaining and memorable festivals such as the Tutu Festival, the Clydesdale Horses, and more.​