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 Values

• Present Authentic Cultural Experiences: We believe that creating an authentic corridor that preserves a sense of local flavor and place is essential, so we create activities that reflect local interests, Annapolis’s rich historic identity, and elements of our quirky character.

• Boost and Inspire Creativity: Our activities are especially designed to enhance the arts, entertainment, and cultural offerings of Annapolis and support hundreds of artists, musicians, and performers annually. These creatives help celebrate, sustain, and share Annapolis’s diversity and vitality, ultimately enhancing our quality of life. 

• Support Diverse Community Connections: Our team of business-owners, creatives, neighbors, colleagues, and friends works together to deepen a shared sense of community and ensure that West Street is a place where everyone feels a sense of belonging. 

• Sustain a Safe and Welcoming Thoroughfare: We strive to create hyper-local gathering spots and physical spaces where neighbors and visitors can interact comfortably. Transforming Inner West Street into a walkable, safe, and inviting thoroughfare cultivates community, local pride, and collective investment. 

• Enhance Local Economic Value: Our efforts to facilitate beautification and accessibility projects, improve storefronts, and support artisans and local businesses keep capital within the community, create local jobs, enhance property values, increase the tax base, and support a resilient local economy.

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, Fall Fest on West, the Clydesdale Horses, and more.