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  • Tutu Tuesday
  • Dinner Under the Stars
  • First Sunday Arts Festivals
  • Chocolate Binge Festival
  • Fall Fest on West
  • Scarecrow Stroll
  • Motown
  • Clydesdales
  • Arts Week   

The Inner West Street Association is committed to bring art and entertainment to the streets of Annapolis!

Dinner Under the Stars is supported by the local restaurants on the street featuring outdoor dining and music on every Wednesday and Saturday May thru September with themed nights for a night of fun, dining and dancing.  

First Sunday Arts Festivals May thru November brings over 100 vendors to Inner West Street and People's Park which visitors can stroll the street shopping for hand made and creative art.  We offer a variety of music for entertainment from local musicians on 2-3 stages during the festivals.


The famous Annapolis Chocolate Binge Festival is a favorite event held the first Saturday of December which offers over 40 chocolate vendors to show off their chocolate creations  for all to purchase.  We also feature numerous art vendors, music and dining specials from our variety of restaurants.


Plus additional fun festivals such as the Tutu Festival, Fall Fest on West, the Clydesdale Horses and more.    

We have a street like no other in town!  Your support allows us to continuously provide all these forms of arts and entertainment to the Annapolis community and beyond.  

We thank you for your contribution!  

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