Photo Submitted to: The Baltimore Times

Each year The historic Upton Planning Committee and Pennsylvania Main Street host an exciting community festival named after Baltimore’s own, Ms Billie Holiday. The Billie Holiday Festival is a Free music and arts festival that showcases various regional bands, community groups, vendors and local talent. This year’s festival is happening this Saturday September 2, 2023 at 1201 Pennsylvania Ave. from 10am to 7pm.

WE sat down with Wanda G Best, Executive Director, Upton Planning Committee, Inc.(UPC) and BHF2023 organizer to discuss this year’s festival:

Baltimore Times: Hello Ms. Best, Why Billie Holiday?

Wanda Best: Billie Holiday because she once lived in West Baltimore and is one of Baltimore’s most famous citizens. The statue of Ms. Holiday is erected at the corner of Lafayette Avenue and Pennsylvania Avenue, a beautiful creation of Mr. Reid (deceased).

Baltimore Times: When did the Billie Holiday Festival first start?

Wanda G Best, Executive Director, Upton Planning Committee, Inc.(UPC) | Photo Submitted to The Baltimore Times

Wanda Best: The UPC organized the first Billie Holiday and Arts Festival 5 years ago. It is an annual event that represents the Historic Pennsylvania Avenue Main Street. Historic Pennsylvania Avenue is one of eight Main Streets in Baltimore City and UPC manages the program. The Main Street stretches from Martin Luther King Boulevard to Fulton Avenue and one block East; and one block West. BTW – We are currently looking to hire a Main Street Manager.

Baltimore Times: What can people expect at this Year’s Festival?

Wanda Best: This is a free festival and we use this opportunity to provide entertainment that is family friendly and inter-generational. The event includes music,art and dozens of vendors. One important treat is to always include a vocalist that performs Billie Holiday Songs. This year’s performer will be Dr. Jasmine Blank Jones. There are numerous live entertainers coupled with DJ performances. A local personality is always Mister or Mises Ceremony. This year it is April Watts. The festival provides an opportunity for non-profits to share information on numerous topics for improving and maintaining one’s health and well being. It’s also an opportunity for small businesses/entrepreneurs to share their wares. This year, vending is free on first come first serve basis (space is limited) for vendors that will commit to participating in free small business technical assistance workshops. Our goal is to attract more small businesses to the Historic Pennsylvania Avenue commercial corridor. So bring your chairs, and blankets and enjoy a great show.

Baltimore Times: Thank you so much for taking time to sit and talk to us. You can find out more information about this year’s festival by visiting the festival’s website:

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