Old Town Busker Guide

Are you a musician, artist, or performer who wants to show off your skills on the Loudoun Street Mall? Check out this quick guide we’ve put together to help you get started.


  • Check out your intended spot! Is it directly in front of a business entrance? Does it block foot traffic or impede access onto the mall? Is someone else already set up close by? If so, please look for someplace new.
  • Consider walking in and introducing yourself to someone at the businesses nearest you. It will make your time as a busker easier and friendlier!
  • Want tips? That’s fine! There’s nothing wrong with placing a jar or case down to collect dollars and cents, but you can’t solicit people walking by–and you can’t sell anything without a business license and a vendor permit, so be mindful!


  • If you’re playing acoustically, you’re good to go! Feel free to take your guitar (or mandolin, flute, harmonica, voice, cajón, etc) and strike up a tune. Just be courteous and don’t get so loud that we have to bring a decibel meter downtown.
  • Bringing an instrument downtown is fine, but anything that requires you to set it–or accompanying equipment–down on the ground is going to have to be able to stay out of the way. You can’t block the right of way, obstruct business entrances, impede foot traffic, or set up on the property of any business or museum without their explicit permission. We work hard to keep our downtown accessible to all! If you have questions or concerns, just give the Old Town office a call and we’ll try to help determine the best move.
  • If you are planning to play with amplification of any sort–even if your amp is battery-powered and independent–you are required to have an amplification permit. Permits are $10 and require an application to be filed with the Old Town office.


  • Just looking to get in some plein air painting or bring a sketchbook out into the sun? Awesome! You’re good to go–tag us at @oldtownwinchesterva when you’re done!
  • If you’re interested in selling any of your pieces downtown, that’s great! Just know that first, you’re going to need a business license and vendor permit–so plan in advance, and give yourself plenty of time to get both squared away.
  • Want to get involved with our First Friday art walks? Send an email to otw@winchesterva.com and we’ll put you in touch with the people who make it happen! We’d love to have you!


  • Maybe you’re a juggler, dancer, ribbon artist, face painter, or balloon wrangler? A mime, magician, or sword swallower? (Please no sword swallowing.) We’d love to see you down here! Just respect the right of way, and don’t solicit any passerby. In order to sell anything, you need a business license and a vendor permit, and if you have equipment you need to set up for your act, you’re going to need a permit for that as well.
  • If any part of your act involves amplification, even battery-operated mics or speakers, you have to apply for an amplification permit. Permits are $10 and require an application to be filed with the Old Town office.

If you have any other questions, don’t hesitate to reach out to Jenny McDonald! Thanks for keeping Old Town vibrant!

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