• Jolly Old Town Storefront Competition

    Deck the mall with boughs of holly…and the rest of Old Town, too! It’s once again time for an old holiday favorite as we partner with the ...

  • Holiday Open House & Winter Market

    Join us for your new favorite holiday tradition! Winter in Old Town Winchester is about to get a bit more magical as we bring back the Holiday Open Ho...

  • Windependent Weekend

    It’s the most wonderful time of the year! The holiday season is upon us, and there’s no better place to do your most important shopping th...

  • Main Street America Workshop

    Let’s get to work! Next week Old Town Winchester will be hosting a site visit from state and national level Main Street staff to assist in creat...

  • Community Stakeholder Meeting

      It’s time for our annual community stakeholder meeting! Please join us Tuesday, October 11 at the new Vibrissa Beer taproom to meet Old T...

  • 2022 Holiday Parade & Tree Lighting

    The Holiday Parade returns to Old Town in 2022! Hosted by Winchester Parks and Recreation, the parade begins at 7 p.m. on Monday, November 28. The par...

  • Winchester Pride

    Winchester Pride returns to Old Town this weekend! The Annual Winchester Pride Celebration is back for it’s 3rd year after a 2 year delay with 5...

  • 1st Ever Fiddles & Fifths a Success!

      Thank you so much to all of our sponsors, performers, attendees, and volunteers who made FIDDLES & FIFTHS such a fantastic event! Check out...

  • Volunteer for Old Town!

    Do you love Old Town Winchester? Are you looking for ways to get involved in making it even better? Whether your skills lie in promotion and social me...

  • 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 toge...

Old Town Winchester News