Direct from Nashville, Tennessee, it’s THE STEELDRIVERS!   What began as a casual jam session over a decade ago has become one of today’s l...

KidzFest is just around the corner! Join us in Old Town Winchester on Saturday, May 13 between 12-5PM to experience a fun, free day out for the whole ...

It’s hard to believe that the first quarter of 2023 is almost in the books already! It seems like just yesterday we were ringing in the new year...

Is spring in the air already? Or is that just the feeling of Celtic Fest, fast approaching? Celtic Fest is back this year for another celebration of a...

In celebration of Black History Month, Old Town Winchester in partnership with Selah Theatre Project and Bright Box presents the premiere of RUTH̵...

Restaurant Week returns February 20-25! The 9th Annual Winchester Restaurant Week, presented by the Winchester Main Street Foundation, provides an opp...

All February long, visit your favorite Old Town businesses to see brand new works of art from local Black artists up on display! We partnered with our...

Calling all artists! Do you want the chance to showcase, demonstrate, or sell your work for free on the Pedestrian Mall? Do you want to meet other art...

Get a little extra sweetness in your life with our 10th annual Chocolate Escape! Join us in Old Town on February 4 from 2-5pm for specials, discounts,...

2023, we’re ready for you! The Main Street program of Old Town Winchester is happy to present the 2023 year-at-a-glance calendar for special eve...