News & Events

Old Town Winchester Sign
News

Get A Look At Old Town Winchester

Old Town Winchester is a special place, and a little bit of its magic has been captured in a new video produced by 44 Outdoors.  The clip takes a look...

June 14, 2014
Events

Fiddles & Fifths

Join us for our third annual Fiddles & Fifths Bluegrass and Bourbon Festival on Saturday, September 14 in the heart of Old Town Winchester, VA! We...

July 5, 2024
Events

Rockin’ Independence Eve

Celebrate our nation’s independence a day early! Join Old Town Winchester July 3rd from 2–7 PM for great food, family activities, and live music...

June 18, 2024
Events

First Friday

First Fridays are back! Every first Friday of the month [weather permitting], we host local artists, live music, sip & stroll, special events, and...

June 4, 2024
Events

KidzFest! 2024

Join us in Old Town Winchester on Saturday, June 8 between 12-5 PM to experience a fun, free day out for the whole family as we partner with our frien...

May 16, 2024
Events

First Friday

First Fridays are back! Every first Friday of the month [weather permitting], we host local artists, live music, sip & stroll, special events, and...

March 29, 2024
Events

Old Town Winchester Celtic Fest

Join us in Old Town on March 16th from noon to 10 PM to celebrate Winchester’s Celtic heritage with artisan craft vendors, live entertainment an...

February 16, 2024
Events

Black History Month Art Walk

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...

January 30, 2024
Events

Chocolate Escape

Join us in Old Town on Saturday, February 10th from 2–5 PM for our 11th annual Chocolate Escape! For just $5 each you can sample some incredible choco...

January 22, 2024