Tech-Forward Town: Digital Tools for a Connected Community

Winchester Brew Works

We love hearing from our amazing Old Town community! That's why Friends of Old Town is hosting monthly outreach and input sessions all year long. These laid-back, open-forum meetups are a great chance to share ideas, chat about what's happening in Old Town, and help shape our future together. Each session focuses on a fun, […]

Catalyst Quartet

Bright Box 15 N Loudoun Street, Winchester, VA, United States

Shenandoah New Music Hailed by The New York Times as โ€œinvariably energetic and finely burnished,โ€ the Grammy Award-winning Catalyst Quartet is redefining the classical music experience. Founded by the internationally acclaimed Sphinx Organization, the ensemble is driven by a belief in the unifying power of music and a passion for collaboration, innovation and inclusion. Their […]

$18
Shake Your Booty 70s Dance Night

Shake Your Booty 70s Dance Night

Vibrissa Beer 10 N. Kent St, WINCHESTER, V, United States

70s BABY!!! 70s music and beyond, 70s attire encouraged but not required. Come for Community, Dinner and Drinks -- Stay to DANCE! (or just come to dance!) Bring your friends and come Shake Your Booty with us!

Free
Shake Your Booty 70s Dance Night

Shake Your Booty 70s Dance Night

Vibrissa Beer 10 N. Kent St, WINCHESTER, V, United States

70s BABY!!! 70s music and beyond, 70s attire encouraged but not required. Come for Community, Dinner and Drinks -- Stay to DANCE! (or just come to dance!) Bring your friends and come Shake Your Booty with us!

Free

Trunk or Treat on Loudoun Street

Youth Development Center 302 S Loudoun Street, Winchester, V, United States

๐ŸŽƒ Trunk or Treat on Loudoun Street ๐Ÿ“… Saturday, October 18, 2025 ๐Ÿ•“ 4:00 โ€“ 7:00 PM ๐Ÿ“ 302 S. Loudoun Street, Winchester, VA (YDC Parking Lot) FREE & open to all - thanks to our generous YDC donors! ๐Ÿ‘ป Join us for a spook-tacularย evening of safe, family-friendly Halloween fun right in the heart of […]

Free

HalloWinchester Old Town Merchant Trick r Treat

Loudoun Street Pedestrian Mall

Bring the family to Old Town Winchester for a safe and festive afternoon of trick-or-treating! Local merchants along the Loudoun Street Pedestrian Mall will be handing out candy and goodies to children in costume. Stroll through downtown, show off your Halloween spirit, and enjoy the seasonal decorations, shops, and restaurants that make Old Town such […]

Free

HalloWinchester Pub Crawl

Loudoun Street Pedestrian Mall

Winchesterโ€™s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket โ€” all benefiting Katieโ€™s Comfort House.

$10

Author Event: Dale Watten – Dream Valley Shenandoah

Winchester Book Gallery 7 North Loudoun Street, Winchester, V, United States

Local author Dale Watten has a new book that showcases the native and naturalized flowers of the Shenandoah Valley in Western Virginia. Written in verse, it is accompanied by beautiful […]

First Wednesday Community Information Night

First Wednesday Community Information Night

Bridging the Gaps 31 S. Braddock Street, Winchester, V, United States

Addiction is a struggle โ€” for the person and their loved ones. Thatโ€™s why at Bridging the Gaps, weโ€™re offering ๐…๐ข๐ซ๐ฌ๐ญ ๐–๐ž๐๐ง๐ž๐ฌ๐๐š๐ฒ ๐‚๐จ๐ฆ๐ฆ๐ฎ๐ง๐ข๐ญ๐ฒ ๐€๐๐๐ข๐œ๐ญ๐ข๐จ๐ง ๐ˆ๐ง๐Ÿ๐จ๐ซ๐ฆ๐š๐ญ๐ข๐จ๐ง ๐๐ข๐ ๐ก๐ญ, a ๐Ÿ๐ซ๐ž๐ž ๐ฆ๐จ๐ง๐ญ๐ก๐ฅ๐ฒ ๐ž๐ฏ๐ž๐ง๐ญ […]

Free

Cheesin’ for a Reason – a grilled cheese & tomato soup extravaganza

Winchester Walking Mall Loudoun Street, Winchester, V, United States

Our 1st Annual Grilled Cheese and Tomato Soup Extravaganza for Winchester! ๐Ÿง€๐Ÿ… WATTS will be "Cheesin' for a Reason" this fall and we hope you'll come out and join us in honor of one of our guests' favorite meals. Your ticket includes tastings/samplings of this classic, comfort food combo (with some flair!) from 15+ restaurants […]

$10 โ€“ $20

Community Connections: Strengthening Old Town Together

Winchester Brew Works

We love hearing from our amazing Old Town community! That's why Friends of Old Town is hosting monthly outreach and input sessions all year long. These laid-back, open-forum meetups are a great chance to share ideas, chat about what's happening in Old Town, and help shape our future together. Each session focuses on a fun, […]

First Wednesday Community Information Night

First Wednesday Community Information Night

Bridging the Gaps 31 S. Braddock Street, Winchester, V, United States

Addiction is a struggle โ€” for the person and their loved ones. Thatโ€™s why at Bridging the Gaps, weโ€™re offering ๐…๐ข๐ซ๐ฌ๐ญ ๐–๐ž๐๐ง๐ž๐ฌ๐๐š๐ฒ ๐‚๐จ๐ฆ๐ฆ๐ฎ๐ง๐ข๐ญ๐ฒ ๐€๐๐๐ข๐œ๐ญ๐ข๐จ๐ง ๐ˆ๐ง๐Ÿ๐จ๐ซ๐ฆ๐š๐ญ๐ข๐จ๐ง ๐๐ข๐ ๐ก๐ญ, a ๐Ÿ๐ซ๐ž๐ž ๐ฆ๐จ๐ง๐ญ๐ก๐ฅ๐ฒ ๐ž๐ฏ๐ž๐ง๐ญ […]

Free