Trunk or Treat on Loudoun Street

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

🎃 Trunk or Treat on Loudoun Street 📅 Saturday, October 18, 2025 🕓 4:00 – 7:00 PM 📍 302 S. Loudoun Street, Winchester, VA (YDC Parking Lot) FREE & open […]

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 […]

Free

HalloWinchester Pub Crawl

Loudoun Street Pedestrian Mall

Winchester’s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket — all benefiting Katie’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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

Free

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 […]

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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

Free

Year in Review: Reflecting on Old Town’s Growth

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 […]

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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

Free

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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

Free

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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

Free