British Bingo

British Bingo

The Cider House 30 E Piccadilly St, Winchester, V, United States

British Bingo is going monthly! 🎉 Join us for British Bingo every third Thursday of the month at The Cider House! Hosted by our very own cidermaster, it’s totally free to play, with prizes, cider, and fun guaranteed. Mark your calendars, bring your mates, and let the games begin!

Free
Trivia at 50/50 Taphouse

Trivia at 50/50 Taphouse

50/50 Taphouse 29 West Cork Street, Winchester, Virginia

Come out to 50/50 Taphouse in Winchester, Virginia every Thursday (except holidays) to play general trivia with all of your friends. Get your team together or challenge yourself. Trivia is […]

Karaoke with DJ Blue Nova

Karaoke with DJ Blue Nova

The Cider House 30 E Piccadilly St, Winchester, V, United States

🎤 Karaoke Nights are coming to The Cider House! 🎵 Starting Wednesday, August 13, we’re teaming up with DJ Blue Nova for karaoke every other Wednesday night! Bring your best […]

Free

Open Mic Talent Showcase

The Cider House 30 E Piccadilly St, Winchester, V, United States

Have you got talent? Want to try your hand in front of a live crowd? The Cider House is having an Open Mic Showcase August 28! Unlike most open mics, this one isn't for music. We will be featuring comedy, magic, monologues... you name it! Sign ups start at 6, and the show is on […]

Free

15th Annual Patsy Cline Block Party

Patsy Cline Historic House 608 South Kent Street, Winchester, V, United States

Join us in celebrating Patsy Cline's Birthday and contribution to American Culture at our 15th Annual Patsy Cline Block Party on August 30th, 2025, between 10 am and 4 pm. This free community event is hosted by the Patsy Cline Historic House and will be staged at the 600 Block of South Kent Street. Events […]

Free

Anniversary Weekend British Bingo!

The Cider House 30 E Piccadilly St, Winchester, V, United States

It's The Cider House's one year anniversary on Labor Day Weekend! We're celebrating with British Bingo!

Free

First Fridays

First Fridays

Discover the heartbeat of Old Town Winchester with Friends of Old Town’s First Fridays! From June through October, kick off your weekend each month with live music, local art, and the popular sip & stroll program, which lets you enjoy our vibrant downtown while supporting Old Town’s restaurants and shops. These evenings celebrate the creativity, […]

ShenArtsFest

Old Town Winchester, VA is a beautiful venue for a festival with dedicated crowds and wonderful staff and volunteers. We hope you will apply!​ The Shenandoah Arts Council (ShenArts) is proud to present a juried, fine art festival, showcasing the work of artists from all over our region. Located along Piccadilly St. between Cameron St […]

Free

Author Event: Leah Rampy – Earth & Soul

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

Amidst accelerating climate devastation and an uncertain future comes a clarion call to renew a deep and personal relationship with Earth. Facing directly into the devastation of climate chaos and biodiversity loss, Rampy leads her readers on a soul journey into grief and loss to also claim the beauty, joy and possibilities available when we […]

Fiddles & Fifths – Bluegrass & Bourbon Festival’s

Join us at the Old Civil War Museum in downtown Winchester for a free day of live music, local flavor, and bourbon tastings. 🎶 Featuring performances by: 🔥 The Bridge City Sinners 🎸 Brennan Edwards & The Monday Blues 🎻 Reno & Dunlap Music kicks off at 2 PM, and bourbon tasting tickets will be […]

Free

Author Event: Sandra Jackson-Opoku – Savvy Summers and the Sweet Potato Crimes

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

With SAVVY SUMMERS AND THE SWEET POTATOCRIMES award-winning author Sandra Jackson-Opoku presents a sparkling debut mystery set on the south side of Chicago, featuring the quick-witted, unforgettable Savvy Summers, proprietor of a soul food café. When Savvy first opened Essie’s soul food café, she never expected her customer-favorite sweet potato pie to become the center […]

Youth Matters: Inspiring the Next Generation of Leaders

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, […]