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, […]

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 September 17! Unlike most open mics, this one isn't just for music (honestly, we only have the vibe/hookups for acoustic). We will be featuring comedy, magic, monologues... you name it! Sign […]

Free

EDGE Ensemble Concert

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

Shenandoah New Music Passport Control Celebrate Shenandoah University’s sesquicentennial with the EDGE Ensemble as it looks boldly to the future, celebrating the next 150 years of music on planet Earth. This vibrant program features new works by living composers from Australia, France, Iceland, Poland, Slovenia, Sweden and the United States.

$15

Home Seller Seminar

Thursday, September 18th from 5:00–7:30 PM at the Handley Library (Benham Gallery Room) here in Winchester. This free community event will give local homeowners practical tips on preparing, pricing, and […]

Free

Wine tasting at Murphy Beverage Company

Murphy Beverage Company 167 N Loudoun Street, Winchester, V, United States

Come join us for a free wine tasting where Margaret of Williams Corner Wines will pour four wines.

Free