Friends of Old Town

First Fridays
2025-10-03 08:00 - 17:00, 2025-09-05 08:00 - 17:00 (America/New_York) | V
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, culture, and small businesses that make Old Town unique. Whether you’re here for special events or just exploring, First Fridays are your invitation to experience all that makes our city a thriving community hub.

Trivia @ DCBC: Emo Music!
2025-10-01 19:30 - 21:30, 2025-10-01 08:00 - 17:00 | Dividing Creek Beer Co, 160 N Loudoun St, Winchester, VA, 22601, United States
Bring your eyeliner and your sadness to our first ever emo trivia. Questions will revolve around all the cool stuff that got you through your most angstiest of times. It was NOT a phase! Prizes to the top three teams. Team sizes limited to 7.

First Wednesday Community Information Night
2025-10-01 17:30 - 19:00 | Bridging the Gaps, 31 S. Braddock Street, Winchester, V, 22601, United States
Addiction is a struggle — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering ????? ????????? ????????? ????????? ??????????? ?????, a ???? ??????? ????? ???? ?? ??? ??????.
This October, attendees will be able to receive Acudetox (ear acupuncture), a technique used in addiction recovery to help reduce cravings, manage stress and anxiety, ease insomnia, and support healing.
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▪️Receive Acudetox treatment from our nurse trained as a NADA Acudetox Specialist
▪️Q&A with our clinicians and admissions team
▪️Practical tools and resources for recovery
▪️Connections to local support and community resources
▪️Light refreshments provided
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? Individuals struggling with addiction
? Family & friends supporting someone in addiction or recovery
? Community members interested in learning more

British Bingo
2025-09-25 18:30 - 20:30, 2025-08-21 18:30 - 20:30 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, 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!

Reggaeton
2025-09-20 21:00 - 23:00 | Bright Box, 15 N Loudoun Street, Winchester, VA, 22601, United States
Join us for the unofficial Winchester Celebración afterparty!
The classics you grew up on. The hits you can’t stop playing. One unforgettable night.
From the golden era of Don Omar, Daddy Yankee, and Ivy Queen to the new wave led by Bad Bunny, Eladio Carrión, Feid, and Karol G— DJ SUELTO and DJ LJ are spinning reggaetón through the ages with a party that blends throwback anthems with the modern Latin sound that’s taking over the world.
Expect nothing but bangers, sweat, and sing-alongs all night long!

Celebracion of Winchester
2025-09-20 12:00 - 16:00 | V
Celebración of Winchester is a free one-day festival celebrating Hispanic Heritage in the Winchester region. It will take place on Saturday, September 20th, from 12 pm to 4 pm in the Old Town Pedestrian Mall in Winchester, and we want YOU to be a part of it!
Stay up-to-date on our Facebook page.

Mabon Luna Market
2025-09-20 10:00 - 17:00 | Moon Phased Metaphysical, 125 S. Loudoun Street, Winchester, V, 22601, United States
Join us for our 3rd annual Mabon Luna Market on Saturday, September 20th from 10 am to 5 pm! We will be hosting 20+ vendors with a large variety of products and services to celebrate the autumn season.

Wine tasting at Murphy Beverage Company
2025-09-19 17:00 - 19:00 | Murphy Beverage Company, 167 N Loudoun Street, Winchester, V, 22601, United States
Come join us for a free wine tasting where Margaret of Williams Corner Wines will pour four wines.

Home Seller Seminar
2025-09-18 17:00 - 19:30 | V
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 selling their homes in today’s market.

EDGE Ensemble Concert
2025-09-17 20:00 - 23:30 | Bright Box, 15 N Loudoun Street, Winchester, VA, 22601, 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.

Open Mic Talent Showcase
2025-09-17 19:00 - 21:00 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, 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 ups start at 6, and the show is on at 7pm. Contact @sargisbrian on Instagram for more information.

Youth Matters: Inspiring the Next Generation of Leaders
2025-09-17 15:00 - 16:00 | 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, guided topic to keep things lively and productive.

Author Event: Sandra Jackson-Opoku - Savvy Summers and the Sweet Potato Crimes
2025-09-14 12:00 - 14:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, 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 of a murder investigation. But when Grandy Jaspers, the 75-year-oldneighborhood womanizer, drops dead at table two, she suddenly has more to worry about than just maintaining Essie’s reputation for the finest soul food in the Chicagoland area.
Even as the police deem Grandy’s death an accident, Savvy quickly finds herself—and her beloved café—in the middle of an entire city’s worth of bad press. Desperate to clear her name and keep her business afloat, Savvy and her snooping assistant manager, Penny Lopés, take it upon themselves to find who really killed Grandy.
But with a slimy investor harassing her to sell her name and business, customers avoiding her sweet potato pie like the plague, and her police sergeant ex-husband suddenly back in the picture, will Savvy be able to clear the café’s name and solve Grandy’s murder before it all falls apart?
Sandra Jackson-Opoku is the author of the award-winning novel, The River Where Blood is Born and Hot Johnny and the Women Who Loved Him, an Essence Magazine Bestseller in Hardcover Fiction. She also coedited the anthology Revise the Psalm: Work Celebrating the Writing of Gwendolyn Brooks. Her fiction, nonfiction, and dramatic works are widely published and produced in Adi Magazine, Midnight & Indigo, Aunt Chloe, Africa Risen: A New Era of Speculative Fiction, New Daughters of Africa, Obsidian, Another Chicago Magazine, story South, Lifeline Theatre, the Chicago Humanities Festival, and others. Professional recognition includes a Plentitudes Journal Prize, the Hearst Foundation James Baldwin Fellowship at MacDowell Arts, a National Endowment for the Arts Fiction Fellowship, an American Library Association Black Caucus Award, a City of Chicago Esteemed Artist Award, the Iceland Writers Retreat Alumni Award, a Globe Soup Story Award, the Joan Perry Barnes Fellow in Crime Writing at Story knife Writers Retreat and a Pushcart Prize nomination.

Fiddles & Fifths - Bluegrass & Bourbon Festival's
2025-09-13 13:00 - 19:00 | V
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 on sale soon!
Save the date, tell your friends, and come party with us in the heart of Old Town

Author Event: Leah Rampy - Earth & Soul
2025-09-13 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, 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 reconnect with Earth. As we follow the author’s compelling personal experiences and engagingly lyrical stories of whales, cedars, sparrows, and more, we see the necessity and urgency of learning from the wisdom of our kin in the natural world. Writing at the intersection of spirituality, ecology, and story, Leah Rampy illuminates a path to reweaving nature and soul. Under Rampy’s deft guidance, the beauty and genius of this sacred world unfolds before us. Even now when the world as we knew it is ending and a new story lies beyond what we can envision, we may live fully alive and lay stepping stones toward a diverse and vibrant world of oneness and mutual flourishing.

ShenArtsFest
2025-09-06 10:00 - 18:00 | V
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 and Indian Alley, visitors will have the opportunity to discover handmade-in-the-USA, original works of art across every medium, along with music, dance and various entertainers.​
ShenArts’ careful vetting process ensures the finest and most diverse offerings of sculpture, pottery, jewelry, photography, mixed-media, painting and more to suit every artistic taste and budget.
** ShenArts Fest will take place rain or shine.

Anniversary Weekend British Bingo!
2025-08-31 18:00 - 20:00 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, United States
It’s The Cider House’s one year anniversary on Labor Day Weekend! We’re celebrating with British Bingo!

15th Annual Patsy Cline Block Party
2025-08-30 10:00 - 16:00 | Patsy Cline Historic House, 608 South Kent Street, Winchester, V, 22601, 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 include live music, specially priced tours, food vendors, Patsy Cline Merchandise, and our 3rd Annual Hungry For History Food Event, featuring Patsy’s Specialty Soda Drinks! Notably, no alcohol is permitted at the event. Parking will be limited around the block party itself; however, visitors can park and ride for free at the Winchester-Frederick County Visitor Center (1400 S. Pleasant Valley Rd), where the Trolley will be continuously running throughout the day at no charge. We hope to see you there!

Open Mic Talent Showcase
2025-08-28 19:00 - 21:00 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, 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 at 7pm. Contact @sargisbrian on Instagram for more information.

Karaoke with DJ Blue Nova
2025-08-27 19:00 - 21:00, 2025-08-13 19:00 - 21:00 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, 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 notes, worst fears, and bravest friends… because it’s time to sing your heart out (or at least try).

Trivia at 50/50 Taphouse
2025-08-21 20:30 - 22:00 | 50/50 Taphouse, 29 West Cork Street, Winchester, Virginia, 22601
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 hosted and organized by Eric McBride.
Prizes are $25 off the 1st place team’s tab; $15 off of the 2nd place team’s tab. There is no fee to play.

Celebrating the Seasons: Holiday Events in Old Town
2025-08-20 15:00 - 16:00 | Winchester Brew Works

Author Event: Bryan Lienesch - Happyland
2025-08-16 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Stop by the Book Gallery to meet thriller author B. C. Lienesch and celebrate his latest publication! Dive back into the world of Jackson Clay with brand new mysteries and the self-same darkness we’ve come to expect from his adventures.
See you there!

One Haute Summer Night
2025-08-14 19:00 - 21:00 | The Cider House, 30 E Piccadilly St, Winchester, V, 22601, United States
Welcome to One Haute Summer Night, a drag show at The Cider House! Get ready for a fabulous night filled with dazzling performances and non-stop entertainment. Join us on August 14, 2025 for a show you won’t forget. Doors at 6pm and show at 7! Come and experience the magic of drag in person! Don’t miss out on this unforgettable evening. Tickets are $15 in advance or $20 at the door. See you there!

Author Event: Steven O'Farrell - Simone LaFray Mysteries
2025-08-09 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Stop by the Winchester Book Gallery to meet Steve O’Farrell and take home a signed copy of his newest middle grade mystery! Simone LaFray is a globetrotting investigator – join her on her latest case!

Author Event: Nicole Hanlin – Unlock the Power of Potential
2025-08-02 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Author Nicole Hanlin will join us this Saturday for a signing of her newest publication! Stop by to learn more about her latest work in self-investment and career development, and to Unlock Your Potential!
