Friends of Old Town

HalloWinchester Pub Crawl
2025-10-25 18:00 - 23:00 (America/New_York) | 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.

HalloWinchester Old Town Merchant Trick r Treat
2025-10-25 14:00 - 16:00 | 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 a special place.
This free community event is open to kids of all ages—costumes encouraged!

Trunk or Treat on Loudoun Street
2025-10-18 18:00 - 20:30 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, 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 to all – thanks to our generous YDC donors!
👻 Join us for a spook-tacular evening of safe, family-friendly Halloween fun right in the heart of downtown Winchester!
What to Expect:
30+ decorated trunks with candy giveaways 🎃🍬
Haunted house walkthrough inside YDC 👀
Music, costumes & fun photo ops
Community organizations, public safety partners & volunteers
Prizes for best-decorated trunks!
Costumes encouraged!
🍔 Food truck TBA for dinner and treats.
👨‍👩‍👧‍👦 All ages welcome and costumes are encouraged!
♿ ADA accessible | Restrooms available inside
📝 Free registration encouraged — walk-ups welcome!

Shake Your Booty 70s Dance Night
2025-10-16 19:00 - 22:00, 2025-10-16 08:00 - 17:00 | Vibrissa Beer, 10 N. Kent St, WINCHESTER, V, 22601, 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!

Catalyst Quartet
2025-10-15 20:00 - 23:30 | Bright Box, 15 N Loudoun Street, Winchester, VA, 22601, United States
Shenandoah New Music
Hailed by The New York Times as “invariably energetic and finely burnished,” 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 dynamic program features works by some of today’s most compelling living composers — including Jessie Montgomery, Kevin Puts and Caroline Shaw, among others — culminating in a rare performance of CQminute, a powerful collection of commissioned miniatures celebrating the quartet’s first ten years together.

Tech-Forward Town: Digital Tools for a Connected Community
2025-10-15 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.

Fall Vendor Pop-Up Market
2025-10-12 13:00 - 15:00 | Vibrissa Beer, 10 N. Kent St, WINCHESTER, V, 22601, United States
Join us Sunday, October 12th from 1-3pm, rain or shine, to support some local small business at your hometown brewery!
🍻🛍️Beer & shopping?! who knew those were such a good idea together!!!
Vendors:
Cici’s Permanent Jewelry Bar
Lost in the Stitch
Southern Belle Creations
Sipsy’s
T’s Glitter & Grace
Country & the Geek
Creations of Genesis
The Hippie Willow
Just Darlin’ Jewelry
Meadow & Moss
Crouse Creations
The Hat Bar
This event is being held at our WINCHESTER location located at 10 N Kent Street, Winchester, VA 22601

Beer and Halloween Candy Pairing at Murphy Beverage Company
2025-10-11 14:00 - 16:00 | Murphy Beverage Company, 167 N Loudoun Street, Winchester, V, 22601, United States
We’ll be pouring samples of beer paired with candy to help you get ready for Halloween. Sponsored by Taryn Obssuth, realtor at Keller Williams, and Kate A. Walker of Integrity Home Mortgage.

Savor the World
2025-10-09 17:30 - 19:30 | Godfrey Miller Center, 28 South Loudoun Street, Winchester, V, 22601, United States
A memorable evening of fine wine, connection, and culinary delight—all in support of a meaningful cause.
Explore international wine and food pairings in a progressive tasting experience. The night culminates with a lively Wine Pull, where every ticket gets a bottle of wine.

The Magic Flute ballet
2025-10-05 14:00 - 15:30, 2025-10-04 17:00 - 18:30, 2025-10-04 14:00 - 15:30 | Vostrikov’s Academy of Ballet, 20 West Cork Street, Winchester, V, 22601, United States
Virginia Youth Ballet presents a classic ballet, The Magic Flute.
Let the Magic of Kindness and Love Enchant You
Step into a world where music holds the power to change destinies and love conquers all obstacles. In a charming village shadowed by struggle and longing, a humble boy’s act of generosity awakens the magic of a flute, unlocking hope, healing, and joy for everyone. As friendship blooms into love and hearts are mended, witness how a single melody can transform sorrow into celebration. The Magic Flute ballet invites you to experience an unforgettable tale where kindness is the greatest enchantment of all. Don’t miss this radiant story—where every note is a promise of happiness!
Please arrive 15 minutes prior to the start of the performance. The performance will last approximately 1 1/2 hours.
**Flowers for purchase for dancers; Vostrikov’s/VYB merchandise, and Concession will be available during intermission**

Banned Books Week
2025-10-05 - 2025-10-11 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
The American Library Association and Banned Books Week Coalition are pleased to announce the theme for Banned Books Week 2025: “Censorship Is So 1984. Read for Your Rights.” Banned Books Week will take place October 5 – 11, 2025. As always, we will be celebrating Banned Books Week with a huge table of banned books from the classics to books banned in more recent years. Come down to the shop to celebrate our right to read by picking up a banned book!

Author Event: Beka Wueste - Fireflies in a Jar
2025-10-04 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Come down to the shop to celebrate Beka Wueste’s sophomore novel, “Fireflies in a Jar,” a mid-life coming of age story for anyone who has ever felt like they don’t fit in, don’t have everything figured out, or haven’t hit the milestones expected of them. Beka will be here to sign copies and talk about her new release!

Author Event: Leenie Hobbie - Elder Legacies
2025-10-04 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Can two young women rely on their traditional herbal knowledge and skills to make their way in a world constructed by and for men? Amid world war and rampant disease, they discover they must also catch a murderer. Come meet first time local author Leenie Hobbie and get your signed copy.

Thrift on Tap at Dividing Creek!
2025-10-03 12:00 - 19:00 | Dividing Creek Beer Co, 160 N Loudoun St, Winchester, VA, 22601, United States
Sip, shop, and score big at our one of a kind thrift event! 🍻🛍️
We’re bringing together a few of the best local thrifters, vintage curators, and small shops for a day of treasures, bargains, and brews. Wander through racks of unique finds, sip on craft beer, and discover your next favorite outfit or home good- all while supporting sustainability & local businesses.
Whether you’re hunting for vintage gems, affordable fashion, or just a fun day out, Thrift on Tap has you covered. Come thirsty!
More info: https://partiful.com/e/qu6TofpfYbyLwy50P6E6

First Fridays
2025-10-03 08:00 - 17:00 | 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 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 𝐨𝐩𝐞𝐧 𝐭𝐨 𝐭𝐡𝐞 𝐩𝐮𝐛𝐥𝐢𝐜.
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.
𝐖𝐡𝐚𝐭 𝐭𝐨 𝐄𝐱𝐩𝐞𝐜𝐭:
▪️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
𝐖𝐡𝐨 𝐒𝐡𝐨𝐮𝐥𝐝 𝐀𝐭𝐭𝐞𝐧𝐝:
💜 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 | 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
