Friends of Old Town

Spin to Win-chester
2026-02-21 13:00 - 15:00 (America/New_York) | Valley Health Fitness Center, 401 Campus Blvd, Winchester, V, 22601, United States
Spin to Win-Chester ?‍♂️?
Think you’ve got what it takes? Spin to Win-Chester is a high-energy spin-a-thon where riders compete, fundraise, and push themselves—all in support of Old Town Winchester. Join us Saturday, February 21 at Valley Health Wellness & Fitness Center for a Winchester-themed ride led by Pam Lambert.
Choose Your Challenge

Beginner Ride: 35 minutes | 1:00–1:35 PM
Perfect for first-time riders ready to jump in and compete
Intermediate Ride: 30 minutes | 2:00–2:30 PM
Faster, tougher, and built for riders looking to level up

The Competition

$250 minimum to ride (fundraise or pay to enter)
Prizes awarded for top fundraisers and standout riders
Rain or shine event
All proceeds benefit Friends of Old Town
Not riding? Donate and back your favorite competiton

Why It Matters
Friends of Old Town is dedicated to fostering a vibrant, inclusive, and economically thriving Old Town Winchester. Through public art, historic preservation, and community-driven initiatives, we celebrate what makes Old Town unique while investing in its future. As stewards of the Virginia Main Street program, we work to create a welcoming place for residents, businesses, and visitors alike.

Author Event: Greg Kujala - Working at Love
2026-02-21 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Working at Love continues the story of Amanda and David following their graduation from Jefferson Medical College. Amanda chose a residency in pathology at Jefferson, while David opted for psychiatry at the Brigham in Boston. Their long-distance connection over the course of the next five years was difficult to maintain. Both Amanda and David grew in affection and respect for each other despite the time and miles between them. Their story opens after they experience a bump in the road during their relationship.

Author Event: James Blakey - Shenandoah Fantastic
2026-02-22 12:00 - 14:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Get the latest from local author James Blakey, SHENANDOAH FANTASTIC, and experience the Valley like never before!
Time travelers at the Shakespeare Center…Space aliens at Route 11 Potato Chips…Trolls beneath Luray Caverns…
Twenty-four stories of fantasy, horror, and science fiction in all.

Celebrating Black History Month: History & Cocktails
2026-02-26 18:00 - 19:30 | Bright Box, 15 N Loudoun Street, Winchester, VA, 22601, United States
Join us for a meaningful and memorable evening as we celebrate Black History Month with History & Cocktails Night at Bright Box Theater.
This relaxed, intimate event will feature short talks and local storytellers sharing stories that highlight Black history in Winchester and the surrounding region. It’s a chance to connect with our community’s past in a welcoming, engaging setting — all while enjoying a night out in Old Town.
Whether you come for the history, the conversation, or the cocktails, this evening is designed to bring people together through storytelling, reflection, and community.
February 26 6:00–7:30 PM Bright Box Theater (Upstairs)
Come early, grab a drink, and settle in for a night that honors the stories that shape our community.
Presented as part of Black History Month in Old Town, with generous support from Valley Health.

Finding Your Revolutionary War Hero
2026-03-01 - 2026-03-31 | V
The Fort Loudoun DAR chapter is sponsoring an event akin to “Where’s Waldo” where participants get a Passport and go to the 38 participating merchants in Old Town to locate each Rev War Hero. Once they get 10 they can go to the Winchester Frederick Co. Visitor Center for a prize.

FREE Midday at The YDC!
2026-03-03 10:00 - 13:00, 2026-04-07 10:00 - 13:00 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
Midday at The YDC is a relaxed, inclusive daytime program designed to give families a place to connect, learn, and spend meaningful time together. Open to all school-aged children and their caregivers, this drop-in experience invites families to use The YDC as a community space that supports curiosity, creativity, and connection.
During Midday at The YDC, families have access to our reading rooms, art supplies, game room, and esports room, allowing children of mixed ages to explore interests at their own pace. Parents and caregivers are required to remain with their children at all times, making this a shared experience that encourages engagement and community building.
This program takes place on Tuesdays and Thursdays from 10:00 AM to 1:00 PM and is open to all families, whether you homeschool, have a day off from school, or are simply looking for a welcoming place to spend part of your day. The cost is $5 per day per family, and the first Tuesday of each month is free. Families are encouraged to bring snacks and drinks and enjoy the space in a way that works best for them.
Midday at The YDC creates room in the day for learning, creativity, and belonging, right in the heart of our community.

First Wednesday Community Information Night
2026-03-04 17:30 - 19:00, 2026-04-01 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

Sip & Start
2026-03-06 18:00 - 20:00 | Winchester Brew Works
Together, we’ll enjoy drinks ? and more from WBW while we start tomato ? plants for your summer garden or container garden with guidance & supplies ? ? from Moon Base Farms. Beginners, experts and everybody in the middle are all invited. You don’t need to know ANYTHING about gardening, we’ve got you covered!
Supplies provided in a limited capacity per family/person and there is a suggested $5 donation in cash or card, which we will donate 100% of directly to CCAP (neighbors helping neighbors with food, money and more!).
If you attend and participate, you will leave with:
– A tomato plant or two of your own and instructions for how to not unalive them. We believe in you!
– Delicious refreshments from Brew Works
– A unique discount code for our farms online store to use on produce
– Connections to other gardeners in Winchester & good vibes
– Answers to questions about gardening, farming and related topics.
FAQ:
– Does it cost anything? No, but there is a suggested donation of $5 which 100% will be given to benefit CCAP. The more we raise, the more we help our neighbors in need.
– I have my own seeds and supplies, could I bring them? Yes, you may bring your own supplies (keep it small and consider the venue).
– Will it be family friendly? Adults, and adults with kids are all welcome. If you bring family, please participate with your kids.
– Will I have help if I don’t know what I’m doing? Yes!
– I don’t know where I’ll put the plant. We can chat through and help you choose the best spot!
– What is a Moon Base Farms? We’re a farm in Winchester, nice to meet ya!
See you there and tell your pals!

Author Event: Anne Marchant - Wild Virginia
2026-03-14 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
A Virginia wildlife conservation officer and a wildlife veterinarian team up to save animals from poachers and traffickers. With the support of colleagues, they rehabilitate sick and injured animals so they can be released. Along the way they engage in several search and rescue operations and solve a case of attempted murder. Dedication to their work leaves no time for romance, or does it? Stop by to grab your signed copy of Marchant’s newest work!

Celtic Fest
2026-03-14 12:00 - 17:00 | Loudoun Street Pedestrian Mall
Hark and gather, ye merry souls!
On Saturday, March 14th, Old Town shall be awash in music, mirth, and Celtic cheer as we proclaim a grand celebration — Celtic Fest!
From the twelfth hour ‘til five of the clock, the Walking Mall shall be transformed into a lively festival village. Those who wander through shall discover:
Lively tunes from pipers and roaming musicians A splendid market of vendors, brought forth in partnership with the fine folk of Ravenwood, offering wares most curious and delightful Hearty food and drink to fortify thy festival spirit Dancing, laughter, and jolly fellowship in the open air
Don thy greenest raiment, gather thy friends and kin, and roam the ancient brick pathways as song fills the breeze and the spirit of the Celts takes hold.
Yet hold fast — for when the sun dips low, the revelry doth not end…
At the seventh hour of the evening, the Celtic Bar Crawl begins! Brave adventurers shall embark upon a noble quest from tavern to tavern, raising glasses, sharing cheers, and keeping the merriment alive well into the night.
So make haste and mark thy calendars — a day of music, magic, and memory awaits in Old Town. Thou art most warmly summoned to the festivities!

Author Event: Mari-Jo Qualey - Soul Evidence
2026-03-28 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
What makes us who we are? When a lethal wave of unexplained comas sweeps across the globe, brain specialist Dr.Isabelle Beckinsale and her team race against time to save humanity—includingher own twin sister. Their discovery that every coma patient’s brain wavesmatch those from a distant star cluster launches them on a mission to thedepths of space, where Isabelle must attempt the unthinkable to prevent humanextinction. Part medical thriller, all sci-fi – grab yours today!

Spring Sale At Kimberly's, McKee's, and The Market
2026-04-01 - 2026-04-15 | Kimberly’s, 135 N Braddock St, Winchester, VA, 22601, United States
20% off at Kimberly’s, McKees, and The Market
Some exclusions apply.*

Author Event: Linda Ruth Lee - Way Beyond
2026-04-04 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
With unflinching honesty and emotional depth, Linda Ruth Lee invites readers into her journey through shame, secrecy, and resilience. As a fifteen year old teenager facing an unexpected pregnancy in an unforgiving era, Linda makes a life-altering decision—one that reverberates through her family for years to come. But this is not just a story of loss or regret. It’s a testament to the power of love, forgiveness, and the incredible ways life can be fulfilling.

Author Event: Jason Bucklew - Helixandra
2026-04-04 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
A fast-paced survival thriller about a group stranded on a hidden island filled with prehistoric creatures, dark secrets, and a mastermind pulling the strings. Survival isn’t guaranteed-and escape may come at a deadly cost. Please welcome Jason to the shop and grab a signed copy of his book!

ReadStart with Rowan
2026-04-07 16:00 - 17:00, 2026-04-09 16:00 - 17:00, 2026-04-13 16:00 - 17:00 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
ReadStart is a twice-weekly literacy program that provides young learners with a strong foundation in early reading skills, combined with individualized tutoring support. Designed for children ages 7-12 who may need additional help in fluency, vocabulary, and comprehension, this program aims to boost reading confidence, close literacy gaps, and foster a lifelong love of reading.
The program integrates evidence-based literacy instruction, small group work, and one-on-one support to meet each child at their current level and help them grow.

Shenandoah Valley Indie Bookshop Crawl 2026
2026-04-11 - 2026-04-24 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
This two-week celebration (April 10 – 25, 2026) brings book lovers together across the region, reminding us how much joy there is in gathering around books and in showing up for the independent shops that bring them to us.
Every participant may enter one store-specific drawing for a $50 prize from the participating bookshop of their choice. Simply check the box for your favorite shop on your passport.
Visit 7 or more participating bookshops and collect 7+ stamps or stickers to enter the grand prize drawing for a $25 gift card from each participating store, worth $225 total.
With 7 or more stops, you can enter both a store-specific prize and the grand prize.

Author Event: Harmony Joy - Dark Nights of the Soul
2026-04-11 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Centered around four emergency hospitalizations for “behavioral health” over the course of eight years, Dark Nights of The Soul newly honors the turmoil of trying times -while supplementing them with the greater perspective that comes with growth and reflection. Ultimately, it navigates a journey from seemingly impossible pain and fear, doubt and darkness into abundant healing and hope, faith and light.
Join us for Harmony Lee’s event this Saturday!

Author Event: Brian Gilmore - No More Worlds to Conquer
2026-04-11 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
More than a historical account, No More Worlds to Conquer is a personal exploration that bridges the past and the present. Gilmore, who was born and raised in DC, illuminates this history and reflects on his own place in its literary tradition. This multigenerational account will resonate with poetry enthusiasts, local DC scholars, and anyone interested in the rich traditions of African American literature.

Author Event: Greg Kujala - Fifty Artists of the Shenandoah Valley
2026-04-12 12:00 - 14:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
This first Volume of Artists of the Shenandoah Valleyprovides an in-depth look at the most talented creatives working out of theShenandoah Valley in Virginia and West Virginia. An often overlooked group ofartists, this collection presents a vibrant and multifaceted selection of theart world, showcasing inspiration and ideas from across the big valley.

Author Event: Jeff Bennett - The Black Belt of Virginia: Untold Stories of African American History
2026-04-18 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
See the history of more than seventy Black communities lost in Virginia. Read the story of a 135-year-old church and the meaning behind land passed down through generations. These stories show the strength and impact of Black families before and after slavery. Perfect for history lovers and older readers, this collection brings forgotten voices back to life.

Author Event: Joshua Putnam - A Heavy Metal History Lesson
2026-04-18 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
A Heavy Metal History Lesson is the world’s first collection of stories that delve into the historical events and figures that inspired ten different heavy metal songs. Art has long served as a vessel for history—whether through poetry, musicals, literature, or film—presenting world history to the masses, with varying degrees of accuracy. A Heavy Metal History Lesson aims to educate headbangers about world history and the events that inspired some of their favorite tracks!

Independent Bookstore Day 2026
2026-04-25 | V
JOIN US FOR THE 13TH ANNUAL INDEPENDENT BOOKSTORE DAY!
This national one-day party held the last Saturday in April celebrates independent bookstores across the country online and in-store. Through exclusive books and literary items, celebrations, and everything in between, it’s a book party you don’t want to miss!

Independent Bookstore Day 2026
2026-04-25 | V
The Winchester Book Gallery is delighted to be celebrating the 13th Independent Bookstore Day! We will be open 9 am to 9 pm with fun for everyone! There will be snacks and book fun all day long! Please stop in: play and shop with us!

NOVA+ Bookstore Crawl
2026-04-25 - 2026-05-31 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Celebrate Independent Bookstore Day and kick off a month-long literary adventure with the 2026 Bookstore Crawl! Beginning April 25, swing by any participating indie bookstore to pick up your official printed passport, then start exploring throughout the month of May.

Greener Living Day at The YDC!
2026-04-25 11:00 - 16:00 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
Greener Living Day is a free, community-centered sustainability event hosted by The YDC, designed to inspire environmentally conscious living through education, hands-on experiences, and local connection. This free event brings together families, community members, and local organizations for a day focused on learning, growing, and working toward a greener future.
Throughout the day, attendees can explore interactive planting and horticulture stations, learn practical sustainability tips from guest speakers, and connect with local businesses and organizations committed to environmental stewardship. Participants will have the opportunity to plant something of their own, either to take home or to contribute to The YDC’s growing community garden, a youth-led initiative that will continue beyond the event.
Greener Living Day also features live music, art, and ongoing activities that make sustainability accessible, engaging, and fun for all ages. With presentations on plant care, greener living practices, and the value of sustainability in everyday life, the event offers meaningful takeaways while celebrating community collaboration.
At its heart, Greener Living Day is about bringing people together, strengthening local partnerships, and empowering youth and families to play an active role in caring for the world around them. We invite the community to join us for a day of learning, connection, and shared responsibility as we grow something lasting together.
LIVE PERFORMANCE BY: The 5th Mode Collective
Confirmed Community Partners:
Moon Base Farm
Michael Recycle
Hillary Sortor
The Nature Journaling Club
WinReady
Jordan Herring, The Native Plant Festival
Bee City USA
Northern Shenandoah Valley Extension Master Gardener Association
WSPCA
Julia Carter and Carie Holbrook, Public Services
Sustainability Matters
Publisher Holistic Living Now
The Station Mobile Cafe
Apple Hill Farm

Author Event: Will Hackman - Radically Reframing Climate Change: A Guide to Saving Ourselves
2026-04-25 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Author Will Hackman identifies three main obstacles to solving climate change: polarization, paralysis, and stale, ineffective messaging. He empowers readers to turn their anxiety or apathy into passion, and anger into action at the personal, community, and government levels. Come celebrate Apple Blossom, Independent Bookstore Day, and Will Hackman’s new release! He will be here to sign books, answer questions about his book, and chat about anything climate related.
