Friends of Old Town

Summer Art Class
2026-07-22 10:30 - 11:30, 2026-07-15 10:30 - 11:30, 2026-07-08 10:30 - 11:30, 2026-07-01 10:30 - 11:30, 2026-06-24 10:30 - 11:30, 2026-06-17 10:30 - 11:30, 2026-06-10 10:30 - 11:30, 2026-06-03 10:30 - 11:30 (America/New_York) | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
Our Summer Art Series at the YDC is a fun, creative opportunity for kids to explore, learn, and express themselves in a welcoming environment.
Made possible by the generosity of our donors, this program is offered free of charge to families in our community.
Each week features a new project designed to inspire creativity, build confidence, and encourage self-expression. Ms. Lindsay will be back leading the series, joined by a few special helpers along the way to bring fresh ideas and energy to each session.
This program is best suited for ages 6–12, however we’re happy to work with families. If you have a child outside of that age range who is interested, please don’t hesitate to reach out.
We look forward to creating with you this summer!
Please contact ad***@***dc.org with any questions!

The All-American Pig & Pour
2026-07-18 15:00 - 21:00 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
Presented by Heaven Hill Distillery and Partlow Insurance, the All-American Pig & Pour returns to the YDC on Saturday, July 18 for one of Winchester’s favorite summer traditions.
Blending upscale Americana charm with the energy of a summer backyard gathering, the All-American Pig & Pour brings the community together for an evening filled with bourbon, barbecue, live music, cigars, games, community bartenders, and meaningful support for the YDC and the families we serve.
Guests can expect a whole hog roast, bourbon tastings, live entertainment, silent auction opportunities, raffles, a 50/50 drawing, and additional ways to support YDC programming throughout the evening. Community bartenders from local businesses and restaurants will help give the event a true hometown feel while guests enjoy food, cocktails, music, and summer celebration in downtown Winchester.
General Admission begins at 4PM and tickets are $40, including food, two drinks, and one raffle ticket.
VIP access begins at 3PM and includes a private bourbon tasting experience inside one of the YDC property’s most unique and historic spaces. The tasting will take place inside the building’s historic prison room, a barrel-vaulted stone space connected to Winchester’s Revolutionary War history. Preservation of Historic Winchester notes there is strong historical belief that Hessian prisoners of war captured during the Revolutionary War were once held within the space, making it one of the most distinctive event experiences in the region.
The All-American Pig & Pour is more than a summer event. It is an opportunity to invest directly in programs that help young people and families succeed through the YDC, including free arts programming, literacy initiatives, scholarships, enrichment opportunities, and community-centered experiences throughout the year.
This event is open to guests ages 18 and older. Guests must be 21+ to consume alcohol.

Monty Python Pub Crawl
2026-07-17 18:00 - 21:00 | Loudoun Street Pedestrian Mall
🏰 HEAR YE, HEAR YE, brave souls of the Shenandoah Valley! ⚔️
The Holy Grail has been hidden somewhere in Old Town Winchester… and we need a fellowship worthy of the quest.
🗓️ Friday, July 17, 2026
📍 Old Town Winchester, VA
🍺 A Monty Python Pub Crawl: A Quest for the Holy Grail
Follow the clues. Hit the best spots in Old Town. Claim glory for FIVE worthy causes – AIDS Response Effort, Inc. (ARE), Blue Ridge Care, Ccap Winchester, Friends of Old Town right here in our community.
Costumes are strongly encouraged. Coconuts are optional (but you know you want to). Killer rabbits are… probably not included.
None shall pass on this one, friends. Gather thy knights, thy squires, thy shrubberies — and grab thy tickets before they vanish faster than the Black Knight’s arm.
🎟️ Get thy tickets: UnitedWayNSV.org/MPPC

Author Event: Andrew Lawlor - A Perfect Frenzy
2026-07-11 14:00 - 16:00 | Handley Regional Library, 100 W. Piccadilly Street, Winchester, VA, 22601, United States
Andrew Lawlor, author of A Perfect Frenzy: A Royal Governor,His Black Allies, and the Crisis That Spurred the American Revolution willbe speaking at the library on July 11 from 2 pm to about 4pm.

VA250 Old Town Jubilee
2026-07-04 12:00 - 22:00 | Loudoun Street Pedestrian Mall
Celebrate 250 years of history, community, and Virginia pride at the Old Town Jubilee! Enjoy a full day of local vendors, food, family-friendly activities, and live entertainment throughout historic Old Town.
Gather at the Taylor Pavilion for live performances by Rebecca Porter and Melissa and the Mothmen, then cap off the evening with a spectacular Laser Light Show on the Civil War Museum Lawn.
Join friends, neighbors, and visitors as we honor Virginia’s 250-year legacy with music, celebration, and unforgettable experiences for all ages. Celebrate 250 years with us!

First Friday
2026-07-03 17:00 - 21:00, 2026-06-05 17:00 - 21:00 | Winchester Downtown Walking Mall, Winchester, V, 22601, United States
Friday nights are back in Old Town Winchester.
Join Friends of Old Town for First Fridays, a monthly community celebration bringing live music, local artists, vendors, pop-ups, food, shopping, and extended downtown energy to the Walking Mall throughout the summer and fall.
Each First Friday features:

Live music at Taylor Pavilion
Local artists and makers
Vendors throughout the Walking Mall
Specials and extended hours from downtown businesses
Family-friendly activities
DORA drinks throughout Old Town

Whether you’re grabbing dinner, shopping local, meeting friends for drinks, or just wandering downtown, First Fridays are all about giving people another reason to stay a little longer and experience everything Old Town has to offer.
2026 First Friday Dates:

June 5
July 3
August 7
September 4
October 2

Event runs from 5–10 PM.
Music and programming may vary each month.
Presented by Friends of Old Town and sponsored by First Bank.

First Wednesday Community Information Night
2026-07-01 17:30 - 19:00, 2026-06-03 17:30 - 19:00 | Bridging the Gaps, 31 S. Braddock Street, Winchester, V, 22601, United States
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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
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▪️Light refreshments provided
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? Individuals struggling with addiction
? Family & friends supporting someone in addiction or recovery
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Find Waldo Local Begins!
2026-07-01 10:00 - 2026-07-31 19:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
It’s time for another round of Find Waldo Local! All month long, he’ll be sneaking around Old Town businesses. Find him for a chance to win big!

50th Anniversary Celebration
2026-06-28 11:30 - 13:00 | Godfrey Miller Center, 28 South Loudoun Street, Winchester, V, 22601, United States
50th Anniversary Celebration!
Join us as we celebrate 50 years of serving our community with a special anniversary gathering featuring lunch, fellowship, and cherished memories. Mark your calendars for Sunday, June 28 at 11:30am, at Godfrey Miller Center (28 South Loudoun Street). We look forward to honoring the past and celebrating the future together!

KidzFest
2026-06-13 12:00 - 17:00 | Loudoun Street Pedestrian Mall
KidzFest is returning to Old Town Winchester on Saturday, June 13 for an afternoon full of family-friendly fun, activities, entertainment, and community programming throughout the Walking Mall.
Hosted by Friends of Old Town and presented by Rise Orthodontic Studio, KidzFest brings together local businesses, organizations, vendors, performers, and activity stations designed to create an interactive and energetic day downtown for kids and families of all ages.
This year’s event will include:

Kids activities and games
Face painters and caricature artists
Music and entertainment
Dunk tank
Photo booths
Vendors and community organizations
Giveaways throughout the day
Family-friendly experiences across Old Town

Whether you’re spending the afternoon downtown, grabbing lunch, shopping, or just looking for something fun to do with the family, KidzFest is all about creating a lively and welcoming community atmosphere in the heart of Old Town Winchester.
Saturday, June 13
12–5 PM
Old Town Winchester Walking Mall
Presented by Rise Orthodontic Studio.

Author Event: Stephanie S. Gardner - Mattie’s Story: Adventures in Dayton
2026-06-13 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Stephanie Gardner’snovellas are inspired by real people, places and events from the historicalShenandoah Valley and Blue Ridge Mountains. From mountaineer history inpost-Civil War Thornton Gap to Victorian life in the town of Dayton, thesestories are sure to please fans of regional fiction and folklore.

Author Event: Steve Carpenter - The Allure and Peril of the Appalachian Trail
2026-06-07 12:00 - 14:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Contrary to Bill Bryson’s popular book’s title, hiking the Appalachian Trail isn’t just “a walk in the woods.” It is a long and strenuous hike and danger abounds for unwary hikers. For many, the risk of peril adds to the allure of the trail. In this enthralling volume, long-time hiker Steve Carpenter explores the joys of the trail and the misfortunes that have befallen hikers. Including some history of the trail, Carpenter relays encounters with wildlife, accidents on the trail, stories of sex and murder, and meetings with larger-than-life thru hikers. Stop by the bookstore and grab a signed copy from author Steve Carpenter!

Author Event: Haley Hodges - Eros Rex
2026-06-06 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Eros Rex introduces Haley Hodges’ vibrant poetic voice, at once sensual and reverent, restless and devoted. Hodges’ sonically impactful lines are brash and honest in addressing God, and these poems viscerally situate spirituality in the everyday world, whether in Burger King or the back yard. Come meet Haley at the shop and grab a signed copy!

Author Event: Sarah Lauck - The Weeping Willow
2026-06-06 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Sixteen-year-old Rene DuPont has endured a lifetime of pain, abuse, and abandonment—until one night of horror and fire leaves him scarred but not broken. From the ashes rises Red, a teen forced into adulthood, survival, and ultimately healing. With the help of a long-lost grandmother, a mysterious estate in Virginia, and secrets hidden in the trees of Mourner’s Crossing, Red must reckon with his past to unlock his future. The Weeping Willow is a gripping coming-of-age mystery rich in emotional depth, resilience, and the unbreakable bond of found family.

YDC Wildflower Art Night
2026-05-28 18:30 - 20:30 | Youth Development Center, 302 S Loudoun Street, Winchester, V, 22601, United States
This spring, The YDC invites community members to gather for Wildflower Art Night, a creative evening centered around abstract painting, reflection, and community connection.
Taking place on Thursday, May 28 from 6:30PM–8:30PM at The YDC, A Center for Youth & Community in Winchester, this special event will be led by local artist Lindsay Browning and inspired by the colors, movement, and natural beauty of wildflowers in the Shenandoah Valley.
Designed for both beginners and experienced artists, the evening will guide participants through an expressive abstract painting practice that encourages playful experimentation with color, texture, and composition. Through gentle creative prompts, participants will explore themes of growth, renewal, and connection to the natural world while creating meaningful artwork in a warm and welcoming atmosphere.
The evening will include:
? A guided abstract painting session with Lindsay Browning
? All art materials provided, including canvases, paints, brushes, and aprons
? Light refreshments, music, and a relaxed creative setting
? A completed abstract wildflower painting to take home
? A sunflower seedling for each participant to continue nurturing beyond the event
Wildflower Art Night is open to teens and adults ages 12+ and reflects The YDC’s ongoing commitment to fostering creativity, accessibility, and community enrichment through arts-based programming.

Author Event: June Smalls - Hear Them Sing
2026-05-16 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
High in the treetops, way up in the sky, there’s a symphony. The chirring of an American robin, the whistle of a black-capped chickadee—these birdsongs all come together to create the sounds of your backyard. But do you know which sound belongs to which bird?
With this fully illustrated guidebook and soundboard, kids can learn the whistles, chirps, and coos of 14 birds from North America by simply pressing a button. Each page comes with stunning watercolor illustrations from Zev Labinger that capture the birds in their natural habitats, accompanied by fun facts from June Smalls that cover everything from population size to nest structure. And you’ll find true-to-size illustrations of each bird’s egg! Packed with everything a kid needs to stay entertained and engaged, Hear Them Sing is the best first guide for young birders and outdoor adventurers. All you have to do is look up!
Join us in welcoming back author June Smalls for her new release book!

Author Event: Bryan Lienesch - Safe Harbor
2026-05-16 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
Help us welcome back Bryan Lienesch and celebrate his latest book! Jackson Clay returns, and in an attempt to relax in the wilderness, finds himself and his friend embroiled in a seemingly spontaneous murder. Join him as he talks with a host of peculiar characters. Can you solve the mystery?

Author Event: C.N. Steinhour - The Lifesaver
2026-05-09 14:00 - 16:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
When Avery Taylor stumbles across an unconscious classmate in the river, he fears a life is at stake. Although his quick actions are enough to save Tristan, Avery’s left with more questions than answers about that fateful night: What was Tristan doing in the river in the first place? Could all the rumors about him be true? And why should Avery care so much, anyway?Joyful and raw, The Lifesaver is an emotional look at the human connection and how it can change a life in more ways than one.

Mother's Day Bloom Bar
2026-05-09 12:00 - 16:00 | Kimberly’s, 135 N Braddock St, Winchester, VA, 22601, United States
Bloom Bar + Brunch = The Perfect Saturday!
Join us the Saturday before Mother’s Day, May 9th from 12-4, for our Bloom Bar with Allison of Dozer Pharms. Stay for bite to eat at The Market At Kimberly’s with a special Mother’s Day menu: cinnamon rolls, avocado toast, and $5.00 mimosas or hot tea + a chocolate truffle.
Bring the kids, do your shopping, and get your Mother’s Day Gift wrapped!

Author Event: Patti Bonesteel - Ramona and Izzy I’ll Be Here for You
2026-05-09 11:00 - 13:00 | Winchester Book Gallery, 7 North Loudoun Street, Winchester, V, 22601, United States
We are excited to welcome Patti Bonesteel to the bookstore! Patti lives inBaldwinsville, NY with her husband, Bob, and their four daughters. After 25years teaching elementary school and a lifelong love of nature, she poured herexperiences into titles like “The Flamingo with Two LeftFeet,” “Amari and the Big Surprise… It’s Not Monkey Bread,””Search!: Adventures of Peyote and Violet,” “Barkley and LeaveIt to the Beavers,” “We Can… and We Do,” and her newest, “Ramona and Izzy I’ll Be Here for You.” She will be at the shop to sign copies of all of her books. Come meet Patti and picked up a signed copy or two!

Winchester Civil War Weekend '26
2026-05-08 15:00 - 2026-05-09 17:00 | shenandoah valley civil war museum
Step back in time during Winchester Civil War Weekend 2026, happening May 8–9 in Winchester.
This two-day weekend brings history to life with expert talks, guided tours, and hands-on experiences across some of Winchester’s most iconic Civil War sites. From kickoff programs and a live podcast on Friday to battlefield tours, artillery demonstrations, and trivia on Saturday, there’s something for both casual history fans and dedicated enthusiasts.
Events take place throughout Old Town and surrounding historic locations, with programming led by historians and local experts. Registration and admission vary by event.
