Celebrating the Holidays in Winchester, Virginia
The holidays in Downtown Winchester bring together everything locals love about this city: sparkling lights, cozy shops, and festive gatherings that make you feel right at home. Whether you’re hunting for handmade gifts, looking for family fun, or just want to take in the sights, Winchester has something special waiting around every corner.
Winchester’s holiday experiences:
Festive Markets & Local Shopping
Winchester Old Town Winter Village
Downtown’s most charming holiday tradition, the Winchester Old Town Winter Village, transforms the walking mall into a European-style market. Stroll through artisan stalls, sip hot cider, and take in the glow of twinkling lights while supporting local makers and businesses.
Winter Wonderland Christmas Market
The Winter Wonderland Christmas Market is your one-stop spot for unique, handcrafted gifts. With local artisans, baked goods, and holiday décor, this market captures the cozy spirit of the season while making holiday shopping fun and stress-free.
Christmas Makers Market at Homestead Farms
At the Christmas Makers Market at Homestead Farms, creativity takes center stage. From hand-poured candles to homemade jams, this community favorite is a showcase of local talent, and a perfect weekend outing for finding thoughtful, one-of-a-kind presents.
Light Displays & Outdoor Fun
Winchester Holiday Lights Trolley Tour
Hop aboard the Winchester Holiday Lights Trolley Tour and take in the city’s best light displays in style. It’s a fun and relaxing way to see Winchester shine, whether you’re with family, friends, or on a cozy date night downtown.
Walking in a Winter Wonderland at Clearbrook Park
Bundle up and take a stroll through Walking in a Winter Wonderland at Clearbrook Park. With more than a million lights and plenty of photo-worthy moments, it’s a holiday tradition for locals and visitors alike.
Follow the Star Live Nativity Walking Tour
For a more reflective experience, visit the Follow the Star Live Nativity Walking Tour. This moving reenactment of the Christmas story features live actors and animals, bringing the spirit of the season to life in an unforgettable way.
Holiday Tours & Timeless Traditions
Candlelight Tours & Open House
Experience Winchester’s history in a whole new glow during the Candlelight Tours & Open House at Abram’s Delight. This historic home comes to life with traditional decorations, candlelit rooms, and stories of holidays past.
Holiday Tours at Belle Grove Plantation
The holiday season at Belle Grove Plantation stretches across several weeks, and each event brings something a little different to the celebration.
It all begins in late November with the Kris Kringle Outdoor Market, when the plantation grounds come alive with artisan booths, local foods, and festive music. Shoppers can browse handcrafted gifts and enjoy the crisp fall air while taking in the scenic beauty of the Shenandoah Valley.
Then, as December arrives, Belle Grove opens its doors for Holiday Tours inside the historic mansion. Each room is thoughtfully decorated to reflect both period elegance and holiday warmth, with docents sharing stories of how families once celebrated the season. Together, these two events make Belle Grove a must-visit destination, offering a perfect mix of local craftsmanship, history, and holiday cheer.
For tour and market dates, visit Belle Grove Plantation’s official event page.
Celebrate the Season at The Local
When you live at The Local, Winchester’s best holiday events are practically right outside your door. From evening strolls through Old Town to cozy nights spent decorating your apartment, it’s easy to make the season bright when you’re in the heart of it all.
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Enjoy the magic of the holidays where local spirit shines brightest, right here at The Local in Downtown Winchester, VA.