Winchester is the oldest city in the Commonwealth of Virginia and residents share a strong sense of tradition, reflected in the numerous annual events that can be enjoyed in our area. From concerts and festivals to seasonal activities like ice skating and apple picking, Winchester’s annual events offer something for every member of the community! Below is a list of some of our favorite yearly celebrations:
Celebrate all things Irish, Scottish, Welsh, and Breton at Celtic Fest! Enjoy St. Patrick’s Day in Old Town Winchester and sample delicious food and drinks with live music, dancing, and more. Cultural displays and artisan vendors help you to explore Celtic culture and allow you to shop for unique items. Several local businesses share in the festivities with activities of their own – join us in Old Town for a Celtic spree!
Shenandoah Apple Blossom Festival
The Apple Blossom Festival is a favorite in the Winchester community, bringing together thousands of people each year to celebrate the arrival of spring and blossoms throughout the region. Residents and businesses decorate for the event and sport the official colors of the festival – pink and green! Since the first festival in 1924, the event has developed into a ten-day celebration featuring more than 30 events, two giant parades, dances, concerts, a carnival, a 10K race, a golf tournament, a wine festival, and more!
Bloomin Wine Fest
Kick off the Shenandoah Apple Blossom Festival at the “Uncork the Bloom” event! Enjoy live entertainment, great food, and a robust offering of Virginia wines and ciders. Admission includes a souvenir wine glass and access to tastings from many of Virginia’s finest wineries and cideries. Even if wine isn’t your thing, prizes, giveaways, and tasty cuisine from our local restaurant providers are worth the trip!
Hop Blossom Craft Beer Festival
The Hop is the original Old Town beer festival! Beer lovers can gather to taste beers, learn how to brew, and share experiences at this craft brew-friendly event. Local vendors join more than 40 craft breweries to create an event devoted to the appreciation of beer.
Your children will thank you for planning to attend KidzFest in Old Town Winchester! This fun, free day of activities is a great way to entertain the whole family and connect with your community. Enjoy hands-on entertainment, arts and crafts, educational opportunities, music, games, workshops, and more.
Frederick County Fair
The annual Frederick County Fair is a delightful blend of classic farm events including livestock judging, rodeo, pageants, and crafts complemented by exciting entertainment featuring monster trucks, live music, and a talent show! This is an excellent opportunity for your family to connect with the agricultural industry that surrounds our city, and a fun way for kids to learn about farming.
Skyline Indie Film Fest
The Skyline Indie Film Fest brings the best in new, independent, undistributed films and original screenplays to Winchester. This thoughtfully designed festival aims to nurture cinematographers and expand the vision of artists and encourage them to produce their own work in the indie spirit. It is also a delightful festival for film lovers of every genre, and a chance to see movies, unlike anything you’ve seen.
Shenandoah Valley Apple Harvest Festival
This family and pet friend event gives you the most bang for your buck! Admission includes free inflatables, live music, the Apple Pie Eating Contest, Apple Pie Judging Contest, Canine Challenge Course, and a Classic Car and Hot Rod Show. Local vendors and artisans offer unique handmade creations, and you can enjoy the “Tap & Cork” Cider and Beer tasting and live music. You can expect plenty of tasty apple treats in addition to BBQ, crab cakes, turkey legs, burgers, hot dogs, pizza, ice cream, kettle corn, lemonade and so much more. You won’t want to miss this event!
Celebracion of Winchester
Expand your horizons with this family-friendly event celebrating Hispanic Heritage Month. Sample authentic Latino food, take dance lessons, listen to Latin music, and enjoy a musical petting zoo, face painting, arts and crafts, and activities for kids. This is a unique opportunity to experience another culture and have some fun doing it!
Old Town Winchester Oktoberfest
Old Town Winchester Octoberfest features Virginia breweries and attracts a sold-out crowd. Shop and dine in the Winchester Old Town Pedestrian mall and sample wine, cider, and beer from local breweries including Winchester Brew Works, Vibrissa, Alesatian, Escutcheon, Old Town Cidery, and more! Crim’s legendary kettle corn, the Shenandoah University Band, and a photo booth sweeten the venue for extra fun.
Holiday Parade & Tree Lighting
Join the Winchester community for that special type of holiday cheer that accompanies the Old Town Holiday Parade! Floats, bands, and local organizations create a beautiful moving display and fill the air with the spirit of the season. Santa will make an appearance, too, to help make the season bright! Finish off the parade with the annual tree lighting ceremony for a perfect beginning to the holidays.
Walking in a Winter Wonderland
This display set to music will fill you with delight and the wonder of winter as you walk along the path at Clearbrook Park. Warm up with hot chocolate and cookies, or meet with Santa and Mrs. Claus where kids can tell Santa what they want during the holidays. This magical stroll through a winter wonderland is a tradition you’ll want to repeat every year!
Winchester offers a wide array of traditions and community events – these are just a small sample of all the wonderful annual events you can enjoy in our city! To stay up to date with even more events in our community, check in regularly with our Events in Winchester! We regularly post happenings we think our residents would love. Find the perfect event for you and your family.