14 Annual Events in the Shenandoah Valley That You Won’t Want to Miss

No matter what time of year you visit the Shenandoah Valley, there is always something new and fun to experience. This is especially true since our local calendar is filled with a wide variety of exciting events throughout the year. From food festivals to cultural celebrations, you won’t want to skip a single one! Just to get you started, here are some of our favorite annual events in the Shenandoah Valley that we’re sure you’ll want to add to your itineraries.

If you’re planning a visit to the Shenandoah Valley soon, you won’t want to be without our free online Vacation Guide! This handy vacation planning tool will help you find all the best recommendations for things to see and do in our area, including even more annual events in the Shenandoah Valley. Request your free copy today and we’ll see you soon!

14 of the Best Annual Events in the Shenandoah Valley

1. Civil War Weekend (March)

The Shenandoah Valley is rich with history and historic sites, particularly those related to the Civil War-era. During one weekend in March, you’ll be able to take a step back in time and discover more about the area’s involvement in the war by experiencing living history demonstrations. Opportunities include talks from renowned historians, field trips to notable historic sites, and more fun events that will grant you with a deeper understanding of the Civil War and the Shenandoah Valley’s extensive history.

2. St. Paddy’s Celtic Fest (March)

Did you know that many residents of Winchester, VA have Scottish and Celtic roots? To celebrate their heritage, the people of the Shenandoah Valley host a huge St. Patty’s Day event. Every year, the town puts on the St. Paddy’s Celtic Fest for both locals and visitors alike to enjoy. Performers are stationed along the streets and in local businesses. The best part? There is no admission charge to watch any of them! Plus, a portion of the food and beverage goes to the cause the event sponsors, Habitat for Humanity.

3. Of Ale and History Beer Festival (May)

This Middletown, VA Beer Festival has quickly grown to become one of the most popular Shenandoah Valley events. Every spring, Belle Grove Historic Plantation puts on this event so guests can choose from over 60 beers and ciders to taste. Some are imported while others are local. Festival-goers can enjoy their brews as they listen to the live bands playing throughout the day. Cheers to that!

4. Wine and Craft Festival (May)

Since Northern Virginia is abundant with incredible wineries, it only makes sense that there should be an event dedicated to spectacular vintages. The Wine and Craft Festival is held in historic Downtown Front Royal and features more than seven blocks of vendors and about 20 local wineries offering their most popular selections. Browse through the stands to find unique artwork and merchandise you won’t be able to find anywhere else! Popular goods found here are handmade jewelry, wine glasses, pottery, paintings, antiques, and more.

5. Shenandoah Apple Blossom Festival (May)

Celebrate the start of spring by attending the Shenandoah Apple Blossom Festival! For more than 100 years, this festival has welcomed the warm weather to the area with 10 days of apple blossom-themed fun such as parades, a carnival, parties, dances, and more! Hundreds of people attend this event each year, so be sure to book your stay with us well in advance!

6. Virginia Herb Festival (June)

Whether you are a foodie, a beer connoisseur, or a gardening enthusiast, you will have a blast at the Virginia Herb Festival! The main events of this yearly fest are beer tastings, local chef demonstrations, live music, and vendors selling handmade crafts. The goal of this festival is to bring a fun event to the area centered around herbs and agriculture.

7. Shenandoah Valley Blackberry Festival (July)

Summer is blackberry season in the Shenandoah Valley! To commemorate the harvest of this local fruit and the natural beauty of the valley, our area puts on the annual Shenandoah Valley Blackberry Festival. This is one of the most beloved Luray, VA events and a must for foodies! You’ll sample some true culinary masterpieces using the sweet-tart blackberry from Skyland chefs. They will create special blackberry-infused dishes for your indulgence, including a crumbly blackberry cobbler, mouthwatering blackberry barbecue, and more! While you eat, enjoy live music, dancing, local crafts, pony rides, and other fun activities surrounded by the beautiful landscape.

8. Winchester Greek Festival (August)

Opa! The Winchester Greek Festival is the perfect opportunity to immerse in the vibrant Greek culture, taste delicious food, and meet interesting new people. The main draw for this event is the wide variety of succulent Greek dishes prepared by the Winchester Orthodox Church. The incredibly rich and diverse array of foods are the culmination of thousands of years of good cooking, eating, and living. From the moment you take a bite, your taste buds will be sent on a culinary journey to the Greek Islands. Also, don’t forget to bring your dancing shoes so you can learn traditional Greek dances!

9. Route 11 Crawl (August)

Antique lovers and thrift shopper, unite! The annual Route 11 Crawl consists of yard sales, sidewalk sales, and vendor booths full of trinkets and one-of-a-kind items along Route 11, also known as Old Valley Pike. Take in the gorgeous views the Shenandoah Valley has to offer as you travel from town to town during this event. You’ll be sure to find unique items and gifts that you can’t get anywhere else!

10. Apple Harvest Festival (September)

There are several reasons why the fall season is one of the best times to be in the Shenandoah Valley, and the Apple Harvest Festival is one of them. Hosted by the Rotary Club of Winchester, the Shenandoah Valley Apple Harvest Festival is one of our area’s most popular fall events with an approximate attendance level of 7,500. There will also be nearly 150 artisans and crafters in attendance that will offer their best products and creations directly to you. Apple-themed treats are made available to festival attendees, so be sure to stop by to try delectable creations like fresh apple cider, apple pie, and apple butter.

11. Vintage Woodstock Festival (September)

This is an event for people of all ages! The Vintage Woodstock Festival brings everyone together for a full afternoon of food, live music, dancing, a wine and beer garden, and much more. A popular new feature of this event is a sidewalk art contest, in which young artists from all over the region compete for the People’s Choice Award. Be sure to stop by so you can join in all of the fun and cast your vote!

12. Shenandoah Valley Music Festival (September)

The Shenandoah Valley Music Festival has been reaching their goal of bringing live music to the area for more than 55 years! To celebrate the end of summer, the not-for-profit organization hosts eight concerts. Past performers have included Arlo Guthrie, Bruce Hornsby, LeAnn Rimes, and more. They switch up the music genres each concert, so you’ll be sure to find one that you can enjoy!

13. Walking in a Winter Wonderland (November and December)

Held each year in Clearbrook Park, Walking in a Winter Wonderland puts all who visit in the Christmas spirit! The annual light show lets you see fantastic holiday-themed displays as you take a magical stroll through the park. When it gets a bit chilly, retreat to the cabin for hot chocolate, Christmas cookies, and meetings with Santa and Mrs. Claus.

14. First Night Winchester (December)

Celebrate New Year’s in Shenandoah Valley with First Night Winchester! A favorite of local events in Virginia, this festival of the arts includes live performances, visual creations, and a street full of excitement. Enjoy the famous “Apple Drop” before a spectacular fireworks display!

Need a Place to Stay For These Events? Look No Further Than The Inn at Vaucluse Spring

romantic cabin getaways in VirginiaDid you find your favorite annual events in the Shenandoah Valley on this list? Treat yourself to one of the most unique and beautiful accommodations in our region! Our gorgeous resort is less than a half hour away from Winchester, making it the perfect place to stay during any event. You’ll love our calming spring and breathtaking gardens you can stroll through between festival events. Choose from both cozy rooms in the Manor House and private cabins to create your perfect stay. We have everything you need for a Virginia getaway, and you’ll even get a delicious homemade breakfast each morning of your stay. What are you waiting for? Book your stay today!