KidzFest Courtesy of Visit Winchester

Looking for Shenandoah Valley family friendly festivals? We’ve got them! From kite flying to apple pie eating, take a look at these festivals for Virginia Kids Trail Fun.

2020 Shenandoah Valley Family Friendly Festivals

Festivals are a great way to spend time on the VA Kids Trail. And while heritage and agriculture play a major role in the Valley’s festivals, you’ll also find a few that break the traditional festival mold. We’ve come up with a mix that offers something for everyone. Most are free or low cost.

Spring Family Friendly Festivals

Go fly a kite! No really, take to the skies April 4 at Sherando Park in Stephens City for the Kite Fest. From 10am to 2pm, enjoy vendors, food, and door prizes. Sponsored by Frederick County Parks and Recreation.

Vintage in the ValleyAnd after you fly your kite, take a short drive over to Strasburg for the Vintage in the Valley Festival . The festival actually starts on Friday, April 3, with a Decades Dance that’s open to families with cool vintage games to play. The vintage fashion show on Saturday, April 4, features models from 8 to 80. The Movie “Grease” will be shown under the stars. And on Sunday, April 5, there will be an Ole’ Timers Baseball Game.

Did you know this year marks the 50th anniversary of Earth Day? Celebrate with Northern Shenandoah Valley’s largest Earth Day Celebration. This family friendly event happens April 18, 8am to 3pm, at the Shenandoah County Historic Courthouse in Woodstock.

If your family enjoys art and music, then be sure to put the April 25 Purcellville Music and Arts Festival on the calendar. This free festival is held at the historic Dillon’s Woods and Bush Tabernacle at the Fireman’s Field Complex. Enjoy multiple stages of live music and an art show.

Rounding out the month is the 93rd Annual Shenandoah Apple Blossom Festival, held April 24 – May 3 in Winchester. While many of the festival’s activities charge admission, check out the FREE Fire Truck Rodeo, the low cost Firefighters Parade ($4-$5 admission), and the FREE Sheetz Fireworks and Trex Concert. 

Front Royal Family Fun DayOn May 9, visit Front Royal for the 5th Annual Family Fun Day hosted by C&C Frozen Treats. The festival kicks off at 10am with a parade, followed by a car show, live music, and plenty of fun for the kids. And Old Town Winchester’s popular KidzFest returns May 16, noon to 5pm, on the downtown pedestrian mall. This free event features over 50 interactive exhibits, wildlife “meet and greet” programs, a bike stunt show, and Mandy the Clown.

Summer Family Festivals

Strawberry Festival West Oaks Farm MarketIf you love those luscious red jewels, then head over to West Oaks Farm Market in Winchester June 6 for the 2nd Annual Strawberry Festival. This all day event offers live music, food, kids activities and all things strawberry! WOFM will also host a Peach Festival August 15 and a Fall Festival October 17.

Celebrate Dad a day early at Strasburg Town Park with the Father’s Day Fish Fry Float on June 20. Shenandoah County Parks & Rec will offer kayak (ages 12+) and tube floats (ages 3+). There will also be live music, face painting, a bounce house, petting zoo, and watermelon eating contest. And, of course, fish!

July takes us into celebrating our nation’s birthday Blue Ridge style. We’ll be updating those 4th of July parades and festivals soon. But in the meantime, take a look at what’s in store. And if you’re traveling through the Shenandoah National Park mid-month, be sure to drop in at Skyland for Blackberry Delight on July 18. This free – and pet friendly – event offers live music, dancing, local crafts, pony rides, and kids activities.

Fall Family Festivals

As the temperatures cool down and the leaves change in the Shenandoah Valley, you’ll find a Kids Trail full of family festivals. In addition to the Fall Festival at West Oaks Farm Market, here are a few that caught our eye for family fun.

Edinburg Ole Time FestivalTake a step back into history with the 40th Edinburg Ole Time Festival, September 18 -20. See this little Valley town come alive with music, crafts, a parade, hay rides, entertainment, and food. The month also brings the annual Harrisonburg International Festival on September 26, 12-6pm, held downtown. At this free event, you’ll find ethnic food and dress, international entertainment, crafts, and cultural displays.

And since the area is known for its orchards, we couldn’t pass up the Shenandoah Valley Apple Harvest, September 19-20, at the Frederick County Fairgrounds. Kids under 10 are free with half-price admission for the rest of the gang after 3pm. There’s fun for all ages and this festival is also pet friendly.

More Family Festival Fun

October brings us lots of Halloween happenings and the West Oaks Farm Market Fall Festival. And with the leaves in all their glory, what a great time to be outdoors! Make a weekend in the Valley with the Festival of Leaves October 10 in downtown Front Royal and Hail to the Trail on October 11 in Purcellville.

Festival of Leaves Front Royal VAThe Festival of Leaves features a parade, live entertainment, and living history while Hail to the Trail celebrates Purcellville’s Green Expo and the Chapman DeMary Trail. Need a family friendly place to stay? Then check out Holiday Inn Blue Ridge Shadows where kids eat free. Or plan a camping trip at Shenandoah River State Park.

Round out your Fall festival calendar with the Grilled Cheese & Tomato Soup Festival in Strasburg November 7. Kids under 10 taste for free! Plans for the 2020 festival are in the works, so check back for more details.

While you’re enjoying these terrific Shenandoah Valley family friendly festivals, why not add some nearby stops on the VA Kids Trail. And check Facebook for festival and family fun updates.