Winchester Wings & Wheels

Can you think of a better way to spend a Saturday in the Valley than with family and friends checking out the coolest cars and aircraft?
Fun for all ages, this event will feature classic cars, muscle cars and exotics, and a variety of aircraft will be on display. There will be plenty of food, exhibitors, vendors, and entertainment!

There will also be a judged car show component of the event and prizes and dash plaques will be awarded.

The event will be free and open to the public, however donations will be accepted throughout the day. Proceeds will benefit Arc of the Northern Shenandoah Valley, an organization for people with developmental disabilities, their families and support persons. In addition to a variety of support services, Arc also provides a familiarization program for families with affected family members to help them navigate public air travel and airports, enabling these families to become comfortable with and enjoy air travel.

The event will run from 10am-2pm on Saturday, June 1 with Sunday, June 2 as the rain date.

Free parking, restrooms, food vendors, a kid zone, and more will be available on-site.

Strawberry Festival

Come out for West Oaks Farm Market’s First Strawberry Festival! Fun for the whole family.

If you are a strawberry lover, you DO NOT want to miss out!

Saturday, June 1st

Pick-your-own Strawberries
LIVE MUSIC OUTSIDE (Weather permitting)
feat. Chris Gray and Whitney Dick, and Blue Ridge Rain
Tractor Bounce House
Food Vendors
Hand-Dipped and Hand-Rolled Ice Cream
Kettle Korn
Hylton Clark Bear Mtn Garden BBQ Chicken Dinners
Kids Activities
Strawberry samples everywhere!
Strawberry wine, hard cider, and more!
Delicious strawberry treats!

It will be a strawberry filled day, mark your calendar now!

Garden Fest

Northern Shenandoah Valley Master Gardener Assocation’s annual Garden Fest at Belle Grove will be Saturday, June 1, 8 a.m. – 3 p.m. with free admission and free parking.

It will include:

Hands-On Workshops,
Garden and Specialty Vendors,
Children’s Activities,
Second Hand Rose Rummage Sale,
Birdhouse Contest
Garden Tool Sharpening,
Touring of the Historic Belle Grove Manor House 10 a.m. – 4 p.m. ($5 for those 12 and older, 11 and younger free of charge)
Raffles, Food, And More . . .

More Information

Newtown Heritage Festival

This free family festival includes a parade, food vendors, kids activities, live entertainment, fireworks, and more. Walk into history and learn about the early days of Stephens City as you visit the Stone House Foundation Museums – the Transportation Exhibit at the Stephens City Schoolhouse, Newtown Tavern, Argenbright House & Shed, Stone House, and Steele & Brother Store (all on Main Street).

The event takes place up and down Main Street from Newtown Commons to the Old School grounds. (5165 through 5516 Main Street)

On Friday, enjoy music performances by Crosswinds and Souled Out.

Parade starts at 2:00pm on Saturday, May 25th and features the Sherando High School Marching Band, emergency vehicles, veteran groups and many many more! Don’t forget to stick around for one of the best fireworks displays in the Valley at dusk. We hope to see you there!

Friday: 6:30-10pm
Saturday: 10am-Fireworks at Dusk


Old Town Winchester’s popular KidzFest, presented by Valley Pediatric Dentistry, returns Saturday, May 18th. This free, family-friendly event features over 50 interactive exhibits highlighting education, art, music, sports and more. It will be held on the Loudoun Street Mall from 11:00 a.m. to 5:00 p.m.

KidzFest activities and exhibits will take place primarily on the Loudoun Street Mall and the Old Town Courthouse lawn throughout the day, petting zoo, games, live performances and more. Also, do not miss Fort Loudoun History Day!

New this year, there will be bike stunt shows where a stuntman will jump across obstacles and teach helmet safety. Wildlife Ambassadors will be performing several shows with meet and greet sessions with the animals. Mandy the Clown will also be back for two shows, interacting with the kids and having a good time on the Mall.

This is a great family-friendly event to showcase Old Town Winchester’s exciting atmosphere and for parents to discover upcoming summer activities.

Civil War Historical Impressions

The Civil War Historical Impressions, Inc. will be joining us for the weekend. CWHI is an independent 501(c)(3) non-profit organization. They are a group of Civil War Educators, Living Historians and Reenactors committed to teaching through lectures, encampments, school events and battle scenarios to name a few. Come meet “Stonewall” Jackson and Dr. McGuire, among others. Kid friendly and free. For more information on the CWHI, please call Harry Sonntag at (267) 760-5716.

Scottish “Backyard” Highland Games

The KBA and Clan Adrenalin will host a “backyard” Highland Games. The backyard game is a smaller one than the one we will host in July, with primarily the competition taking place. The competition will benefit Warrior 360, a veteran sponsored 501(c)(3) that supports veterans with everything from medical care to housing needs. A contingent of wounded warriors will be competing at these games.

Bagpipers will play throughout the day.  Shaffer’s BBQ will be on hand to sell refreshments and otherwise support the games. Please bring your own chairs. The games will start at 9 am.

The Steadfast Toy Soldier

The Virginia Youth Ballet Presents:

“The Steadfast Toy Solider”

The Steadfast Toy Solider tells the story of Sarah who receives a doll house and dolls on her birthday. The evening after her party, Sara discovers the dolls have come to life. Her favorite dolls, a soldier and a ballerina are provoked by the mischievous Jack-in-the-Box. The soldier tries to protect the other dolls, but the Jack-in-the-Box throws the soldier over a wall. The soldier ends up in the sewer where he encounters sirens and creatures. His journey in the sewer ends when he is swallowed by a giant fish, but by a miraculous twist of fate, he returns home to Sarah.


All seating is general seating.
Tickets are $8 and can be purchased either at the door or in advance.

Shows at 11am and 2pm.