Shenandoah Apple Blossom Festival

March 17, 2020:  In light of the current COVID-19 pandemic and the CDC’s recent recommendation regarding large gatherings, the Shenandoah Apple Blossom Festival® Board of Directors has made the painful decision to suspend all planning for the 93rd Festival. 


Winchester’s most well-known event the Apple Blossom Festival, now in its 93rd year, is an annual event organized by the private Shenandoah Apple Blossom Festival organization and held in the City of Winchester and Frederick County. Attracting large crowds, the festival includes a week of events such as the Old Town Bloomin’ Wine Festival, Apple Blossom Carnival, dances, parades, band concerts, luncheons, parties and much more. For a full list of festival events and information visit the official website:

Although the event is not organized by the City of Winchester, logistic support is provided by the City. For road closures, changes to parking and other city related information visit the city’s information page at:

A few of the festival highlights are below.


United Bank Bloomin’ Wine Fest

Friday, April 26 @ 3:00 pm – 10:00 pm & Saturday, April 27 @ 11:00 am – 6:00 pm

Old Town Civil War Courthouse, 20 N Loudoun Street

The United Bank Bloomin’ Wine Fest is one of the festivals most popular events! This two-day event is a unique, outdoor wine festival placed in the historic Old Town Winchester. Come down to enjoy three distinctive wine gardens with over 20 wineries, delicious food, and great music while nestled in the heart of Winchester.

Pumps and Pearls Ladies Party

Monday, April 29 @ 7:30 pm – 10:00 pm
George Washington Hotel, 103 E Piccadilly Street
Since Festival beginnings, there have been events just for the ladies. Often the site for these events was the George Washington Hotel. We invite you to join us again this year for Pumps and Pearls in the fabulous hotel ballroom on April 30th from 7:30 to 10 p.m.

Car Credit Nation Apple Blossom’s Got Talent! Finals
Wednesday, May 1 @ 7:00 pm – 12:00 am
Bright Box Theater, 15 N Loudoun Street
Apple Blossom’s Got Talent! – Always striving to do everything in the biggest possible way, the Festival will present the champion of this talent search with a cash prize of $5,000.00 plus other gifts and perks.

Old Town Midway
Friday, May 3 @ 10:00 am – 11:00 pm 
& Saturday, May 4 @ 10:00 am – 11:00 pm
Bank of Clarke County, 202 North Loudoun Street
The Midway, which opens at 10 a.m., features vendors from over twenty states, is full of carnival games, novelty items, and food, such as cotton candy, caramel apples, funnel cakes, and corn dogs, along with a variety of international foods and live entertainment.

Midway Music Schedule:

Friday May 3rd

  • Dill Pickers – 11:00 am to 1:00 Pm
  • Robert Bittinger with Continental Ridge – 2:00pm to 4:00 pm
  • Cazhimiere – 5:00pm to 7:00 pm
  • Push to Start – 8:00pm to 10:00pm

Saturday May 4th

  • Clay Arthur and the Mystic Pistols – 11:00 am to 1:00 Pm
  • Ronnie Johnson Band – 2:00pm to 4:00 pm
  • SV Jazz –  5:00pm to 7:00 pm
  • SHAG – 8:00pm to 10:00pm

BB&T Men’s Commonwealth Luncheon
Friday, May 3 @ 11:00 am – 2:00 pm
Piccadilly’s Public House, 125 East Piccadilly Street
This popular gathering of gentlemen will be reminiscent of the original and complementary to the current Stag Luncheon. The area’s most influential business and community leaders know this is one party not to miss!

Firefighters’ Parade presented by Walmart
Friday, May 3 @ 5:30 pm – 8:30 pm
Handley High School, 425 Handley Blvd
Coordinated by members of the Winchester & Frederick County Firefighters for the 86th year, the Firefighters’ Parade will step off at 5:30 p.m.

Fireworks Display & Night Fest
Friday, May 3 @ 9:00 pm – 11:00 pm
Handley High School, 425 Handley Blvd
Apple Blossom revelers can finish their Friday, at the Nightfest and fireworks display, an area of the Festival that offers something for everyone. Walk from the Firefighters’ Parade to the Handley High School campus, find your perfect spot on the lawn, and watch the fireworks!

Sunrise Medical Laboratories Queen’s Ball
Friday, May 3 @ 8:00 pm – 12:00 am
George Washington Hotel, 103 E Piccadilly Street
Guests will enjoy cocktails and hors d’oeuvres and dance the night away to the sounds of the band Trademark, back by popular demand. The band covers Motown, disco, R&B, pop, rock, contemporary, along with swing and jazz, offering music for anyone to dance to!

Partlow Insurance Sports Breakfast presented by Grange Insurance
Saturday, May 4 @ 8:00 am – 10:00 am
Winchester Moose Lodge, 215 E. Cork Street
The Partlow Insurance Sports Breakfast is a favorite of both children and adults as they have the opportunity to eat with and listen to their “heroes” in sports.

Grand Feature Parade
Saturday, May 4 @ 1:30 pm – 6:00 pm
Handley High School, 425 Handley Blvd
Coordinated by the members of the Winchester Host Lions Club, the Grand Feature Parade steps off at 1:30 p.m. on Saturday, in Old Town Winchester. The parade route stretches from Old Town Winchester, to the Handley School area. This Parade includes local school bands, hand crafted floats, entertainment, and much more from all over our region!


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