Winstigators,

We’re heading into the second weekend of Apple Blossom Festival and this is where it really hits its stride. Here’s a link to all of the remaining events, but if you’re feeling overwhelmed with options, here’s a short list of what’s really worth your time:

Friday, May 1 – Fire Truck Rodeo (Millbrook High School, 9:00 a.m.)
One of the coolest events of the weekend that you’ll appreciate if you’ve got kids. Dozens of fire departments roll in with everything from antique engines to massive ladder trucks and the main event is firefighters running precision driving courses, backing their rigs through cones against the clock. It’s part competition, part skills showcase, and it’s way more impressive than it sounds. The competition starts at 9:30 AM, rain or shine.

Friday, May 1 – Firefighters’ Parade (Downtown Winchester)
This is the right way to kick off the weekend. The same trucks from the Rodeo (plus plenty more) roll through downtown in a loud, high-energy parade that’s super family-friendly and easy to pop into without planning your whole day around it. If you’ve never gone, it’s one of those “why don’t I do this every year?” things.

Friday, May 1 – Fireworks at John Handley High School
After the Firefighters’ Parade head over and claim a spot on the Handley Green, but you might want to plan early since people start laying down blankets by mid-afternoon. There are food vendors and once the sun goes down, you get a tightly packed 20-minute fireworks show synced to music. It’s not a “watch from your car” situation; being on the lawn makes the difference.

Saturday, May 2 – Apple Blossom 10K
If you’re into running and haven’t signed up, you still can. It’s one of the most accessible races you can find and it’s here in your backyard; flat, scenic through downtown and the crowd support is legit with people out on porches cheering you on. Good vibes, good swag, and you’ll feel like you earned your weekend beers. I ran it a couple years ago and had a great time.

Saturday, May 2 – Grand Feature Parade
This is Apple Blossom’s main event and the one everything builds toward. It’s a full on show; massive themed floats, marching bands, dance teams, color guards, Shriners weaving through in tiny cars, local organizations, and enough pageantry to keep your attention the entire time. Come prepared because this one lasts for hours.

This year you’ll see Grand Marshal Jesse Palmer alongside football legend Tim Brown (both also appearing in Friday night’s Firefighters’ Parade) plus all the festival staples that make Apple Blossom a great event. If you’ve got kids, they’ll love it. If you don’t, grab a drink, claim a seat early (seriously) and lay back and relax. If you’re only doing one parade all week, this is the one you want to attend.

It’s also worth mentioning that the carnival’s running all week if you’re just looking to wander and grab some greasy fried carnival food.

Want an escape? Go to the Virginia Gold Cup!
Held about an hour away in The Plains, it’s a completely different vibe from Apple Blossom. It’s horse racing combined with all-day tailgating; everything from thrown-together coolers to full-on catered spreads with table settings that look like weddings. By mid-afternoon it hits that perfect mix of classy and slightly unhinged. Dress up, bring a cooler, and have a great time if you want to check out something different!

Tally Ho Theater, Leesburg - Zoso - The Ultimate Led Zeppelin Experience, May 1, 7pm

Hollywood Casino at Charles Town Races, Charles Town - Hairball, May 1, 8pm - 10pm

The Winchester Book Gallery, Winchester - Asian American and Pacific Islander Heritage Month, May 1

Salamander Middleburg, Middleburg - Soar Under the Stars: Full Moon Night Zip Tour – Flower Moon, May 1, 8pm - 10pm

Apollo Civic Theatre, Martinsburg - Thrift & Bake Sale! 9 AM (Friday and Saturday)

FN Flatbreads Food Truck, Martinsburg - FN Friday at Black Draft Distillery

Tally Ho Theater, Leesburg - Gold Dust Woman: A Tribute to Stevie Nicks and Fleetwood Mac, May 2, 7pm

Summit Point Motorsports Park, Summit Point - Final Bout: Special Stage East, May 2, 10am - 5pm

Village at Leesburg, Leesburg - Leesburg, VA - Paws in the Village, May 2, 1pm - 5pm

Backseat Events, Winchester - The Amish Outlaws, 7PM

Lost Barrel Brewing, Middleburg - Kentucky Derby Party, May 2, 11am - 9:30pm

Run The Greenway, Aldie - Run The Greenway Wellness Expo, May 2, 10am - 4pm

The Winchester Book Gallery, Winchester - Author Event: James and Nichole - Night Before Apple Blossom, May 2, 11am - 1pm

Danceking, Leesburg - Danceking Coffee and Cars, May 2, 6am - 9am

The Catamount Lounge, Front Royal - Honky Tonk Night feat. The Sneaky Snakes, May 2, 8pm - 11pm

Orlean Market, Orlean - Watch Kentucky Derby Live at Orlean Pub - GoldCup After Party, May 2, 3pm - 10pm

Bright Box Theater, Winchester - Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers, May 3, 7pm

Best Buy, Winchester - Booming Car Show, May 3, 9am - 3pm

Orlean Market, Orlean - Cinco de Mayo All-You-Can-Eat Buffet, May 3, 11am - 2pm

Broken Window Brewing Co., Winchester - WildKind Open Table · May, May 3, 3pm

The Studio, Front Royal - Paint Your Pet's Portrait, May 3, 1pm - 4pm

James Wood High School, Winchester - 2026 JWHS FFA Plant Sale, 10 AM

Unique Creations Studio, Berryville - May Maker's Market, May 3, 10am - 3pm

Loudoun Station, Ashburn - RUN THE GREENWAY 2026, 8 AM

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Have fun out there!