Parrot Head – Jimmy Buffett Beach Party
Thursday
Afternoon – Check In & Chill Out
Roll into Winchester and check into one of the many cozy, convenient hotels around town! Drop your bags and head to Piccadilly Brew Pub for a fruity Parrot Head cocktail and tasty bar bites to kick off the weekend.
Evening – Buffet Vibes & Barefoot Dancing
Time to party like it’s always 5 o’clock! Head over to Tolley Dental Zone at Shenandoah University’s Athletics & Events Center for the Jimmy Buffet Beach Party, featuring A1A, the Official and Original Jimmy Buffett tribute band. Throw on your Hawaiian shirt, grab a drink, and dance the night away with your fellow Parrot Heads!
Friday: Cheers, Music & Good Times
Ladies – It’s a Bloom Thing
Start your Friday with the Bloomers’ Luncheon, a lively, ladies-only event featuring live music, festive energy, and an open bar stocked with beer and wine. It's the perfect excuse to gather your girlfriends, enjoy a great meal, and show off your best pink and green attire.
Gents – Stag Shenanigans Await
The guys can head over to the Stag Luncheon, a festival favorite built for fun. Think bourbon, cigars, cornhole, and great conversation — no speeches, just an afternoon of relaxed, no-frills enjoyment.
Midday into Evening – Food, Fun, and Festival Magic
After your luncheon, return to your hotel to regroup and refresh before heading to Old Town Winchester’s Midway. Indulge in classic carnival favorites like corndogs, funnel cakes, and steak and cheese subs. Enjoy the festive energy as you explore games and activities that bring out the kid in everyone.
Grab a spot along the Firefighters Parade route for one of the festival’s most beloved traditions, featuring all things honoring first responders, marching bands, and more. While you're there, take in the spirit of the community as homes along the route proudly show off their pink and green decorations. After the parade, head to the Handley High School campus for a spectacular fireworks show at dusk. The display is choreographed to music and offers a stunning conclusion to a day full of celebration.
Saturday: Midway Delights & Parade Highlights
Morning to Early Afternoon
Start your Saturday with a relaxed stroll through Old Town Winchester, where the energy is building and the festival is in full swing. Grab a locally roasted coffee or a Bloody Mary from one of the downtown cafés and explore the charming shops, art galleries, and pop-up vendors lining the streets.
Catch up with friends, people-watch, or find a cozy patio to relax before heading to the big show.
1:30 PM – Grand Feature Parade
Grab your seat along the parade route early — they go fast! At 1:30 p.m., the Grand Feature Parade steps off, bringing marching bands, celebrity appearances, dazzling floats, and community pride through the heart of Winchester. It’s the highlight of the weekend and a true Apple Blossom tradition.
