The Disneyland ‘first pickle’ award that’s almost impossible to win

Originally published by SFGATE on July 23, 2023

Written by Julie Tremaine


The Disneyland ‘first pickle’ award that’s almost impossible to win

I was sitting in my salon, mid-haircut, when I first heard the legend of the first pickle.

“The first what now?” I asked my stylist.

“The first pickle,” she said. “It’s a real thing. You get an award if you buy the first pickle of the day from one specific pickle cart at Disneyland.”

The legend is real. The first person of the day to purchase a $3.99 pickle from the fruit cart midway down Main Street in Disneyland Park gets a special “first pickle” pin. Simple, right? As I would soon find out, it was the complete opposite of simple. Trying to get the first pickle turned out to be one of the most difficult things I’ve ever done at Disneyland.

First, there was the planning stage. Disneyland starts letting people into the park half an hour before rope drop: If the park opens at 8 a.m., for example, the gates open at 7:30 a.m. But you can’t just saunter up at 7:30 a.m. expecting to get straight through. There’s parking to consider. Security lines. Trams to Downtown Disney. Plus, you’ll need to get past all the people queued up to rope drop who will inevitably have gotten there earlier.

(For those of you who don’t obsess over Disneyland timetables, “rope drop” is the term for opening the park for the day. Guests can be on Main Street as soon as the turnstiles open, but physical ropes prevent them from going into the lands until the ropes drop at the actual time of the park’s opening.)

Monday, July 17, was going to be the day. I got up at 5:20 a.m. and left my house at 6:15 a.m. At that hour, traffic is usually pretty light to Disneyland, so I thought it would take me about 35 minutes. I was wrong. Bumper-to-bumper traffic made the drive an hour. Rather than park in the Disneyland garage and be slowed down by the long security and tram lines, I parked across the street from Disneyland’s Harbor Gate, at the Anaheim Hotel. It costs $30, less than Disney’s standard $35, and it’s the shortest walk into Downtown Disney through reliably quicker security.

I was parked by 7 a.m. and walking into the plaza in front of the gates at 7:15 a.m. That’s when I saw it: thousands of people lined up to get into the park.

I had forgotten. It was Disneyland’s birthday. The internet may think theme park attendance is down this summer, but that’s because seemingly every person who planned to go to Disneyland this season waited until that day.

Still, the timing wasn’t as bad as when I went in search of the park’s elusive $20 candy cane, going on a day it was raining so heavily that the rain was coming down and then spraying back up. This time, I was through the gates at 7:24 a.m. and among the first few hundred to make it onto Main Street. It was a beautiful moment. Hundreds of cast members were all lined up on the sidewalks, waving and greeting everyone as we walked toward Sleeping Beauty Castle.

By 7:25 a.m., I was at the cart. “Did I do it?” I practically shouted to the cast members working the cart. “Did I get the first pickle?”

“No,” one said. I had missed it by a minute or two. Who wants to eat a pickle for breakfast anyway? I thought unhappily as I walked off to find a way to kill the next 30 minutes before the park opened. But I couldn’t stop thinking about it. My technique was solid. My shortcuts were on point. It was just an issue of timing. I knew if I did it again, that briny prize would be mine.

Fast-forward three days. I shifted everything back by 20 minutes. Up at 5 a.m., in the car at 6 a.m., at the gates by 7:05 a.m. This time, I was second in my line, which put me closest to the cart and the mythic first pickle. Pass scanned at 7:18 a.m. Through the turnstile at 7:20 a.m.  There were so few people in the front line of guests down Main Street that I could count them: About 40 people were walking in step or slightly ahead of me.

I got to the cart.

“Were you trying to get the first pickle?” the cast member asked me.

“I am!” I said.

“Well, you did it!”

I was overcome with a specific sense of victory that comes from winning something very difficult yet ultimately inconsequential. Like a Sunday crossword, only with a lot more getting up before dawn. I took a picture and then reached for my salty spoils. As I grabbed a pickle, a tiny hand jutted out to the barrel.

“Did I get it?” she asked. She couldn’t have been more than 10. And she was wearing a “happy birthday” pin. She looked at me and then at the cast member, who said I had won it that day. Her shoulders fell. She looked searchingly at her mom, who was powerless to fix the situation.

“Hold on a second,” I said to the girl. “I’ll take a picture of the pin, and then I’ll give it to you.”

“No,” the cast member said. “You both won. It was a tie today.” (I have said it before, and I will continue to shout it from the rooftops: There would be no Disney magic at all without cast members, and they deserve a lot more than they’re getting paid.)

She handed us our celebratory first pickle awards, with the reason for celebrating written on the front and the date on the back. The girl’s was modified with a birthday message. I was glad I could keep my pin. It was so dumb, but winning it took a lot of effort.

I didn’t want a pickle for breakfast, though. I wanted a Haunted Mansion April-December Churro, which was covered in fresh strawberries and therefore technically a smoothie. I didn’t snack on that pickle until 11 a.m. when I was park hopping to Disney California Adventure.

I had heard the first pickle award was only at that one Main Street cart, but curiosity stopped me at Mortimer’s Market, the California Adventure equivalent and first place geographically in the park to get fruit and pickles.

“Do you do the first pickle award here?” I asked the cast member.

“We do,” she said. “But it’s already been claimed for the day.”