A large group of people dressed in Halloween-themed outfits pose in front of the giant Mickey pumpkin on Main Street at Disneyland. The group wears a mix of orange, black, and festive clothing with pumpkin patterns, Halloween dresses, themed mouse ears, and accessories. Some hold decorated parasols and pumpkin buckets, while a few ride mobility scooters decorated with pumpkins. The background shows Main Street buildings with fall garlands and banners.

A large group of people in Halloween-themed outfits pose together in front of Sleeping Beauty Castle at Disneyland. Many are wearing orange, black, and pumpkin-themed clothing and accessories, including skirts, dresses, shirts, and mouse ears. Several hold parasols, pumpkin buckets, or decorations, and a few are using mobility scooters decorated for Halloween. The group is smiling and gathered closely, with the castle’s blue and gold spires visible in the background.

A group of people dressed in festive Halloween outfits pose together in front of the giant Mickey pumpkin on Main Street at Disneyland. The group wears a mix of orange, black, and seasonal clothing with pumpkin patterns, mouse ears, parasols, and themed accessories. Some hold pumpkin buckets or umbrellas with jack-o’-lantern faces, while a few ride decorated mobility scooters. The background shows Main Street buildings and lamp posts draped in orange and yellow fall garlands.

#MainStreetPumpkinDay 2025 was officially A BLAST!!!

If you’re looking for an inclusive, fun group of folks to hang with at #Disneyland, look no further! It’s a great way to make friends and we meet up at all the other big theme days throughout the year.

#Diversity #Halloween #Disney

Event schedule graphic for “Obscure Weekender Leisure Society – Main Street Pumpkin Day.” Decorative border of pumpkins, flowers, and vines with a small ghost peeking over a banner. The schedule reads: 11:00 – Kick Off & Goodie Bags (Main Street Opera House) – orange box 12:00 – Pumpkin Pics (Giant Mickey Pumpkin photo spot) – green box 1:30 – Mark Twain Riverboat (ride together & take pics) – teal box 5:30 – Scavenger Hunt Buttons (in line for Castle Photo Pass) – purple box Group Castle Pic (Castle Photo Pass spot) – black box Bottom corner features a white pumpkin with Mickey ears, bow, and flowers that reads “Main Street Pumpkin Day.”

Map graphic of Disneyland’s Main Street area highlighting the Kick Off & Goodie Bags meetup at 11:00 AM. The map labels buildings including Main Street Cinema, 20th Century Music Company, Main Street Magic Shop, Disney Showcase, The Mad Hatter, and The Disneyland Story presenting Great Moments with Mr. Lincoln. A large orange Mickey icon marks the location at the Opera House. Decorative border with pumpkins, flowers, vines, and a small ghost. Bottom corner shows the Main Street Pumpkin Day logo with Mickey ears and a white pumpkin.

Orange and white event graphic titled Kick Off & Goodie Bags. Decorative flourish separates the header from the details, which read: “Find your Ghostesses in the ❄️ air conditioned ❄️ gallery area of the Main Street Opera House. We’ll hand out goodie bags to the first 25 Pumpkin Day folks to arrive and scavenger hunt rules then watch Walt Disney – A Magical Life.”

Countdown to #MainStreetPumpkinDay 9/28/25 🖤🎃🖤🎃 This schedule will stay pinned and you can find more information at owlsociety.life/pumpkin-day-2025

#Disneyland #UnofficialDisneyDay #DressUp #Halloween #HalloweenTime #DisneyHalloween #DisneyAnaheimResort #California #MeetUp #SoCal #Disney

Event schedule graphic for “Obscure Weekender Leisure Society – Main Street Pumpkin Day.” Decorative border of pumpkins, flowers, and vines with a small ghost peeking over a banner. The schedule reads: 11:00 – Kick Off & Goodie Bags (Main Street Opera House) – orange box 12:00 – Pumpkin Pics (Giant Mickey Pumpkin photo spot) – green box 1:30 – Mark Twain Riverboat (ride together & take pics) – teal box 5:30 – Scavenger Hunt Buttons (in line for Castle Photo Pass) – purple box Group Castle Pic (Castle Photo Pass spot) – black box Bottom corner features a white pumpkin with Mickey ears, bow, and flowers that reads “Main Street Pumpkin Day.”

Map graphic of Disneyland’s Main Street area highlighting the Kick Off & Goodie Bags meetup at 11:00 AM. The map labels buildings including Main Street Cinema, 20th Century Music Company, Main Street Magic Shop, Disney Showcase, The Mad Hatter, and The Disneyland Story presenting Great Moments with Mr. Lincoln. A large orange Mickey icon marks the location at the Opera House. Decorative border with pumpkins, flowers, vines, and a small ghost. Bottom corner shows the Main Street Pumpkin Day logo with Mickey ears and a white pumpkin.

Orange and white event graphic titled Kick Off & Goodie Bags. Decorative flourish separates the header from the details, which read: “Find your Ghostesses in the ❄️ air conditioned ❄️ gallery area of the Main Street Opera House. We’ll hand out goodie bags to the first 25 Pumpkin Day folks to arrive and scavenger hunt rules then watch Walt Disney – A Magical Life.”

Countdown to #MainStreetPumpkinDay 9/28/25 🖤🎃🖤🎃 This schedule will stay pinned and you can find more information at owlsociety.life/pumpkin-day-2025

#Disneyland #UnofficialDisneyDay #DressUp #Halloween #HalloweenTime #DisneyHalloween #DisneyAnaheimResort #California #MeetUp #SoCal #Disney

This right here is why our #MainStreetPumpkinDay event (and our mothership: @owlsociety.bsky.social) will ALWAYS be inclusive and accessibility-minded. Resistance with joy, folks!

A mom and daughter stand together in front of a stage in tomorrowland. One woman is wearing an orange top with a black skirt, striped stockings and holding a black and orange umbrella. The other is wearing a black and orange spider print dress and black tights.

A mom and daughter are posing in front of a stage in tomorrowland. The daughter is kissing her mom‘s cheek and the mom is smiling. They are wearing black and orange Halloween-themed outfits.

Mom & daughter bonding at #mainstreetpumpkinday 2024. Love to see it! 🖤🎃🖤

#love #family #moms #halloween #disney #disneyland #tomorrowland #dissky #disneysky #cute #joy

A group of five diverse women stand smiling, holding packages with prizes at Disneyland in California. They are wearing pumpkin and Halloween themed outfits.

Winners from last year’s scavenger hunts! Soon admin will be planning for the next #mainstreetpumpkinday Sept 28, 2025 🖤🎃🖤

#disneyland #halloween #disneyfriends #magickey #disneylandresortanaheim #dressupday #funwithfriends #disneysky #dissky

A diverse group of women ranging in age from late thirties to mid sixties are dressed in Halloween and pumpkin inspired outfits. They are grouped together.

Some of the @owlsociety.bsky.social admin & volunteers that made #mainstreetpumpkinday happen last year! I love these women so much! And I gotta say, when you come hang with us (and we welcome you!) the vibes are ✨immaculate✨ #DisSky #disneysky #oldwomen #beautiful #wisebabes #maidenmothercrone

Hiiiiii!!! I’ve been searching for my fellow Disney people! If you’re in Cali, I hope you join us for the next #mainstreetpumpkinday in September. I’m moving my communities off Meta so I don’t have info and posts here yet, but I will!

Fat, redheaded woman smiles broadly holding up an orange, pumpkin-shaped frame that reads “@mainstreetpumpkinday”.

Happy Thursday #Disneysky and all my spooky people. This is me fat, happy & STUNNING at #MainStreetPumpkinDay last year. What is that? It’s an annual, unofficial dress up day that I host at Disneyland (UNAFFILIATED!). Follow me to get details for this year. Inclusivity-minded event, all welcome!