End of Summer Ms Main Street Bash Gala & Pin Up Pageant
Part of the End of Summer Main Street Bash! Saturday, September 12, 2026 • Historic Downtown Ashland, Ohio
This Isn’t Just a Pageant… It’s an Experience.
The Ms. Main Street Bash Vintage Pin Up Gala & Pageant is one of the featured experiences of the End of Summer Main Street Bash.
As historic downtown Ashland comes alive with beautiful vehicles of every era, custom builds, motorcycles, local businesses, live entertainment, and thousands of spectators, sixteen selected Pin Ups become part of the celebration itself.
This isn’t about spending a few minutes on stage.
It’s about spending the day immersed in one of Ashland’s most unique annual celebrations… making new friends, supporting our downtown businesses, interacting with spectators, celebrating vintage style, and becoming part of the story that fills Main Street each September.
For one unforgettable day…
YOU are part of the show!!
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2026 Theme — Hello Autumn
As summer comes to a close, downtown Ashland begins transforming into one of Ohio’s most charming small towns. Patriotic decorations give way to beautiful autumn colors as the community welcomes the changing of the seasons.
Our 2026 theme is “Hello Autumn.”
Think warm colors, timeless elegance, harvest charm, and celebrating the beauty of the season.
Although many of us love bats, spooky season, and Halloween (myself included), this year’s theme is about welcoming Autumn—not Halloween.
Contestants are encouraged to embrace the warmth and charm of the season while staying true to the classic vintage pin up aesthetic.
Attire should represent styles from the 1920s through the 1960s. Rockabilly and artistic interpretations are welcome. Clothing does not have to be authentic vintage.
Bathing suits, lingerie, and Halloween costumes are not permitted.
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Your Gala Experience
If selected as one of this year’s 16 Pin Ups, you’ll spend the afternoon as one of the featured faces of the End of Summer Main Street Bash.
Throughout the day you’ll meet spectators, interact with fellow Pin Ups, visit local businesses, pose for photographs, and become part of the experience that thousands of people come downtown to enjoy.
This isn’t simply a pageant…
It’s a Gala.
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Special Meet & Greet
Before the festivities begin, you’ll take part in a special Meet & Greet where you’ll have the opportunity to meet fellow Pin Ups, photographers, spectators, and members of our downtown community.
More exciting details about this year’s Meet & Greet will be announced soon… and trust me, I think you’re going to love what’s in the works!
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Limited Edition Trading Cards
One of the signature traditions of the Gala!
Each selected Pin Up will receive a custom set of professionally designed, limited-edition trading cards featuring the photograph submitted with your application.
These cards are yours to autograph and share throughout the day with spectators, car show participants, families, and collectors.
Years from now, I hope someone finds one of your trading cards tucked away in a keepsake box and remembers the incredible day they met you in downtown Ashland.
Pin Up Pit Stop Tour
One of the absolute highlights of the day!
As part of the Gala, you’ll take part in our exclusive Pin Up Pit Stop Tour, visiting several locally owned downtown businesses.
This isn’t about shopping.
It’s about our downtown businesses welcoming the Gala of Pin Ups into our community.
Many of our participating businesses prepare special gifts, treats, or goodie bags exclusively for our Pin Ups as a thank-you for helping make this event so special.
Along the way you’ll interact with spectators, pose with beautiful vehicles, visit with business owners, and experience downtown Ashland in a way very few people ever do.
It’s truly a one-of-a-kind experience.
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Photography
Throughout the day you may be photographed by event photographers, magazines, sponsors, vehicle owners, spectators, and members of the media.
Please remember that you are representing both yourself and the Gala throughout the day.
We encourage classy, tasteful vintage photography and ask contestants to refrain from inappropriate or overly suggestive poses while attending the event.
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Gala & Pageant
The day concludes with our on-stage Gala & Pageant presentation.
This is where our panel of judges will recognize the ladies who have truly embraced the spirit of the Gala.
Judging isn’t based solely on stage presence.
Throughout the afternoon our judges will also be observing personality, sportsmanship, crowd interaction, kindness, overall presentation, and how each Pin Up represents both herself and the event.
Because at the end of the day…
This experience is about so much more than walking across a stage.
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Awards & Recognition
Five ladies will be recognized during this year’s Gala.
The official award categories will be announced soon.
Each category winner will receive a custom title sash, with cash prizes awarded to our overall winners.
1st Place — $500
2nd Place — $300
3rd Place — $200
Additional specialty awards and recognitions will be announced as the event approaches.
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Our Expectations
This event is built on kindness, encouragement, community, and respect.
Women of all backgrounds, body types, ethnicities, experience levels, and hometowns are welcome and encouraged to apply.
Whether this is your very first pageant or you’ve participated in many over the years, our goal is simple:
We want every Pin Up to feel welcomed, celebrated, empowered, and leave with memories they’ll carry long after the day is over.
Bullying, harassment, name-calling, or negative behavior toward fellow contestants, volunteers, businesses, judges, spectators, or event staff—whether in person or online—will not be tolerated and may result in immediate disqualification.
This is a family-friendly event.
Profanity, political discussions, current events, or controversial topics have no place on stage or while representing the Gala.
Please help us create the positive experience that has become one of the hallmarks of this event.
Supporting a Cause
One of my favorite parts of this Gala is that together we’re able to give back.
This year’s proceeds will benefit the National Niemann-Pick Disease Foundation (NNPDF) in honor of eight-year-old Officer Allysson Nead, who is courageously battling Niemann-Pick Type C.
As part of the application process, applicants will be asked to make a $20 donation directly to this year’s selected nonprofit.
Your application will be considered complete once both your application and proof of your donation have been received.
Every dollar goes directly to the nonprofit.
Your donation doesn’t simply enter you into the Gala…
It helps create an unforgettable experience while giving back to an incredible cause.
Important Information
Applicants must be 21 years of age or older.
• Application deadline has been extended to 1:00 PM (EST) on August 7, 2026. (Due to a Meta error delaying posts)
• Submission of an application and donation does not guarantee selection.
• Our judging panel will carefully review every application before selecting the 16 official Pin Ups for this year’s Gala.
Selecting only sixteen ladies is never easy and is one of the most difficult parts of organizing this event.
Those selected will receive notification approximately 24 hours before the official public announcement.
• Please be aware of social media scammers.
Kandi Blaze (Kandi McCrea) is the official host and producer of the Ms. Main Street Bash Vintage Pin Up Gala & Pageant and the only individual accepting applications for this portion of the event.