It was a cloudy day across Middletown, Conn., last Saturday.

The city of 47,000 is nestled in the Lower Connecticut River Valley and is the 20th largest of the state’s 169 towns.

It is also the home of one of state’s youngest and largest Pride festivals, with more than 25,000 celebrants coming to town last weekend to have fun. Many of those celebrants stood along Main Street, with the Pride March making its grand promenade.

At the front, just behind the organizers and their banner, a red Ford Mustang rolled amidst the swirl of fun and color. Astride the back seats were the Grand Marshals.

One of them was Hella Swagg, chosen for her community service work in addition to being a headliner among Connecticut’s talented — and underrated — drag scene. Three queens of the state put up their best glam on this recent season of RuPaul’s Drag Race.

Me? Grand Marshal? Really? YES!

The other Grand Marshal was a Black transgender woman who thus far in 2023 saw her work with Outsports nominated for a GLAAD award, was the subject of a documentary short on her work with Trans Lifeline, hosted a podcast, and scored two touchdowns on the season.

She was me. And I never thought I’d be in such a setting or hold such a title.

As I waved to the crowds along the streets, my mind thought of a dear mentor and friend.

She saw this coming.

My first Pride. Northhampton, Mass. 2013

Ten years ago

In 2013 I went to my first Pride where I wasn’t cloaked with a press pass. It was Northampton, Mass., Pride Weekend that first Saturday in May. A fun time in small queer-friendly town that throws a big gathering.

At the time I was a year into an exploration into exactly where my gender identity and my orientation were. I had been a member of a local support group then. A community was growing around me, and I was taking the first tentative steps forward. In the parlance of trans community slang, “the egg was cracking.”

I was at that Pride in a blue jersey, a pair of rather-short shorts with a wig showing the hair I wish I had at the time.

One of those at the epicenter was the head of the support group. A proud trans woman in her sixties with a jovial, dry sense of humor mixed with military-grade bluntness named Janis Booth.

My mentor and I: Janis Booth saw all this coming

One of the remarkable things about her: If an idea was in her head, it would certainly come out of her mouth. Booth, along with a group of older trans people like her, wore out a lot of shoe leather and wore out a lot of ears in Connecticut’s General Assembly. Their efforts were essential toward trans rights provisions becoming of the state’s human rights law in 2011.

I’ll never forget my first meeting with this group. I was already nervous as I walked in some 30 minutes late after sitting in my car, trying to work up the courage.

Her first words to me: “Hi! You’re late! Sit down, kid!”

She said it with a big, welcoming smile on her face. She was one of many who became close friends in the years since who took me under their wing.

That same sunny day at that Pride she took me aside and said:

“I don’t know where your journey may lead you, but I see something in you. No matter where it goes along the way, I see you helping a lot of people.”

Four years after she said this, I had come out to myself in full and was living as such. That same year — 2017 — my mentor and friend had a massive stroke. She died a few days after falling ill.

I drew a lot of wisdom from her, but one thing she told me long ago stood out: “You have to be out in the world to let people know that you are in the world.”

What a difference a decade makes!

The Power of Pride

Wednesday February 22, 2023. On that day Mississippi and Indiana had moved affirming care bans forward. The epic vow of Nebraska state senator Michelle Cavanaugh — that she would “burn the legislative session to the ground” to stop anti-trans legislation — would come the next day.

In my email I received the following: “Good Morning, Karleigh! On behalf of the partners of Middletown Pride—a collaboration between the City of Middletown, the Middlesex County Chamber of Commerce, Wesleyan University and the Russell Library—I am thrilled and honored to invite you to be one of our Grand Marshals for our 5th Annual Middletown PrideFEST!”

My first thought? Monty Python. “Spam. Spam. Spam. Spam.”

Two more insistent emails from Middletown Pride founder Christopher Forte confirmed that this wasn’t spam. They really wanted me as a Grand Marshal. Forte and others told me that when my name came up, and after a panel said I was part of during last year’s Pride, it was a “no brainer.”

Last Saturday was powerful, beautiful and at the same time humbling. I’m no elected official like my good friend Raven Matherne, Connecticut’s first out trans elected official and a Grand Marshal at this Pride in 2019.

I’m not at advocate at anywhere near the level of Monica Roberts, Raquel Willis or Hope Giselle. As a journalist, I’m no LZ Granderson by any stretch.

As a weekend athlete? I do my best, but if you put me in a race with CeCé Telfer, you better spot me at least 25 meters.

Yet in that week leading up to Pride I saw my impact. The NBC Connecticut interviewer who told me “I looked you up. You do a lot!”

The pregame kiki at my co-Grand Marshal’s apartment, along with a lot of friends and Hella telling me, “Girl, you inspire me to do more. You are powerful and you need to know that!”

Leading up to the start of the march. I was doing a pregame on Facebook Live with all the groups assembling and getting ready to march down Main Street. I saw people I had never met, many of whom heard me speak at the flag-raising ceremony in town a few days before, telling me how much they valued me and saw me as a powerful inspiration.

My whirlwind Pride week in pictures

There was also the added spark of people liking my outfit for the day: a pink football jersey done in a white-blue trim, powder blue skirt, with thigh-high socks done in perfect trans pride formation (thanks, Sock Dreams).

It was a version of a similar outfit I wore to a Pride event last year, which ended up bringing me back to football as a player.

Hearing “KARLEIGH! KARLEIGH!” as the convertible rolled down Main Street was special and humbling just the same. I couldn’t stop smiling, laughing and taking in the wonder of it all.

The feeling hit me hardest just before my time to address the crowds after the march at main stage erected along Middletown’s main green. Thousands were settling in awaiting the performers to come.

I was hearing Hella and Forte introducing little ol’ me.

I looked up and said softly, “Janis, you called it.”

I skipped up the plankway to the stage, and when Hella handing me the microphone, my first words were: “IT’S GREAT TO BE AT MIDDLETOWN PRIDE!”

Addressing the crowd at Pride. I didn’t see this moment coming 10 years ago, but those who embraced me did, including my late mentor

As I write this, removed from beauty of the moment, I’m still processing a lot of emotion. What I saw and felt last Saturday is the power of Pride.

There are the yearly debates about the place of Pride in our individual journeys and the struggle for our rights. There are continuing debates over how Pride has been homogenized and corporatized. Pride 2023 comes amid a nasty anti-LGBTQ legislative backlash across the nation and in many parts of the world.

However, let us all consider how we can positively impact someone else. A kind word, a nod of recognition, even a “I love your outfit” can plant a seed, especially to those who may be at their first Pride scared, unsure and questioning.

I am grateful to everyone who took that time for me when I was scared, unsure, and questioning a decade ago. You helped me be out in the world, and together we continue to impact it.

That is the power of Pride.