Pinkfest Chicago 2019 — Part 1

| Nov 11, 2019
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After months of planning and trying to get the word out, Pinkfest 2019 finally arrived and from my perspective was a huge success. The only downside was that as an organizer, the week went by way too fast — not enough time to just enjoy being Julie.

If you’re not familiar with Pinkfest, it’s basically a week of activities all around Chicago. Some activities are ‘safe space,’ either in Boystown or queer friendly venues, but a good portion are just regular ‘mainstream’ activities. If you’re interested in the detailed schedule for 2019, you can look at it here. In summary, 2019 had 24 people attending from all over the country, including Chicago, Milwaukee, Green Bay, St Louis, Toronto, Austin, Las Vegas and Los Angeles. 

Tuesday Daytime:

The first activity of 2019 was on a Tuesday, which was lunch on the patio of a Boystown restaurant called DS Tequila. I had taken the day off of work and was able to get an extra early checkin at my hotel so I could get my Julie on and make it to lunch by 12:30. By the way, I live in Chicago, but usually get a in town hotel room for changing — I’m not out to my kids, so it’s a bit of a necessity. So, with the extra early checkin and a bit of rushing, I was out the door and walking to the restaurant by 12:15. I was expecting to meet up with Dee, Brandy and Nancy, but when I arrived I was surprised to find Erica and Ajay waiting for the group — neither had rsvp’d, which is fine cuz Pinkfest is relaxed about the whole rsvp thing. By the way, did I mention that Pinkfest has no registration fees? Yeah, it’s true and how we like it. Eventually, the other 3 arrived and we had a wonderful lunch with everyone getting to know each other — most were meeting for the first time. After lunch we all went across the street to Beatnix, a drag/costume shop, where Brandy and I found some bracelets that fit our larger than usual wrists. The 6 of us then hopped on a CTA bus to Clark & Diversey for some more serious shopping at AKIRA — an awesome Midwest chain store focusing on club wear. Dee tried on several dresses, but didn’t find anything she liked. I, on the other hand, found this great black skirt that’s covered in a netting of rhinestones, along with a rust colored top. Wasn’t sure about the combination, but as soon as I tried it on I was floored, “OMG!! I need to wear this tonight.” So, after a little haggling over the price with the sales girl (who happened to also be trans), I was a very happy girl and oh so ready for the evening’s activities. After a quick stop at Trader Joe’s for everyone to use the little girl’s room, we decided to walk it back to Boystown, where most of us had our hotel rooms. Although, we did stop off for a late afternoon drink at Shakers where we had our first toast of the week. 

Tuesday Evening:

After an outfit change, I met up with Brandy, Nancy and Ajay and we headed out to the Kit Kat Club, our initial meeting place for the Taste of Boystown, and waited for Dee and Sandy to arrive. While the rest of us were goofing off all afternoon, Sandy was busy flying in from Austin, flying pretty no less, and was the only one that opted for the Wrigley Field tour, which is just a few blocks from Boystown. So, we spent the first part of the evening meandering through Boystown, getting food samples at a half a dozen restaurants — I, of course, got many compliments on my new web of diamonds skirt. After a couple hours of meandering, we made our way to The Annoyance Theater for some improv comedy. I was not all that impressed with the show, but it was only $6 and not unexpected for a Tuesday night. After the show, we walked a couple blocks to a club called Berlin, hopefully to find a little dancing, but instead found a weird birthday party going on — again I blame it on Tuesday night. With that being a bust, I suggested we catch an Uber to a place called the Hungry Brain, which has open mic jazz on Tuesday nights. As we were leaving Berlin, I heard someone say behind me, “that looks like the Pinkfest.” I’m like, who in the world would know that and turned to find Amanda in boy mode. She was just coming from the social activities that followed her trans support group meeting and thought she might find us at Berlin — perfect timing to join us for jazz. This Hungry Brain place is really awesome on Tuesday nights — all the musicians are from the audience and we were pretty much the only non-musicians in the place. About 1a.m we closed the place and made our way back to our hotels. For me, that meant deconstruction back to boy mode and getting home about 2:30 a.m. so I could go to work in the morning.


Wednesday morning, I went to the work meetings I was required to attend and knocked off early to get in a quick nap before the kids got home. My wife works Wednesday evenings so I was responsible for making dinner, which I did and got to bed early. I was gonna need the rest because I had 3 full days of Pinkfest coming up.

Thursday Afternoon:

On Thursday morning I kissed the kids goodbye (as far as they knew, I was heading out on a business trip) and after a quick re-shaving of my legs and face, I was out the door by 9 a.m., at my hotel in Boystown by 9:30 and ready to get my Julie on. I actually had to rush a bit, cuz I needed to be back on the train by 11:30 to make it to lunch in Chinatown by noon (yeah that’s right, it usually takes me about two hours to get my Julie on). 

Sandy was staying at my hotel and Danielle was at an AirBnB next door. Unfortunately, Danielle was running late, so Sandy and I hopped on the train without her. When we got to Chinatown, we immediately found Erica and Ajay waiting for us. As we approached the restaurant, Carrie showed up and Michelle arrived a few minutes later. We got a table and I noticed a group of waiters looking at us and it seemed they were negotiating about who was gonna serve us. Despite that initial reaction, the guy who did take our order was completely professional and treated us with utmost respect — in fact he even took our picture after the meal. Danielle arrived about 45 minutes late, but with super gorgeous makeup. I tried to complement her, but she said that she had hired someone to come in to give her a makeover, which was why she was late — that and getting lost off the train which put her under a viaduct with some homeless tents before turning back — never said that Pinkfest wouldn’t be an adventure. 

After lunch the 7 of us walked a few blocks to the river to catch the water taxi. Upon arrival we found Vivian waiting for us. She immediately pulled out her camera and declared herself as the official Pinkfest photographer. This was fine with me, cuz it turns out she was great at framing us for awesome pictures — and her camera is way better than my crappy iPhone 6. The water taxi ride was super chill with great views of the skyscrapers along the river. We got off at the river walk in the Loop and proceeded to take dozens of great pictures — the sun was out and plenty of building vistas in the background.

After a few pictures, I was getting antsy because I was the only one with naked fingernails. So, I cut out early, walked to the train and headed for my favorite nail salon — on Diversey just a few blocks from that AKIRA we went to on Tuesday. I’ve been to plenty of nail salons, but this one is the best because the nail techs are super friendly and always want to know about my outings and generally chat about everything from family life to shopping and makeup. After getting my 10 pretties taken care of, I headed back to my room for an outfit change. For lunch I was wearing my favorite skirt, blue and white with a white top, pearl necklace and earrings and black suede round toe heels. For the evening I changed to a super slinky green flower dress from Unique Vintage along with black, leather, pointy toe heels. In both cases, I had my sparkly flats in my purse for walking distances and riding on the train. 

After the outfit change, I met up with Sandy along with Danielle, who was hosting Michelle and Vivian at her AirBnB. The 5 of us were about to head to the train for the long ride to Rodgers Park when Vivian volunteered to order an Uber. It’s good thing she did, cuz just as we arrived at Phoebe’s wine shop, there were fire trucks amassing around the train station — the wine shop is just steps from the train station. Seems that someone ended up on the tracks and was hit by the train. It was a massive incident that held up tons of people on their afternoon commute. Brandy and Nancy got caught up in it and had to miss the wine tasting and dinner — we were lucky to have taken the Uber, else we would have been in the same boat. 

At the wine tasting we had myself, Danielle, Michelle, Sandy, Vivian, Ajay, Amanda (in girl mode this time), Elena and of course Phoebe who is a part owner of the shop and tells the greatest stories about each wine. Phoebe knows I’m not much of a wine drinker, so she encouraged me to make a selection from her spirits aisle. I pick out and bought some boutique vodka, which I still have and am drinking at this very moment. We then went next door to R Public house for dinner and some robust conversation. Just as we were leaving, the train accident was clearing up and we were able to catch the train to Kingston Mines for some awesome blues, where Brandy and Nancy were finally able to join us. While the blues club is totally mainstream with lots of tourists, no one gave us even a second look. This place is kinda unique in that they have two stages, so as one band is playing, the other is getting set up. The result is that there is always a band playing. We found some good seats in the room getting set up and after the first song they asked if we (the general audience) wanted to ‘groove’ or ‘dance’? I yelled out ‘groove!’ and they were like, okay she wants to groove. I asked Michelle if they were talking about me, and she was like, I think so. After a couple of songs they brought on the headline singer — an older African American woman. She slowly made her way up on the stage, looking very unsure on her feet. We all held our breath, hoping she would not stumble. Then, once the music started she came sprang to life and left us with no question about who owned that stage. Did I say I love this place! By the second set, I was done with grooving and was in my sparkly flats out on the dance floor. We didn’t close the place, cuz it’s open until 4 a.m., but we did stay until 1:30, and I finally got to bed about 2:30. Wow, that was a long day. Might need to take it a little slower on Friday and Saturday … not likely, but stay tuned to find out. . . .

Part 2 next month.

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About the Author ()

Julie Slowinski is a married crossdresser from Chicago who loves to make the most of her time en femme when she is out and about. She joins TGForum to share her adventures.

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