Editorial: My First May Fair ‘Date’ [PHOTOS]

May Fair 2025

It was Eric Rehnberg who crossed over most successfully in third grade, our first year at East School. They’d closed Center School after the 1982-83 academic year, and our friend group got separated in the redistricting, never to fully re-form. Eric and I ended up at East, along with Alex Carles, Kristen Gannalo, David Palmer, Linda Pierson, Christina Mullin and Jenny Rubinfeld.

Somehow that first year at East, Eric found the courage to ask the cutest girl in our class, a new face to us Center Schoolers—Joanna Avgerinos—to May Fair, and she said yes.

I was in awe. And as my academic career at East unfolded, it seemed like everyone else’s first date was May Fair. I pictured boys and girls meeting at the St. Mark’s Episcopalian Church midway, buckling up side-by-side on rides, eating cotton candy together and—I allowed myself to imagine—holding hands.

***

The Rev. Peter Walsh, pastor at St. Mark’s, once told me that the way May Fair comes together each year is “tribal,” a reference to the individual groups that must coalesce to pull it off: The Holy Smokers, White Elephant tag sale organizers, police, strawberry shortcake team and those responsible for sponsorships, rides and games.

This past weekend, those hundreds of volunteers—once again—pulled it off in style.

Here’s what this year’s May Fair Executive Committee chair, John Kennedy, Jr., told me during an interview just as things wound down on a sunny Saturday afternoon: “It was amazing. We went through a great Friday night. Despite the rain, the spirit was great. Probably 75 percent of the children showed up and had a great time. No injuries, nobody yelling at each other that we saw. And today was very special. The sun was shining and we had the spirit of Pivot Ministries singing for us, and the Town Band. And we also had the ‘Inclusion Tent,’ which was great for the kids who need a little quiet time. So it was a great two days here at St. Mark’s.”

Committee member Eric Thunem, interviewed at the public address tent, was similarly enthusiastic when asked how it went: “We lucked out with the weather. A little chilly this morning, but the sun came out and for the entire afternoon, it’s just been spectacular. And I was just saying to Mark Thorsheim, it’s incredible how smooth today has been.”

Fairgoers clutching blue and orange tickets waited in lines for favorite rides like the Cliffhanger and Skyhawk, shot water guns and tossed bean bags for prizes, munched on candy apples and shaved-ice snow cones, and greeted each other with wide smiles.

Holding dog leashes and little kids’ hands, parents and grandparents took photos and videos of smiling children—none smiling more brightly than my first May Fair date.

***

My niece Dillon is eight years old and this was her first May Fair. She put on a ribbed pink tank top, white shorts and Timberland boots (the midway was muddy after a rain-soaked Friday Night Lights), and brought a light pink fanny pack.

Dillon—or “D,” as she’s known here at my sister Rachel’s house in Weston, where I’ve been living for the last three-plus months during a time of change in my own life—is a sweet, sensitive girl who is admiringly referred to as “a little diva” at times.

For example, one recent weekday morning I saw her in the kitchen before school.

“Someone’s rocking a skirt today,” I said.

No response. I tried again. She was wearing a yellow baseball cap with a white turtle printed on it.

“I like your turtle hat,” I said.

Dillon turned to me and said without expression, “Then you should have said something sooner because I’ve been wearing this all week.” And walked away.

We arrived at May Fair during its height—about 1 p.m. Saturday—and as we moved through the crowds I saw many of the friendly smiling faces that always make me happy to be in New Canaan: Miki Porta, Eric Thunem, Robin Bates-Mason, Joey Mysogland, Joe Farenga and Katie Owsley. My brother Terry came through with his wife Andrea, their son Cooper and Emmy, a sweetheart goldendoodle.

D wanted cotton candy on a stick, so we got one. She told me it was the wrong color (pink), so I exchanged it for the right color (blue). (Again, thank you for that, cotton candy workers.)

After four rides, Dillon said she wanted to win a prize and we headed to the games area ($5 per go), where she fell short at the Ring Toss and Whack-A-Mole. She then tried three times to knock down a pyramid of metal cubes with bean bags.

After the third try, I told Dillon I was running out of cash (true).

“It’s OK Uncle Mike, when you run out of money, I can use my own,” she told me. That explained the fanny pack.

And she did, casually pulling out a wad of cash for a ball toss game. She won two stuffed-animal turtles and a toy trumpet, then dropped $20 for a beautiful henna pattern on her right arm, finished in green sparkles. It was her favorite part of the day, which made it my favorite part of the day.

D said she had to keep it completely dry for 30 minutes, and handed me her water bottle, two turtles, trumpet and fanny pack, which I dutifully carried around for the rest of May Fair.

***

May Fair is one of those defining community events that marks time for people like me who grew up in New Canaan. When we were little kids on Parade Hill Road, Terry would lead me and Rachel on a walk up Hampton Lane to Oenoke Ridge to the fair—a route that my brother, a Parade Hill Road resident, re-traced with his own kids through their childhood years.

As a reporter, May Fair is a good event to cover—lots of photos and a quick quote or two, like covering the Family Fourth at Waveny, the Sidewalk Sale or Caffeine & Carburetors.

That’s what I’d planned to do, but when we got back to Weston, Rachel told me I should write about going to May Fair with Dillon (a third-grader). I’m glad she did. As with other things that I’ve been through this past year or so, I can see now that I just needed to be patient, and that my first May Fair date would arrive right on time.