One of New Canaan’s best-loved community events, May Fair at St. Mark’s, is coming Friday, May 8 and Saturday, May 9 (there’s also a White Elephant tag sale preview party on May 7).
There are opportunities to volunteer and donate to the hugely popular White Elephant tag sale. (All May Fair details can be found here.)

John Kennedy Jr. planning for this year’s May Fair, to be held May 8-9, 2026. Credit: Michael Dinan
We talked to event Chair John Kennedy Jr. this week about this year’s May Fair.
Here’s a transcript of our conversation.
***
New Canaanite: Would you please give our readers a little bit of background about the May Fair, and then we’ll talk a little bit about how this is all coming together since we’re just a few weeks away.
May Fair 2025. Credit: Michael Dinan
John Kennedy, Jr.: May Fair started 77 years ago and it was known as the ‘Strawberry Festival’ initially and then was transferred to ‘May Fair’ probably I think in the ‘70s. And then I think in the late-’70s they started having rides. So it started with just some little White Elephant things and then having the access to the great lawn allowed them to create a midway for rides. And then maybe 10 years ago, they started with that ‘Friday Night Lights’ program. And that was a big addition.
That was a big change. And maybe the biggest recent change to May Fair. As someone who grew up here and went to May Fair and continues to come back, it seems like it just appears and then it’s gone. The midway is clean beforehand, and it’s pristine afterwards. But there’s a lot that goes on behind the scenes. So give us a peek behind the scenes. What is something that happens in the planning that a lot of people probably would underestimate or wouldn’t know about?
May Fair 2025. Credit: Michael Dinan
We have an executive committee of 12 people now, each of them have a variety of tasks and it starts pretty much after May Fair. So probably the week after the fair, we kind of download information and get some feedback from our department heads. So there’s a lot of absorbing of information after-the-fact. And then you meet again starting in the fall. I would say probably the committee spends a dozen hours in meetings after May Fair and during the fall, to get things laid out, identify new department chairs. And then obviously for the two months before, they probably spend 40, 60 hours [per week].
What are the discussions like around here with all this unpredictable weather we’re having as the date nears?
May Fair 2025. Credit: Michael Dinan
Oh, the weather. I said to my daughter that I can do all the planning in the world and if the weather’s not good, it won’t be a great May Fair in terms of attendance. But I could do a terrible job planning and if you get perfect weather, May Fair will be great.
Although, John, I remember last year talking to you and it was a beautiful Saturday, but the Friday Night Lights was a little tricky. And you said there were still young people that came out for that.
It started out being cool and a little drizzly. So the kids are going to come and they planned on it. And then the weather got very poor around eight o’clock and we had to shut some of the rides down.
May Fair 2025. Credit: Michael Dinan
What would you tell some of those people who are reading this about what they’re going to experience?
We’ll talk about Friday first. I would say if you’re over the age of 10, just the energy, many attendees come with friends— the lights come on when it’s dark and then the rides, the excitement, they can pop down and get pizza. Get some ice cream. There are a lot of plusses to it. I’ve spoken to people who have been members of the community for many years—for example, Richard Westfall, whose children were great athletes, when I was talking to him about a month ago, about something separate, he just said, ‘I was talking to my kids and they said that’s one of their fondest memories of New Canaan, is May Fair.’ And then on the Saturday side it’s just the whole family part where they can bring younger children and be with their parents. And the parents can see the kids doing something that otherwise they wouldn’t be able to do.
May Fair 2025. Credit: Michael Dinan
Is there anything new or special that you’d like to spotlight that’s on the agenda for this year’s May Fair?
There are two new programs. We’ve created a theme, which is called ‘Gathered In Joy.’ And that’s the headline. And so we created two new programs, one of which is we’re working with HHS [the Department of Health & Human Services] in town to identify 10 to 12 families that otherwise couldn’t afford to come to May Fair. And so we’ve had some generous donations and we’re going to provide tickets and food vouchers for those dozen families. And then secondarily, there’s a group in town called Inclusive Together that a lady named Lauren Tarzia runs for children who are neurodiverse. And so we’ve created a safe space for them where they can attend the fair and then find a little half-hour getaway. Because May Fair is primarily a community event as a fundraiser, so we can take those funds and give them to other charitable organizations in the area. And we’re trying to grow that concept of it’s not just about raising money. It’s really about making people feel welcome.
May Fair 2025. Credit: Michael Dinan
Let’s talk about that for a second. Some people may not realize it’s a fundraiser and the funds that are raised go to charitable organizations, and that must be a whole other process for St. Mark’s to vet. And I don’t know if you take applications or how this works, but that’s got to be its own separate involved process for you.
I’m not involved in that, but they do have an outreach commission where they have, I think, six or eight parishioners who accept applications from different nonprofits and charities and decide what portion of the funds they’re going to give them. It’s great.
May Fair 2025. Credit: Michael Dinan
Let’s talk about some of the nuts and bolts of May Fair. It runs from what time to what time on Friday and Saturday and where should people park? What sort of transportation services, if any, are available and what should people bring? Is there anything they should be doing in advance?
Friday night we open ticket sales at 4 p.m. The midway opens at 5 p.m. and it runs till 10 p.m. The food court is open at 5 p.m. on Friday night and runs till 8 o’clock, so families can count on coming a little bit early to beat the lines. Friday night, you get a wristband for $35, so that gives you access to all the rides on unlimited use. And they can count on having dinner here because the food court—the food court has a pretty good selection of foods, it’s not just pizza—you have pizza and hamburgers, you’ve got pulled pork and this year they’re gonna have grilled chicken, so that’ll be a nice addition. And as far as getting here, they park at the Lumberyard big parking lot in town. And GetAbout will have a couple of vans, which will be rotating people and dropping them up on, on Oenoke right across the street and their policemen there to guide them across the road safely, and then they can enter the park. There’s two ticket booths, and they can either pay by cash or credit card.
May Fair 2025. Credit: Michael Dinan
That’s for tickets for the rides and games. You get food separately with cash, right?
The food is down in a separate food court and you can pay either by cash or credit card down there. And then Saturday, we start at 9 a.m., they open up the White Elephant [Tag Sale] at 9 o’clock. The midway opens at 9 o’clock. So everything is pretty much a go. Food court opens at 10:30 a.m. and food courts open till 3 p.m. White Elephant is open till 3 p.m., but the midway’s open until 6 p.m. and Saturday are tickets, not the bands. So you buy blocks of tickets and each ride is three to five tickets to get on. And we have other activities on Saturday, too. They’ve got the Old Faithful [fire engine], which drives up. The pickup is on Oenoke Ridge right across from the street from the church. You’ve got the Town Band playing at 11:30 a.m. The Pivot Ministries sings at 12:30 p.m. and at 1:30 p.m. we have a dog show. So people are welcome to bring their dogs and be in the competition. And then probably one of the favorite things of the May Fair, which I didn’t get to participate in last year, is the strawberry shortcake. They always run out, so people love that. And they have it both Friday evening and Saturday.
May Fair 2025. Credit: Michael Dinan
Is there anything else you’d like to say about May Fair before I let you go get back to the planet?
I think it’s a great opportunity for people to spend time with their families. People are welcome to volunteer even if they’re not members of St. Mark’s. So they just go to the St. Mark’s website. There’s a May Fair page and there’s a QR code where if they want to come one day and help out we’ve got people from other churches who are helping volunteer. We’ve got the SLOBs, which is the group from the high school, volunteering. The Boy Scouts. So again, there’s a lot of diverse groups which are not St. Mark’s, but they’re all part of that program. So you can either be a volunteer or you can have fun, or you can do both.
Are there any pressing areas for organizers right now in terms of volunteers or donations?
I think it would be great if people understand that the White Elephant donations obviously translate to dollars for charity. Start going through your house, things that you don’t want. Again, you can go to the May Fair page and find out what we accept and don’t accept.