PHOTOS: May Fair 2023

Thousands of residents and families made their way to the St. Mark’s Episcopalian Church midway on Friday night and Saturday to enjoy May Fair. One of New Canaan’s favorite community traditions, the annual fair features dozens of rides, delicious food from the church’s Holy Smokers, White Elephant tag sale shopping and other fun—with all net proceeds supporting St. Mark’s outreach ministries and grants to other nonprofits serving those in need. (For a full list of recipients, visit the May Fair Website.)

“May Fair is a great demonstration of what the community can do when it comes together and the Good Lord provides the weather,” Co-Chair David Shea told

Q&A: May Fair Set for May 12-13

One of New Canaan’s best-loved community events, May Fair, is scheduled for Friday, May 12 and Saturday, May 13. We put some questions to event Co-Chair David Shea, and our exchange follows. (Note: The New Canaan High School Service League of Boys or “SLOBs” are volunteering prior to the event in collecting donations and will partner during May Fair with Planet New Canaan to ensure that proper receptacles are being used for recycling and composting.)

How would you describe May Fair to someone who’s never been to it? 

David Shea: May Fair is a much anticipated two-day event that’s now in its 74th year and established New Canaan tradition. May Fair kicks off on Friday, May 12th (5 to 9 p.m.) with Friday Night Lights. We will have all 20 amusement rides open as well as the food court serving a delicious range of options from favorites like Holy Smokers barbecue, corn on the cob, our signature Strawberry Shortcake and pizza.

‘Have Fun While Doing Good’: May Fair Organizers Call for Volunteers

Volunteers are needed to help run one of New Canaan’s most treasured community events, officials say. The organizers of May Fair say about 200 volunteers are needed to fill what are typically two-hour shifts on the evening of Friday, May 6 and in the morning and afternoon of Saturday, May 7. (Sign up here.)

“This is an opportunity to re-engage with the community, meet new neighbors and new friends, and contribute toward the worthy cause of helping our outreach mission reach many, many needy charities in Fairfield County,” May Fair co-chair David Shea said. “Have fun while doing good.”

Walkable for many from downtown New Canaan, the family-friendly May Fair features rides, games, food, live music, a massive tag sale and the best strawberry shortcake around, among other attractions. (Here’s a podcast with Shea about May Fair 2022.)

Some 425 volunteers are needed to run May Fair, and as of Tuesday afternoon 231 had signed up, he said.

Podcast: ‘May Fair’ Returns in 2022

This week on 0684-Radi0, our free podcast (subscribe here in the iTunes Store), we talk to David Shea, who serves as co-chair of May Fair (see video embedded below), along with “Holy Smoker” George Wright. After two years of cancellations due to the pandemic, the hugely popular May Fair is back on—scheduled for Friday, May 6th (4 to 9 p.m.) and Saturday May 7th (9 a.m. to 6 p.m.). We talk to David about what May Fair’s all about, including the organizations that benefit from it, what goes into organizing May Fair, what’s on offer this year and also, ways that organizers are introducing new features for New Canaan’s growing community of young families. 

We also note here that nearly 400 volunteers are needed to put on the May Fair and there are slots open—those who are interested can call the St. Mark’s church office 203-966-4515 or email In addition, donations for the May Fair tag sale are welcome, they’re taking drop-offs at the church house of toys, art work, jewelry and find goods, and people may call in for pickups of furniture and housewares.

‘A Pattern of Abuse’: Police Commission To Remove Auto Shop’s Designated Parking Space on East Maple Street

The volunteers who oversee on-street parking in New Canaan voted last week to spend $1,700 for a field analysis and sight line study of East Maple Street, an increasingly busy commercial area downtown whose residents say they’re concerned about traffic and safety. At its regular meeting Wednesday, the Police Commission also decided to discontinue a practice whereby an auto body shop on the corner at Main Street is allowed to park on East Maple. Instead, the commissioners said, AC Auto Body will use two designated spaces in the nearby Center School parking lot for its flatbed trucks and could park a smaller wrecker in its own lot. East Maple Street resident David Shea, who has become a spokesperson for the concerned neighbors, told the commission at its July 20 meeting that “what we are looking at is two kinds of streets when you come up East Maple from Hoyt it is a wide street.”

“As you turn in the curb toward Main it becomes a bottleneck, it narrows down,” Shea said at the meeting, held in the New Canaan Police Department’s training room. “What we are proposing is that parking only be on the right-hand side of the street, the usual two hours, and then on the right-hand side going east, that would be no-parking, no-standing [zone] that will allow traffic to pass on a two-way basis and give the residents the parking that they need.