Key Points
- Wilton Pride issued a public call to action, claiming the Town denied its festival permit
- Town officials say the event was never denied, only the road closure request is under review
- Conflicting accounts stem from an application error and ongoing questions about the permitting process
Why It Matters: Conflicting accounts over what happened — and why — highlight gaps in communication, transparency and expectations between organizers and Town officials.
Organizers of Wilton Pride were very unhappy last week following what they said was a denial by Town officials to grant a permit for their upcoming Pride Festival, while Town officials said that the event was never in jeopardy and the issue may have been based more on misunderstanding and an application filing error centered on a request to close a Wilton Center street.
For the last three years, the nonprofit group has held a Pride event on the Town Green in Wilton Center that continues to grow in popularity. This year, they added a request that the town close off Old Ridgefield Rd. during the event on Sunday, May 31.
After being told their application could not be approved as submitted, in part because the original request listed an incorrect number of projected attendees, the group reacted with an “Urgent: Call to Action” urging residents to email Town officials to voice their concern, and reaching out to the media.
“Wilton Pride has been denied access to public space for our 4th Annual Pride Festival by Wilton’s First Selectperson, Toni Boucher,” the email to community members stated. “This decision threatens a community event that brings us all together and creates space for belonging.”
The alert was also posted on the group’s website.

The email to supporters provided a template letter for residents to use to contact both the Board of Selectmen and the Police Commission “to demand the immediate approval of the permits.”
Boucher, however, expressed support for the event and said that misinformation on the matter was being spread.
“This event was always to take place just [as] it has in the past,” she said. “The only question that is being considered is the organization’s request for the closure of the roads for the event.”
That was echoed by Deputy Police Chief Rob Cipolla, who said the group was never told it couldn’t hold its event.
“Nothing was ever denied. The question is, can we shut the road down? The original application indicated 100 people, and the priors year’s application indicated 50 [attendees]. So when the Chief [of Police Tom Conlan] spoke to them and said, ‘I can’t see shutting the road down for this size of an event,’ that then it was an error on their part, and now it was 1,000 attendees,” Cipolla explained.
He added that shutting a road down for pedestrian-only use takes a lot of resources.
“We want to ensure people are safe, and to do that, that’s resources — whether it’s us as the police and Wilton CERT, and a lot goes into that. So Wilton Pride’s festival has never been denied. It’s just been a discussion over whether the road can be shut down, and that’s what we’re still having discussions on,” Cipolla said.
Boucher said she has been in discussions with the town’s Emergency Management team on the matter, as well as reviewing the temporary event permit application process with each department that needs to sign off.
“We will have the information on additional resources and potential costs soon,” she said. “I am hopeful it will work out after we find out what additional public safety personnel may be needed.”
In fact, by Monday, Apr. 27, Boucher said she was hoping to have a final answer soon. “Waiting on emergency management but everyone else has signed off,” she said in an email to GOOD Morning Wilton.
By Wednesday afternoon (Apr. 29), Boucher reported even more promising news — and reinforced the Town’s ongoing support for the event.
“Police and fire departments are completing their review and a street closure request may require the of hiring of one or two security personnel for crowd safety now that the size stated on Wilton Pride’s original application has gone from 100 attendees to 1,000,” Boucher wrote to GMW. “We are also confirming that street crossing monitors are available. Once that this is confirmed and agreed to I will also sign off on the street closure. Again the Pride Festival was always going to take place. There was complete agreement on this. The only decision that was to be made was on street closure or no street closure.”
Questioning the Process
Resident Farah Masani, a founding member of Wilton Pride, was the primary contact with the Town during the application process, was she was identified by several Wilton Pride members as the group’s spokesperson this week.
Masani put together a lengthy, 15-page document outlining the series of events that began on Mar. 23 with Wilton Pride notifying Town Hall and the Wilton Police Department about its hope to have the street blocked off adjacent to the Town Green.
In the timeline, Masani noted that on Apr. 8 the town cashed a $500 deposit check from Wilton Pride, which she said was prematurely done.
“Typically, this deposit check is cashed when the permit is approved and returned 10 days after the event concludes if the property is returned in its original condition,” Masani wrote. “This check should not have been cashed if the application was denied.”
Two days later, she said, Police Chief Conlan denied the permit, citing that there weren’t enough people to warrant the closure, pointing to the 100 as the number of attendees listed on the application.
Masani said she sought to correct the mistake, emailing Conlan that “I see where the confusion seems to have stemmed from. This estimated attendees needs to say 1000 based on last year where we ended up with 1500 attendees. Clearly, I seemed to have missed a zero.” She also noted 30 vendors were planned at the time, and with activities, space beyond the Town Green was needed.
On Apr. 13, after following up, Masani said Conlan told her the permit was still “denied by Town Hall.”
Two days later Boucher wrote an email to Rev. Caroline Hughes of the Wilton Congregational Church, who was helping to organize the event, along with the Wilton Library, the Wilton Historical Society, and Marché, a Wilton-based marketplace business. [The Historical Society hosts a Food Truck Festival the same day in coordination with the Pride Festival.]
Boucher’s email to Hughes stated, “The town only closes the street for the annual Memorial Day Parade and the [Wilton] Chamber [of Commerce] sidewalk sale and not for other events.” The chamber’s Pumpkin Parade also runs with a street closure.
While Hughes was hopeful the matter would be resolved, she also raised questions about the process.
“I think the challenge for us has been in understanding why the Pride application was denied,” she said. “Did it not meet requirements, and what are the requirements?”
“I would love more transparency in this process,” Hughes said, “as I think that only makes us a healthier and more vibrant community. Fingers crossed we collaboratively work something out for May 31st.”
Jeffrey Busch, a founding member of Wilton Pride and longtime Wilton resident, likewise had some concerns about the process.
“The permitting process has felt unclear and inconsistent,” he said, questioning why some other events would warrant the road closure.
“Despite repeated requests for clarity, we didn’t even know for certain if we could hold the event on the Green until it was mentioned a few days ago in Toni’s monthly newsletter because she didn’t inform us of her decision directly,” Busch said.
For his part, Cipolla reiterated that from the Police Department’s perspective, it was never a question about the organization involved or whether the festival could take place, just whether the street closure was warranted.
“We’ve worked with Wilton Pride over the last three years with their 5K race… they start and end in Wilton Center. That requires a lot of logistics and resources, but we make it work. For this [Festival], they envisioned something different, and we’re reviewing it for this year,” he said.
And why does that take time?
“From our perspective, again, it’s public safety,” Cipolla said. “If we’re going to be shutting a road down, we want to make sure we’re doing it in a manner where we can keep vehicle traffic, pedestrians and festival goers safe. That’s our main priority, and our mission is to make sure we can keep people safe.”


