Once the oversized dumpsters in the parking lot behind The Playhouse are moved to a better area, and there’s also a new ramp connecting that lot with the alley that runs alongside Le Pain Quotidien, enforcement officers will focus on getting double-parking delivery trucks off New Canaan’s main drag downtown.
As it is, delivery trucks exacerbate congestion on the one-way stretch of Elm Street throughout the day. That segment of Elm and the commercial block of South Avenue both will change to paid parking later this summer, reversing a decades-old system. (When that happens, the town will convert the paid spots in the Park Street Lot to free.)

Elm Street on May 20, 2025. Credit: Michael Dinan
“We are going to be trying to push them, and we do that now,” Parking Manager Stacy Miltenberg said Tuesday during a regular meeting of the Board of Selectmen, held at Town Hall and via videoconference.
She continued: “We try to move them. We try to direct them where we can. We know deliveries have to be made. It’s not that easy. But hopefully we can move them to the loading zone on South Avenue. Hopefully we can move them behind into The Playhouse area so they can utilize that. Will some trucks have to park on Main Street? They’re going to have to, but we’ll try to keep them as quick as possible.”
The comments came as the selectmen approved the annual fees for the “premium business permits” in the Park Street and Morse Court lots for next fiscal year. (On the recommendation of the Parking Commission, they will remain at $582.77. Also, the Locust Avenue, Center School and Richmond Hill lots will remain free to all employees of businesses in town, following a 3-0 vote from First Selectman Dionna Carlson and Selectmen Steve Karl and Amy Murphy Carroll.)
Town officials last month approved funds to purchase nine paid-parking machines, seven for Elm Street and two for South. Members of the Parking Commission this month pushed back on part of the overall proposal—namely, to eliminate, rather than increase, the number of designated 15-minute free parking spots on Elm.
The change to paid parking on Elm and new free spots in Park Street Lot are expected to help ease traffic congestion downtown and free up the coveted on-street spaces. Along with that, the town is reconfiguring the dumpsters behind the Playhouse in order to allow delivery trucks to park there.
Yet it’s unclear whether the newly configured Playhouse Lot will accommodate larger tractor-trailer trucks.
Public Works Director Tiger Mann said that FedEx, Amazon and UPS trucks should be able to use the lot with no problems but the town will need to “run some truck-turning templates” for larger delivery vehicles.
Tractor-trailers likely will not be able to use the lot, he said.
Parking enforcement officer Michael McCargo, a guest at the meeting, was called to address the Board when Carlson asked about which trucks likely would continue to park on Elm Street even after the change.
She asked specifically about Baldor’s food delivery trucks.
According to McCargo, Baldor surprisingly “is one of our better” vendors.
“They follow the rules,” he said. “They try to get here early.”
Yet Baldor trucks may be too large for the Playhouse lot.
McCargo said some companies, such as UPS, may be “willing to take the ticket” for double-parking on Elm.
Carlson responded, “Then that’s nice revenue for us.”
McCargo added that the loading zone located on South Avenue just off of Elm Street should be made bigger to accommodate large trucks.
I applaud all these parking and loading zones efforts to make things better on South and Elm Street and take the best outcomes going forward. They are needed to keep the downtown business area healthy. Good thinking on Main Street and newly developed Burtis Ave is also needed.