The parking problem
Why parking downtown feels hard
In an old downtown, parking went where it could fit: behind the shops, along the river, down side streets. The spaces are out of sight, so people circle Main Street.
- 20downtown lots
- ~1,500free spaces
- 8–6time limits, every day
Out of sight
The lots are behind the shops, along the river and down side streets. Parker Harding’s 213 spaces sit behind Main Street on the river. Baldwin is off Elm Street. Imperial Avenue’s 170 all-day spaces are across the river by the Levitt Pavilion, about a 15-minute walk from the middle of Main Street.
On a weekday at lunch the Main Street lots are usually tight. In the town’s 2024 counts, Imperial Avenue was less than a tenth full at the same hour. Drivers who don’t know the other lots circle Main Street.
How the rules changed
- Before 2020One- and two-hour limits on the street, with timed and all-day spaces in the lots.
- Spring 2020The town suspended time limits during the pandemic.
- May 1, 2024Limits returned: 3 hours in the lots and on the street, 8 AM to 6 PM, every day. The Westport Journal reported fines of $25 over 3 hours and $50 over 6.
- January 2025The town’s parking consultants suggested spreading parking out from the downtown core, with no parking deck for now.
- July 9, 2025The Local Traffic Authority voted for 2 hours on Main Street, Elm Street, Bay Street, Church Lane and Jesup Road.
- August 4, 2025The 2-hour signs went up.
The all-day squeeze
People who work downtown need all-day spaces. On weekdays the ones closest to Main Street, like Baldwin and the Jesup Road lots, fill first. In 2024 merchants told the Westport Journal they were full by about 9 AM most mornings.
Imperial Avenue, Town Hall, the Senior Center and Police usually still have room at lunch.
What Westpark does
Westpark shows which lots likely have room right now, how long you can stay, and how to get there. It starts from the town’s own parking counts.
Sources
- Town of Westport: Town reinstates timed parking enforcement
- Westport Journal: New time limits on downtown parking official as of Wednesday
- Westport Journal: Parking shifts: all-day spaces under pressure as new rules kick in
- 06880: Consultants: spread parking from downtown core; no deck now
- Westport Patch: Westport makes decision on downtown parking limit
- Town of Westport: Downtown parking time limit signs to be installed August 4
Stop circling.
Every downtown lot, right now. Free to use, always, with nothing to download.