Finding a spot near where you want to be is harder than it should be.

It's a density problem, not a supply problem

There's no shortage of parking in downtown Westport. The Imperial Avenue lot has 175 all-day spaces. Town Hall has 131. The Senior Center lot has 113. On most days, those lots have room. The problem is that most people don't head there first — and they shouldn't have to guess.

The most in-demand spots are the ones closest to retail: Parker Harding Plaza (211 timed spaces behind Main Street), Baldwin Lot (97 all-day and 60 timed spaces on Elm Street), and a handful of on-street spots on Main, Church Lane, and Jesup Road. These fill up quickly on busy days, and once they're gone, drivers who don't know the alternatives start circling.

The information gap is real. If you knew Imperial Avenue had 40 open spaces right now, you'd probably park there. But you don't know — because there's no way to know. That's what Westpark is for.

How the rules have evolved

• Pre-2020: On-street spaces carried 1–2 hour limits. Town-owned lots had mixed timed and all-day options.
• Spring 2020: The town suspended all parking time limits during the COVID pandemic to encourage downtown visits.
• May 1, 2024: Time limits were reinstated. Town-owned lots and on-street spaces moved to a 3-hour maximum (8am–6pm, 7 days a week), up from the pre-pandemic 1–2 hour limits. Fines: $25 for exceeding 3 hours, $50 for exceeding 6 hours. About 550 spaces were affected.
• Summer 2025: Following a BFJ Company parking study and public input, the Local Traffic Authority voted on July 9 to reduce on-street limits on Bay Street, Elm Street, Main Street, Jesup Road, and Church Lane from 3 hours to 2 hours. New signage went up August 4, 2025.
• Today: On-street parking in the core downtown: 2-hour limit. Town-owned lots: 3-hour timed spaces and all-day options. The all-day orange-striped spaces in Baldwin and elsewhere typically fill by 9am on weekdays.

This is an evolving situation. The town is actively studying further changes, including a broader downtown revitalization project (Reconnecting the Riverfront) with a target completion of 2027. We'll update this page as rules change.

The employee parking bind

For downtown businesses, the timed limits create a daily puzzle. Employees working 8-hour shifts can't use the 2-hour on-street spaces or the 3-hour lot spaces. The all-day lots — Imperial Avenue, Town Hall, Senior Center — exist for exactly this reason. But those orange-striped all-day spaces fill by 9am most weekday mornings.

A manager at a downtown clothing store described the situation to the Westport Journal: she has at least one employee every day who can't find an all-day space near the store and has to move their car every three hours. It's a friction that compounds quietly over months.

Westpark helps employees find available all-day spaces at the start of their shift — before they default to a timed spot and face the same problem at noon.

Source: Westport Journal, June 2024

What Westpark does

Westpark is a free web app — no download required — built for downtown Westport. Locals open it on any phone and report what they see at a lot: open, filling, or full. Those reports, combined with time of day, weather, the Westport community calendar, and school schedules, produce a real-time prediction for every lot.

Right now, Westpark covers all 20 downtown retail lots. Train station parking and beach parking are on the roadmap — we expect to add Saugatuck Station in 2026 and Compo Beach seasonal coverage in 2026 as well.

The model improves as more locals report. In the early months, predictions will be directionally useful but imperfect — we need thousands of reports to build a reliable baseline. The more the community contributes, the smarter it gets.