"Most Westporters never even realized there was a bridge on Jesup Road at all," 06880 wrote on October 1. The blog described it as "really just a tiny bit of road a few yards from Imperial Avenue." The Westport Journal has reported it as roughly 15 feet from Imperial.
Since the September 13 storm, that stretch has been closed to both cars and pedestrians. Jesup Road is shut from Imperial Avenue to Bay Street. The span is tiny, but it carried a lot of traffic. Until the town replaces it, the only ways to drive into the Library side of downtown are two short one-way streets most people only ever used for parking.
What Fifteen Feet of Road Was Carrying
On a map, the Jesup Road bridge looks like nothing. In practice it was the back door between two halves of downtown. On one side are the Imperial Avenue lot and Post Road East. On the other are the Westport Library, Jesup Green, Levitt Pavilion, the Taylor lot and police headquarters. 06880's September 15 roundup listed exactly those destinations and called the bridge a way to skip the parallel stretch of the Post Road.
It mattered most for emergency crews. In the October 1 post, 06880 called it the quickest route for police and EMS, whose headquarters sit just up the hill, to reach almost anywhere in town east of the Saugatuck River. The town tested it. The Westport Journal reported that EMS response times showed no significant change overall. The First Selectman said calls on Imperial Avenue south of the bridge could take about 30 seconds to one minute longer, and calls south of Jesup Road but east of Imperial showed no difference.
For everyone else, the bridge is missed in smaller ways. RTM member Nancy Kail told the Board of Finance that the closure was hurting the Library and downtown businesses, and she called the traffic at the Imperial Avenue farmers' market "awful," according to the Westport Journal's October 8 report. One reader commenting on 06880 said she had used the bridge daily, both as a driving shortcut and as a walking route to the Library, and now walks around by way of Bay Street instead.
Why the Fix Is Measured in Seasons
On October 8, the Representative Town Meeting voted 26-0 to approve $172,500 for the initial design and permitting of a replacement, the Westport Journal reported. That money pays for paperwork and engineering. Construction will need separate funding.
Public Works Director Larry Roberts explained the timeline to the RTM. The new bridge has to be wider so Deadman Brook can flow under it more freely, and it needs "hardier abutments." The brook is also tidal, so permits take longer to review. According to the Westport Journal's reporting on the Board of Finance meeting, DEEP, the U.S. Army Corps of Engineers and possibly the state DOT may all have a role in permitting.
Money adds its own delay. Roberts said the town knows of a state grant that would cover half of the estimated $3-million-plus construction cost, but grants don't pay back costs after the fact. "We can't build the bridge first and then get paid back for it," he said. When an RTM member asked whether paying the full cost locally would speed things up, Roberts said design, engineering and permitting would take about the same time either way. He added:
"We are going to make it larger and that triggers additional permitting. Eighteen months is an expedited timeline."
Some work can move sooner. Roberts said the damaged bridge can come down before any grant arrives, because a collapse could block the brook. The Westport Journal put the removal estimate at about $40,000. As of October 12, no demolition date has been announced. Design proposals are due October 28, according to the town's September 30 notice.
A temporary bridge is still under discussion. Roberts priced a prefabricated span at about $300,000. He noted that the existing abutments would need repair and that the bottleneck in the brook would remain. In earlier RTM committee coverage, he also pointed to the nearby Imperial Avenue intersection and the limited room to install one. Roberts also said a permanent replacement built off-site is under consideration, much like the pre-cast concrete bridge on Cross Highway.
Two Short Streets Now Carry the Load
With the back door closed, that traffic has to come in from the Post Road side. That puts the pressure on Bay Street and Taylor Place, two streets you can walk end to end in less than a minute.
Bay Street runs from Post Road East past Design Within Reach and the Cake Box down to Jesup Road. Taylor Place is even shorter. It links the lower Library lot at the foot of Jesup Green to the Post Road, between Tonic & Green and Tiffany. Several residents independently suggested making both streets two-way, 06880 reported. The town is now weighing the same idea, though the two streets face very different paperwork.
| Bay Street | Taylor Place | |
|---|---|---|
| Current direction | One-way away from Post Road East | One-way toward the Post Road |
| What two-way would take | Signs and pavement stripes | State DOT involvement, because of the traffic signal and pedestrian crossing at the Post Road |
| What would be lost | On-street parking on both sides | A few 15-minute spaces and a delivery zone |
| Status as of Oct. 12 | Roberts has said the town plans to make it two-way | Roberts called it more problematic |
The town's goal, as the Westport Journal described it, is to take pressure off the intersection of Post Road East, Imperial Avenue and Myrtle Avenue. Roberts told the RTM he would bring both plans to the Board of Selectmen on Wednesday. However, the revised official agenda for the October 14 meeting at 9 a.m. lists only one Local Traffic Authority item, Riverside Avenue striping. Bay Street and Taylor Place are not on it. Until that changes, Bay Street is still one-way with parking on both sides, and it is still the walking route that 06880 commenter described taking to the Library.
This Fall's Calendar, Sorted by Side of the Brook
Most of downtown's fall events are on the Library side, and the farmers' market is on the Imperial side. With the bridge closed, the short hop between them now goes around by way of the Post Road.
| Date | Event | Where | Side of the closure |
|---|---|---|---|
| Thursdays through Nov. 5, 10 a.m. to 2 p.m. | Westport Farmers' Market, final outdoor weeks | 50 Imperial Ave. | Imperial |
| Oct. 15 | Y's Men Presents: Sports Stories with Chris "Mad Dog" Russo, free tickets | Westport Library | Library |
| Oct. 16 | Read on the Green | Jesup Green | Library |
| Oct. 17 | Murray Hill in conversation with Jeff Hiller, $35 | Westport Library | Library |
| Oct. 22, 7 p.m. | Aspetuck Land Trust's free Haskins Lecture with Joan Maloof | Westport Library | Library |
| Oct. 28, rain date Oct. 29 | Children's Halloween Parade, trick-or-treating from 3:30 p.m. | Main Street to Avery Place and Myrtle Avenue | Downtown |
| Nov. 10, 7 to 8:30 p.m. | Book talk with Princeton President Christopher L. Eisgruber, free | Trefz Forum, Westport Library | Library |
| Nov. 12, 7 to 9 p.m. | Westport Prize for Literature ceremony with Patmeena Sabit, free | Trefz Forum, Westport Library | Library |
You can check times on the Westport Library calendar, the farmers' market site and the town's special events page. Our research didn't turn up a Library notice about parking or access during the closure. The Levitt Pavilion's October calendar was empty when we checked. We didn't find an announcement of a 2026–27 winter market location. The Gilbertie's arrangement the Westport Journal reported last year covered the 2025–26 season only.
The newest reason to stop on the Post Road side is hi'Amba, Bill Taibe's Eastern Mediterranean restaurant and market in the former Basso space. Its address is 33 Jesup Road, also listed as 76 Post Road East. 06880 reported that the soft opening on October 9 was packed all day, with a ground-floor bakery, dips, shawarma, skewers, and seating inside and out. The restaurant wasn't serving dinner yet. After that weekend, it planned to close for a couple of days to get ready for its full opening. As of October 12, no full-opening date or dinner hours had been announced.
Design proposals are due October 28. The Bay Street change and a date for removing the damaged bridge are both still to come. If you live or own near downtown and want to know how a long detour like this could affect what your home is worth, Lovisa Wisdom can walk you through it neighbor to neighbor. Start with your Instant Home Valuation, and she'll follow up with what she's seeing on these streets.
