At the bottom of Jesup Road, a few yards before it meets Imperial Avenue, a line of concrete Jersey barriers now blocks a piece of road most drivers never knew was a bridge. The 12-foot span crosses Dead Man's Brook. It sits on stacked native granite, dirt and fill, and Westport Journal accounts date it to either 1950 or 1952. After roughly 7 inches of rain on September 13, it became too dangerous to use. The Town says the bridge has been closed to both vehicles and pedestrians ever since.
What the closure really does is separate two halves of downtown that used to work as one. The Westport Library, Jesup Green, Levitt Pavilion and police headquarters sit on one side of the brook. The 50 Imperial Avenue lot and the Thursday Farmers' Market sit on the other. Until a new bridge opens, the only link between them is the Post Road, which the bridge existed to bypass.
Twelve Feet That Held Downtown Together
The span connected Imperial Avenue to the Library, police headquarters, Jesup Green, Levitt Pavilion and the Taylor parking lot. In a post titled "Roads Less Traveled," Dan Woog of 06880 described it as "really just a tiny bit of road a few yards from Imperial Avenue." He added that most Westporters "never even realized there was a bridge on Jesup Road at all."
It mattered more than its size suggested. Starting September 14, the Westport Journal reported that Jesup Road was closed from Imperial Avenue to Bay Street. That turned a short connector into a dead end on both ends. People coming from Imperial Avenue can no longer roll straight up to the Library's lower lot. People leaving Jesup Green can no longer drop down to Imperial without going through downtown first.
Public Works Director Larry Roberts told the Westport Journal the bridge was too damaged to repair. He estimated a replacement would take 12 to 18 months to open. "That is just an estimate right now," he said. "We're expediting the process, but we still have to go through the permitting process." Counted from a September closure, his range runs from fall 2027 into early 2028. The Town has not committed to that schedule. It says it will publish an anticipated construction schedule as the project moves forward.
The Post Road Is Back in Every Trip
The Town has not published a signed detour, and its September 30 notice lists no adopted traffic, signal or parking changes. It says only that it is "monitoring traffic patterns during the closure and evaluating potential adjustments." In practice, the Library side of downtown is now reached from the Post Road through two short streets that were never meant to carry this load:
- Bay Street, the short one-way road running from Post Road East past Design Within Reach and the Cake Box to Jesup Road. Cars currently park along both sides of it.
- Taylor Place, an even shorter road that runs from the Post Road, between Tonic & Green and Tiffany, to the lower Library parking lot at the foot of Jesup Green.
Residents have already proposed fixes. One would make Bay Street two-way and remove its parking. Another would make Taylor Place two-way, or split it into a left-or-straight lane and a right-turn lane, which would remove a few 15-minute spaces and a delivery zone. A third would take down the Imperial Avenue stop signs at Jesup Road, since there is nothing left to stop for. All three are reader suggestions collected by 06880. None has been adopted by the Town. For now, both streets work the way they did before the storm, with much more traffic.
Walkers face the same gap. The closure covers pedestrians, and the Town has not named a walking alternative. Going from a parked car on Imperial Avenue to a Library event now means going around rather than straight across.
The question many people asked first was emergency response, because Westport EMS and Westport Volunteer EMS dispatch from the police property on Jesup Road and together answer about 2,400 calls a year. EMS Chief Patrick Riddle ran test routes under emergency conditions. First Selectman Kevin Christie said the alternate route adds roughly 30 seconds to one minute for calls on Imperial Avenue south of the bridge. Testing found "no discernible difference" for calls south of Jesup Road and east of Imperial.
Which Side of the Brook Your Fall Plans Are On
Once the bridge is out of the picture, the fall calendar sorts by location. The things worth checking are which side of Dead Man's Brook an event is on and which street gets you there.
| Event | Date | Where it sits |
|---|---|---|
| Westport Farmers' Market | Thursdays, 10 a.m. to 2 p.m., through Nov. 5 | Imperial Avenue side, 50 Imperial Ave. |
| Amor Towles, Malloy Fund for the Arts | Thursday, Oct. 8, 7 to 8:30 p.m. | Library side; tickets no longer available |
| Walk Bike Westport "Bridge to Bridge" ride | Sunday, Oct. 18, 3:30 p.m. | Three miles to Saugatuck and back |
| Ken Ludwig's "Pride and Prejudice, Part 2: Napoleon at Pemberley" | Oct. 20 to Nov. 7 | Westport Country Playhouse |
| Halloween Window Painting Contest | Saturday, Oct. 24, 9 a.m. to 4 p.m. | Windows of participating merchants |
| Westport Book Sale, fall sale | Nov. 6 to Nov. 9 | Inside the Westport Library |
The Westport Farmers' Market lists its season as May 7 through November 5. That leaves five Thursdays as of today: October 8, 15, 22 and 29, plus November 5. Its website gives no access instructions related to the bridge. Anyone who used to pair a market run with a Library stop now has two parking decisions to make, not one.
Two of the dates fall back to back. The market closes for the season on Thursday, November 5, and the next morning the Westport Book Sale moves into the Library for four days. Organizers say detailed hours and specials will be posted closer to the sale. The Amor Towles conversation on October 8 is on a market Thursday, but it starts at 7 p.m., well after the market's 2 p.m. close.
The Walk Bike Westport ride on October 18 is for ages 8 and up, and helmets are required. Tickets for the Playhouse world premiere are listed from $50.
One river crossing is getting more useful this fall. A wooden dock now extends from the patio at Arezzo into the Saugatuck River, just south of the Ruth Steinkraus Cohen Bridge. In its October 5 roundup, 06880 called it Westport's first public dock and said it was "almost ready to open."
Why a Twelve-Foot Bridge Takes a Year
A replacement this small taking this long comes down to what the new one has to be. The Town's request for proposals covers surveys, hydraulic analysis, environmental review, design, permitting and bid support. Roberts said the replacement "needs to be designed for the larger storm events and hydraulic conditions we are experiencing today." The Town is working with the Connecticut Department of Energy and Environmental Protection on permitting, including possible emergency or expedited pathways. The goal is for permit requirements to shape the engineering from the start, not after it is done.
The site itself is part of the constraint. A temporary bridge is still being considered, but Roberts said cost estimates are needed before anyone decides. He also noted that Imperial Avenue runs only about 15 feet away, which limits where a temporary span could go. The Town says it is weighing whether an interim crossing could restore the connection safely and whether the cost would be "financially prudent." Roberts has also said the damaged bridge may be removed "in the near future" so no one tries to cross it. No date has been set.
On funding, Roberts said he hopes state and federal grants will cover construction, though the Town may have to pay for design.
The Dates That Decide How Long the Gap Lasts
The next three weeks set the pace:
- Wednesday, Oct. 7, 7:30 p.m. The Board of Finance considers a $172,500 appropriation for design, permitting and environmental investigation. The RTM's Finance, Public Works and Transit committees already recommended it 19 to 0, subject to the Board's approval.
- Thursday, Oct. 8, 7:30 p.m. A special RTM meeting takes up the same appropriation, according to Patch.
- Wednesday, Oct. 28. Engineering and design proposals are due, and the Town plans to pick a design team as soon as procurement allows.
Neither vote had taken place when this was published. A temporary-crossing decision and a demolition date are the other two announcements that would change how downtown works before a permanent bridge opens. Until any of those happen, getting from the Library side to Imperial Avenue means using the Post Road and either Bay Street or Taylor Place.
I'm a CPA, so I tend to read a public works timeline the way I'd read any project budget. I look at what has been funded, what has been approved, and which dates are still only estimates. If you're thinking about how a 12-to-18-month downtown project fits your own plans in Westport, Jillian Klaff can walk you through it. Request a personalized market consultation.
