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Autumn sunlight falls across a cedar-shingle home with white double-hung windows, a bluestone approach and oakleaf hydrangeas beside a broad lawn.

Downtown Westport's Shortcut Is Gone. Two Side Streets May Fill In.

October 15, 2026

The small 1952 bridge that carries Jesup Road over Deadman Brook, a few yards from Imperial Avenue, is closed. DPW Director Larry Roberts estimates a replacement likely won't open for 18 months. The town is moving fast. The delay comes from the work that has to happen before construction can start: permits from two agencies, a state grant that won't pay back money already spent, and a new design that has to be wider than the old one. Until then, downtown traffic will depend on what the town does with Bay Street and Taylor Place, two short one-way streets.

A bridge most people never noticed

06880 pointed out that most Westporters never realized there was a bridge on Jesup Road. It's "really just a tiny bit of road," at the foot of the street where Jesup meets Imperial Avenue. That changed on September 13. Roberts told the Westport Journal that about seven inches of rain fell in three hours. The water went over the bridge and tore away the rocks and earth holding it up, and he said the span was too damaged to repair.

The town's September 30 notice says the crossing is closed to cars and pedestrians. The week of October 5, a chain-link fence went up in front of the damaged bridge to keep people from walking across it. "That's how dangerous it is," Roberts told the Board of Finance. None of the town notices or local reports name an official detour.

What that little span was doing

People who drive downtown know the route. It took you to the Westport Library and the Levitt Pavilion without using the Post Road. 06880 pointed to a bigger job. Police and EMS are headquartered just up the hill on Jesup Road, and the bridge was their quickest way to almost anywhere in town east of the Saugatuck River.

Since the closure, traffic has backed up at the intersection of Post Road East, Imperial Avenue and Myrtle Avenue, according to the Westport Journal's report from the October 6 Board of Finance meeting. At that meeting, RTM District 9 member Nancy Kail said the closure was hurting the Westport Library and downtown businesses. She asked finance board members to visit the Westport Farmers' Market on Imperial Avenue on a Thursday, because traffic there was awful with the bridge closed.

"This is an important bridge. It's a very practical bridge." — Nancy Kail, RTM District 9, as reported by the Westport Journal

Liz Heyer, a Board of Finance member, asked whether traffic improvements could make a new bridge unnecessary. Roberts said the bridge does real work, both for emergency crews leaving the Police Department and for everyday traffic downtown. So the bridge is coming back. The open question is how long it takes and what downtown looks like until then.

Why a fast-tracked bridge still takes 18 months

The money has been approved. The Board of Finance voted 6-0 on October 6 for $172,500 to cover initial design and permitting, and the Representative Town Meeting gave final approval 26-0 on October 8. Roberts still told the RTM that a new bridge likely won't open for 18 months, mostly because of permits.

Here's what has to happen first, based on Roberts's statements to the two boards:

  1. Design proposals come in. The town has asked for proposals to design and engineer the new bridge. The Westport Journal reported they're due October 24. The town's own notice lists October 28.
  2. The design gets bigger. The new bridge has to be wider so Deadman Brook can flow under it more easily, and it needs "hardier abutments."
  3. Permits are reviewed. Deadman Brook is a tidal waterway, so the project needs permits from the state Department of Energy and Environmental Protection, the U.S. Army Corps of Engineers and possibly the state DOT.
  4. Grant money arrives. Roberts said the town knows of a state grant that would cover 50 percent of construction, which he estimates at more than $3 million. That grant has to come through before work starts.

Step four is the one that sets the pace. "We can't build the bridge first and then get paid back for it," Roberts told the RTM, according to the Westport Journal. "When all is said and done, it's important we get at least $1.5 million." Kail asked whether Westport could pay the whole cost itself and skip the wait. Roberts said design, engineering and permitting would take about the same amount of time either way. "Eighteen months is an expedited timeline," he said.

There is one way to save time. RTM District 7 member Larry Kleinman asked whether the new bridge could be built somewhere else and trucked in. Roberts said that idea is under consideration, and noted that the new bridge on Cross Highway was built from pre-cast concrete pieces and that the same approach "could very well be done here."

Why a temporary bridge is a hard sell

A temporary bridge would seem like the obvious fix. Roberts told the Board of Finance it hasn't been ruled out, but it has problems. A prefabricated span would cost about $300,000. The abutments under the damaged bridge would need repairs first. Water would still have too little room to flow underneath. A temporary bridge would also have to go up and over the damaged one, and there are only 15 to 20 feet between the Jesup Road bridge and Imperial Avenue.

Removing the damaged bridge is simpler. Roberts estimated that work at $40,000. It doesn't have to wait for grants, and the town may do it soon, because a collapse could block the brook underneath. The town's Public Works projects page lists the unsafe bridge for removal, but as of this writing no report says it has been taken down.

Bay Street and Taylor Place are where the daily changes happen

With no temporary bridge, two short streets would handle most of the change. Several Westporters suggested making both of them two-way in a 06880 post on October 1. DPW now has a version of that plan.

Bay Street Taylor Place
Where it runs From Post Road East to Jesup Road, past Design Within Reach and the Cake Box From the lower Library lot at the foot of Jesup Green to the Post Road, between Tonic & Green and Tiffany
Current direction One-way heading south off Post Road East One-way toward the Post Road
What a two-way change takes New signs and road striping, with no traffic light and no state DOT involvement State DOT approval, because there's a traffic light and a pedestrian crossing at the Post Road
What would be lost On-street parking along both sides A few 15-minute spaces and a delivery zone
Status as of Oct. 12 DPW told the Board of Finance the town plans to do it DOT is willing to change the light timing but not the pedestrian crossing

Bay Street is the easy one. Roberts said it's wide enough for two lanes, and the parking spaces that would disappear could be replaced by parking on nearby Jesup Road. He also said two-way traffic would let officers who aren't on patrol, and EMS crews based at the Police Department, reach calls in the southeast part of town faster. That brings back part of what the bridge used to do. Taylor Place is harder because the state controls the crosswalk.

Roberts told the RTM he would present both proposals to the Board of Selectmen this Wednesday, October 14, though the Westport Journal noted that the meeting agenda would need to be revised. Neither change has been adopted yet. The town's September 30 notice also says it's still looking at temporary access options and watching traffic for possible adjustments.

The next few weeks on Imperial Avenue

The Westport Farmers' Market lists Thursdays from 10 a.m. to 2 p.m. at 50 Imperial Avenue through November 5. That leaves four market days: October 15, 22 and 29, and November 5. October 22 is the busiest of them. That evening at 7 p.m., Aspetuck Land Trust is hosting its Haskins Lecture with author Joan Maloof at the Westport Library. It's free, with registration required, according to 06880. RTM member Peter Gold has suggested parking in the Imperial Avenue lot and walking to the Library. That's his idea, not official town guidance. The fence across the bridge means the walk from that lot has to go around the brook, not over it.

RTM District 9 member Jennifer Johnson called the design funding a "no brainer." She also said the town needs to deal with culverts before they turn into emergencies. Until the replacement opens, getting around downtown Westport will depend on what the selectmen decide about Bay Street and Taylor Place. If you know downtown from the summer Thursdays described in our late-August Westport guide, that route is changing this fall.

If you own near Jesup Green, Imperial Avenue or the Post Road and want to know how this closure could matter for your home over the next year and a half, Jennifer Lockwood Homes is following each vote. Request a complimentary market consultation, and we'll go over where things stand for your street.

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