Downtown: This Is Our Embarcadero Moment

In 1989, the Loma Prieta earthquake rocked San Francisco. Twelve people were killed. Fires raged. And the Embarcadero Freeway was severely damaged.

Built in the 1950s to connect the Golden Gate and Bay Bridges — but never completed — the enormous double-deck highway instead cut the city off from its waterfront.

The Embarcadero Freeway. The Ferry Building is center left, with the clock.

For years, there had been talk of removing or redesigning the freeway. The earthquake provided a once-in-a-lifetime opportunity to do so.

Opposition was intense. But when the highway was demolished, a couple of things happened. More than 100 acres of land was redeveloped into a spectacular new public plaza and waterfront promenade. The area sprang to life.

The Embarcadero today. The Ferry Building is its centerpiece, but the entire area pulses with activity.

The 1898 Ferry Building became a vibrant gathering spot for local farmers, artisan producers, and independent food businesses. Commercial real estate boomed. Housing increased dramatically. The entire city benefited.

Today, Westport has our Embarcadero moment.

On March 3 — less than 2 weeks before our world changed forever — I posted a long story on “06880.”

Headlined “Main Street at an Inflection Point: An ‘06880’ Call to Action,” it noted that despite what we like to think, Main Street is no longer our “main street.” It’s just a short stretch of commercial buildings, many of them vacant.

But boy, I wrote, does it have potential. I continued:

The problem is, “potential” implies re-imagining the future. And re-designing the present.

We can’t simply tweak the Post Road. We need to (almost) blow it up, and start again.

The possibilities are endless.

Main Street could be a car-less, pedestrian-friendly piazza/ promenade lined with trees, tables and benches; upscale and family restaurants and cafes, including outside dining (with space heaters for winter); food carts and artists’ kiosks; independent businesses like a general store, bookstore and ice cream shop (joining the special Savvy + Grace-type places already there).

Look at the river. Look at Main Street. Imagine the possibilities. (Drone photo by John Videler/Videler Photography)

It could be filled with cultural and arts events; food festivals, and something at Christmas; music on weekends, plus waterfront access, with paddleboat and kayak rentals. In the winter, we could flood part of it for a skating rink.

And more: The Farmers’ Market could relocate there. We could add offices for non-profits, and co-working spaces. Apartments could be build on 2nd and 3rd floors.

Downtown, I said, was at an inflection point. Just as 70 yeas ago the area was re-imagined when landfill created Parker Harding Plaza, we needed a new downtown.

And change could not be incremental. It must be “big, bright and bold.”

The story drew 86 comments. This being Westport, they ranged all over the place: from why it couldn’t work, to lesser tweaks, to offers to help make it a reality ASAP.

What united us all was a common goal: to make downtown vibrant and alive, while looking ahead.

Had we looked behind, we would have seen the coronavirus galloping toward us. But now that it has, we have a once-in-a-lifetime opportunity to remake downtown, the right way.

Remember I said we should “(almost) blow it up, and start again”?

Now we really can.

I’m envisioning an even more dramatic reimagining than the one just 3 months — aka many light-years — ago.

Despite its horrors, the pandemic has taught us a few important lessons. Even when the danger passes, our lives will be vastly different from before. The way we work, eat, shop and spend our leisure time has changed, in ways we don’t yet fully understand. And although we have done certain things certain ways for longer than any of us have been alive, we learn very quickly how to do them in completely new ways.

Main Street, not long ago. (Photo/Sharon Fiarman)

Even during the shutdown, renovation continued on a few Main Street buildings. But we all know: Retail is altered forever. The big chains that forced out locally owned shops have swiftly contracted. Some are already bankrupt. More will follow. Betting that a new women’s clothing store, “lifestyle brand” or sunglasses shop will save Main Street is like believing that drinking bleach will kill a virus.

So to the vision I proposed on March 3 — a promenade filled with restaurants and cafes, food carts and artists’ kiosks; a general store, book store, and ice cream shop; cultural and arts events; the Farmers’ Market, offices, non-profits, apartments — I’d like to add a few more: a parking garage, with athletic fields on top. Fire pits. That elusive movie theater. Maybe even that long-discussed bridge over the river to the west bank.

And now I have an even more dramatic idea.

Let’s build it all the right way, at the right place: alongside the river.

It’s time to reclaim the river. San Antonio’s done it; so has Providence. This is our chance to actually, spiritually, emotionally — and physically — create an entirely new downtown.

Waterfire draws huge crowds to downtown Providence. It — and a reimagined waterfront — helped revitalize the city.

Let’s get rid of Parker Harding Plaza. Let’s tear down most of the buildings on Main Street. Let’s redesign everything from the Post Road to Avery Place, from scratch.

A proposal like this demands a lot from everyone. We’ll need the cooperation of property owners. That’s not easy in the best of times. But paradoxically, this might be the best time. What REIT in its right mind wants to hold on to a building whose tenant relies on a February 2020 retail model — with no other businesses to replace them in sight?

We’ll need the cooperation of town officials. Again, that’s not as far-fetched as it seems. Where once it took weeks to approve an awning or agree on sidewalk paving standards, the past few days have seen lightning-quick action on outdoor dining applications and new town regulations.

“We’re all in this together” can be a meaningless phrase. These days, local government, civic groups, merchants and restaurant owners have shown it can be a reality.

We’ll need the cooperation too of Westporters. Our downtown transformation won’t happen overnight. We’ll be building a house while also living in it. But if the past 3 months have shown us anything, it’s that our homes — our residences, and our home community — are vital to everything we do.

Look at that huge parking lot by the river. And the long line of boxy stores behind it. (Drone photo/Brandon Malin)

So that’s my plan. It’s a way to re-imagine, renovate and recharge Westport, for generations to come.

It’s a way to put hundreds of people — construction workers first, then employees — to work. It’s a way to draw countless others downtown, to be entertained, eat, enjoy themselves, and live.

Let’s not let this slip away. We can’t content ourselves dreaming that some day — hopefully soon — Americans will begin shopping in stores again, the same way they did before. And remember: On March 3, we weren’t exactly doing that either.

Magical thinking like that leads us right down the path of the guys who said, a couple of years ago, “Hey! Let’s build a mall in Norwalk, right next to Exit 16. What could possibly go wrong?!”

This is the start of the post-pandemic world. This is the time for truly bold, really creative, way-forward thinking.

This is our Embarcadero moment.

55 responses to “Downtown: This Is Our Embarcadero Moment

  1. John Brandt

    Aside from an endless list of “why nots,” you’ve cut to the chase and given us a fresh look at an historically flat-lined heart to our town. This could be the impetus to using the paddles to get it beating again. The challenge is to find the right team to diagnose and treat the patient. I remember coming to Main Street in 1948 and seeing Norman Rockwell spring to life. It’s time for Norman, and a community of forward thinkers who love Westport, to contribute to a better version of 1948. It’s time for Westport to put people first in designing our downtown’s future. I agree with you that we’ll all be the better for it.

  2. Roberta Tager

    ⭐️⭐️⭐️⭐️ Yesssss‼️😊

    Sent from my iPhone Bobbi


  3. Dorothy Robertshaw

    I am in how can I help 👍❤️🍹👌🏼👩🏼‍🎤🙆🏽‍♂️🙏🏼❤️

    Sent from my iPhone


  4. Stacie Curran

    Thanks for thinking big Dan – Where can we roll up our sleeves and assist? Loving the movie-theater and ballfields – Maybe ball-field space could second as a drive-in theater by night. “If you dream it, they will come”.

  5. Michael Calise

    Sounds good but unfortunately it needs $$$$$ from a business plan and pursuit that may have been failing long before it began. The Y leaving downtown may have been the final blow bur certainly the almost total disregard for a long needed river dredging and implementation plan instead of such useless feel good projects like the realignment of an already functioning Myrtle Avenue intersection and chasing a way finding signage program in the face of an abundance of way finding technology on ubiquitous devices. The sad fact is, as pointed out recently by town officials,
    the riverbed is filling to the point of no return due to federal restrictions. Keep up the heat Dan, you are asking for common sense to prevail which is a burdensome task.

  6. Without doubt or question. Let’s do it.

  7. YES! YES!YES! this is brilliant and so needed in Westport to revive the downtown!


  9. Babette Lienhard

    I think it’s a brilliant idea! Just imagining it gives me chills.

  10. Larry Weisman

    The Coalition for Westport has been saying something similar for some time now,as witness the « Downtown Westport » recommendations in the «
    « Positions » Section of our website, and the ideas generated by our public forum on reimagining downtown.
    We are gratified to see that these good ideas have begun to be taken seriously by others and we welcome Dan’s contribution to the discussion.

  11. Sooo-z Mastropietro

    Waterfire is a fantastic idea and I’ve been blabbing about a pedestrian footbridge for years. Our own Pontevecchio!

  12. Brett Adams

    Let’s do it!

  13. Wow. Just WOW!



    Regi Kendig 24 Goodhill Rd Weston,CT 06883 203-803-0236


  15. John Dodig

    Now, this is a real vision! Kudos for posting this. When you mentioned the renovation of the river front in Providence, R. I. you had me hooked. If it means taxes go up a bit, so be it. Our property values will soar with such a visionary change to our town center.

  16. Polly Newman

    LOVE your idea for Westport along the river. I visit Australia often and their pedestrian streets contain many items and small areas for kids to play and crawl on. That invites families and keeps them in the area because their kids are amused. The benches aren’t just regular benches but rather artsy colorful pieces. They also use a lot of AstroTurf. Giant games, like chess and checkers, are also popular. They hold a market every Saturday morning in the Spring and Summer.

    Let’s do it!!!! Thanks for all you do Dan!!

    Here are just a few photos of the Melbourne area:

    All the best, Polly

    Polly Newman Cell 561.301.5114

    Sent from my iPhone



  18. Sounds wonderful. Certainly getting a committee together of town officials,downtown merchants,interested citzens, City planners and financial folks would be a great start. It would be a visionary journey worth pursuing. Let us begin to begin.The Times They are a Changin

  19. Hilary Nordholm

    I love this vision Dan! Thinking of how under appreciated our waterfront is, I have often imagined something very similar! I went to RISD in Providence, and was there during their huge waterfront restoration project downtown. It was amazing to see. The ‘WaterFire’ bonfires are a sight to behold, and the food vendors and crowds it attracts to walk the waterfront or take a gondola ride are impressive. You’re right, this would take an enormous amount of collaboration from many moving parts, but it would be so worth it!!

  20. Myles J. Seideman

    Great idea. Creative. Will beautify
    and revitalize that section of Westport.
    Let’s do it.

  21. Julie Van Norden

    I absolutely love this idea. I can’t even imagine the logistics but it’s a lovely dream. The pushback from landlords is going to be huge as well as from the town government during a time of fiscal retrenching. But putting the dream out there is a wonderful first step!

  22. Bill Kirby

    Dan,We lived in SF before, during and after the Embarcadero came down. The transformation was incredible.Your analogy to Main st and the river is spot on. Well done.

    • Bill Boyd Staples 66

      This probably has been suggested…and will likely not pass environmental laws…but.. How about filling in the eastern edge of the river bank to great an acre park. (between the Parker Harding Plaza/parking and the river) maintaining parking while adding a “Park.” Other idea…build a dam up river of the Cohen Bridge creating consistent deeper water (this is quite complicated with runs…laws etc..etc..) Just some thoughts. But the environment comes first!

  23. LOVE!!

  24. Bill Webster

    Love your post today. I’m was born and raised in Hamilton, Ohio – part of the “Rust Belt” where most of the manufacturing industry had abandoned years ago. Here is a short video with their new direction for river front development – a bigger town, with bigger ideas , buy a radical redo as you suggest for downtown. Thought you might enjoy!

  25. Rozanne Gates

    Next step? Sounds like the energy and support is building. When I was Director of Development at Fairfield Theatre Company (FTC) there was this warehouse attached to the main building where the stage was. It was a huge space that was crying out to be transformed into a performance space. Several times I went to the Board of Directors with my vision and plan for that space and every time I was met with resistance. Comments like, “but the roof is not up to code,” “it will cost a lot of money,” “what would be the point of having two stages?” I continually told them that it wasn’t about money, it was about commitment. If the Board was committed, the money would come. All you ever need is leadership – someone to show the way. Then came the financial disaster in 2008 and FTC was hit hard. Most of us were let go from our jobs. Then a new director came in, a new Board was assembled and lo and behold, my vision for the warehouse came to fruition. Anyone who has seen a concert at the FTC Warehouse can not begin to imagine what it was like before it became what it is today. I know exactly what it looked like and it was horrible. Westport – you have a chance to have a big bold vision. All you need is the leadership. Who will that be?

  26. Jamie Klein

    Brilliant thinking!

  27. Christine Freeman

    Love the vision, however, I would keep some of the shops/entertainment/culture on the other side of Main Street – opposite the River side – as well with a number of open air/fields entrances from the River side to the Church Street side. Maybe there is a way to link the Library and its River park/views? Open up the entire S P A C E !

  28. Danielle Dobin, P&Z Chair

    Dan – this is spot on. It’s time consider meaningful changes to the landscape of downtown including the creation of a real riverfront and a multi-use sports field, even a pickleball court. Downtown can’t thrive if it’s just a spot people drive by on their way somewhere else. You and I were set to host an expansive forum at the library to discuss these ideas pre-covid. Let’s figure out a way to continue the community conversation now…maybe a big zoom meeting or a series of smaller ones to hear ideas and brainstorm as a community?

  29. This is a great vision, and these kinds of ideas have not been lying fallow with anyone associated with Downtown for some time. Both public and private investment to upgrade and improve Downtown has been significant over the past few years – from many new buildings and updates, underground cables, upgraded roads, sidewalks and parking lots (and yes, more to come on that front.) While we’ve lost some chains due mostly to circumstances that are a part of national strategy, we’ve also started to get the right kind of replacements – 2 new local restaurants and 3-4 small speciality chains that should open in the new few months. We are also benefiting from the “urban flight” with both new consumers who are temporarily or permanently locating here, and even some interest from urban merchants who want to do the same.

    Most immediately, there plans afoot to provide more social spaciousness and a safe welcoming environment for visitors. While these measures will be on a trial basis, with strong merchant and consumer support, they could evolve to becoming more permanent. To make all this a reality, we need more than talk – short term, we will need volunteers to help physically execute some of the work. Now and going forward what we really need is shopping support for our existing merchants – choose local FIRST. If we all do this, we will attract more offerings and greater, and continued public and private investment.

  30. John Richers

    I agree!! This is THE most opportune to start imagineering what Westport SHOULD be!! The existing Main Street’s retail model was doomed before the pandemic hit and now is the time to take bold steps to make Main Street and the riverfront a vibrant leisure and entertainment magnet!

  31. Phillip Perri

    Sorry to rain on the parade but also to suggest some sunshine as well. I’m guessing, as a public highway, the Embarcadero project included very little private ownership to deal with, as opposed to downtown Westport. Any private-owned land was probably pretty worthless at the time as well. So if we assume town cooperation from a planning perspective how to deal with private ownership? Enter the WDDG; Westport Downtown Development Group; a non-profit organization made up of quality, proven, locally connected, development professionals (Mr. Waldman?) who VOLUNTEER as board members (no politicians) to provide the expertise to reimagine, actually produce and MANAGE the kind of plan Dan suggests, as Mr. Waldman has already done. I also wouldn’t stop at downtown but include Post Road to Exit 18 as well as the adjacent school properties/Wakeman Farm with an eye towards recreational opportunities to drive visitors to downtown (sports tournaments, etc, kids, Playhouse, even dogs at Winslow). Something for every age and species. Also finally driving enough visitors to make economic sense of a movie theater. This could also benefit our school system with funding if set up correctly. The most important town contribution? Eminent Domain (condemnation for the public good). Steps:
    Create and authorize the WDDG
    Raise initial funds for overall phased design
    Complete a phased overall design
    Start negotiation on Phase 1: LLs can cooperate and be part of the much more lucrative downtown or they are paid market value for their property under E.D. If they participate, create a joint venture with each to maximize the income stream from each redeveloped property and the WDDG becomes a partner in the profit, thereby sustaining the viability of the downtown district management team of the WDDG…..also non-profit and necessary to maintain the new downtown amenities forever, at no cost to the town.
    Complete each phase to garner the most potential profit first.
    The project not only gets the downtown totally revitalized and reconnected to a new, overall “activity district” to feed it but also provides funding for continued management of the downtown facilities, school funding, funding to develop the properties that are taken by E.D. which the WDDG would then develop as funding allows and enjoy the total return. It also provides the shopping base that will finally support the retail viability of downtown (which is the problem now) and mitigates the potential impact of increased traffic.
    Underground parking, retail ground floor and multiple levels of residential should be part of every redeveloped property. By developing multiple properties under the WDDG, as a non profit, we can assure that a proper percentage of the apts would be affordable and available at an income level younger families could afford. That creates a “farm system” to feed Westport residential (and tax base) forever. Younger families grow into single family homes, older residents, who’d like to stay in Westport, down size to apts and lessen their tax bite, freeing up the housing stock for the younger buyers with rising incomes.
    There’s your practical and realistic road map. Vision is nice (and necessary) but realistic action and commitment is what’s needed.

    • John D McCarthy

      Eminent Domain….Based on the desires of unelected volunteers. Now, you might have lost some people with that.

  32. Daryl Styner-Presley

    So well put, and conceptualized! How do we assemble a team to take that vision, and all it’s many components, to talk together and have that vision come alive. Yes, it will take a lot of money, but part of that team may need to be a group who investigates federal & state grants, non-profit interest in investments, along with other development people looking for a visionary investment. But what this would offer long term could be priceless!

  33. BRAVO!!!!!

  34. Luisa Francoeur

    Dan, you are spot on. The time is now ! WDDG should begin working on this as Mr Perri comments above.

  35. Isabelle Breen

    Grand and so exciting!!

  36. Wyatt Jansen

    I’m not so sure private ownership is an impediment. I recently moved here from Greenwich, which is in the early stages of implementing a very ambitious plan to redevelop the area surrounding the train station (including the movie theater!) to encourage greater public access to and use of the space and discourage the use of prime real estate for parking. The town has done so in collaboration with (and with funding commitments from) private property owners including Ashforth, which owns Greenwich Plaza, as well as the MTA, which obviously owns the station and tracks. Identifying and working with major private property owners could be the solution, not the problem. Here’s some information on the Greenwich project, for those interested:

  37. Roseann Spengler

    WOW! Wouldn’t that be wonderful.
    Spot on, Dan.

  38. John Kelley

    One problem is that Westport is car dependent, so parking has to be easy to get into and out of–yet unless it is underground, a parking garage could be an eyesore and obstruction, yet would underground parking be considered as easy and safe? Bringing offices into the area would bring in more people.
    I’m not sure if this would work, but a hydrofoil boat to the railroad station might bring in people–perhaps even extend it to across Long Island Sound, La Guardia Airport or Manhattan. (A hydrofoil to La Guardia seems like a good idea, regardless.) And, as I mentioned in a comment to the previous post, as an intermediate step, close off Main St. one evening a week in season, put out tables and seats, and have a community dinner. Restaurants on Main Street can sell food as take out (as they are doing now), and perhaps some live music.

  39. Phillip Perri

    John: Thanks for your response however the WDDG recommendation for use of eminent domain would need to be vetted, approved and authorized by Planning and Zoning at a minimum. Its use cannot be approved by private individuals nor the WDDG and be considered in the “public interest”. Thanks for pointing that out.

    • John D. McCarthy

      I should have just written……Eminent domain, you might have lost some people with that.

  40. Katie P. Augustyn

    Love it, Dan!

  41. Bob Gifford

    Great fresh thoughts. Having a few architectural renditions to promote and entice visually would be great.

  42. Robert Harrington

    A bold vision and I know others are excited about the true potential of a new downtown. There will be so many obstacles and reasons why they can’t happen – and we all collectively need to work through them and find a way. An underground parking lot with recreational space on top is central to this and the key to getting this moving. I think a public virtual meeting is a great step forward. The costs will be large, but the true costs of not taking this bold action will be far greater over time. The cannot be a political football. Everyone needs to work together for the benefit of of mid to long term Westport.

  43. Valerie Smith-Malin

    In 2012-13 there was a Downtown 2020 committee, formed under former First Selectman Gordon Joseloff and chaired by Lou Gagliano.The goal of the committee was to work with DPIC recommendations and bring vibrancy and businesses to Downtown. The target felt way-off, the year 2020! The members had many of the same ideas and did a lot of research on layouts, legal entities and funding approaches that other towns have utilized, if residents so desired. A beneficial outcome was that the committee secured funding for the new brick sidewalks. Although work ended prior to the public input phase, I imagine the knowledge gained is preserved via archived minutes and documents.

  44. Rich Stein

    One hell of a concept… and vision… some great thoughts…. now we need action… if they could make a parking lot and create the levitt … they sure as hell can make downtown a vibrant park like place

  45. Amy Schneider


  46. John Kelley

    Let me amend my previous comment, after a days sleep. What downtown needs is foot traffic, and to get that, rather depend solely on drivers, let’s encourage the building of offices and apartments in the downtown area (high end, of course, this being Westport). For the offices, we would need frequent high speed transportation to the railroad station–hydrofoil boats, a monorail, a grade separated streetcar line or whatever. This would bring the foot traffic necessary for the reestablishment of restaurants and other retail.

  47. Andy Friedland

    Love this Dan, we’re facing of big changes in the way our world works, it’s time for more big ideas like this to meet the moment.

  48. I agree. And has a real estate executive have the means to put a plan in place to execute. Let me know the best way to get in touch. I have some ideas

  49. Phillip Perri

    It seems if it were up to “06880” readers the “plan” would get done. Alas it’s not nearly that easy. The example I suggested would be a herculean effort which would take a public-private partnership almost unheard of. That said I also believe we have the locally-connected, Westport-loving, realistic visionaries and “do-ers” needed to make this happen. The one large barrier is Town support and willingness to take action when the time comes. I would suggest the first step be a meeting of interested development professionals and Town planning representatives to take the temperature and appetite of everyone to actually take this on. I know most Town planning representatives read this blog so anyone interested and supportive? The most important aspect of the proposed WDDG is that it MUST be free of political influence and partisan politics on a daily basis. There would be oversight and controls above and outside the WDDG of course, however in my opinion, the only way the organization would work is to operate as a private development company would. Think of it as a non-profit quasi-public benefit corporation. There are plenty examples of such entities being formed to operate with all the positives of being outside the political arena but yet with oversight to ensure operating in the public good. I have personal knowledge of one in particular, The Facilities Development Corporation of the State of NY, founded by Gov. Cuomo (Mario not Andrew) as a prime example. So, Dan S. if this hasn’t scared you off, please email me at so we can compare ideas. Anyone else interested in an exploratory meeting please feel free to also drop me a note. Mr. Waldman, are you there? Every journey starts with one step.

  50. Wendy Cusick

    I suggest the “powers that be” figure out a way to dredge the river.
    You want to be a destination place for food and activities on the waterfront to attract boaters, kayakers and paddle boaders to come.
    You better get ‘cracking’ because it’s mud flats at low tide and a foot or 2 maybe? at high tide.
    At low tide it looks like a green lawn on the west bank just looking north of the Saugatuck River Rt 1 bridge. As the weather gets hotter, low tide might not be very pleasant.
    You’re not going to need a bridge from the west bank to the east back just walk across.
    At the moment, it’s looks only ankle to knee deep.
    Check out all the seagulls, ducks, sandpiper and egrets hanging out they’re STANDING or SITTING at low tide. If they want to eat the fish they wade out into the couple inches of water.

  51. As a former land use planner, love the concepts. as a former Weston/Westport resident (Staples Class of 65), always sad to see old favorites disappear: Klein’s, Oscar’s, the little jewelry store where my girlfriend worked, and of course The Ships, which we helped make into The Hangout. But they’re gone and a new downtown will make new memories for future Wreckers. Good luck.