Over its long history, Westport has seen thousands of restaurants come and go.
Everyone has favorites. Here are a few. Click “Comments” to add your own.
Allen’s Clam House was a great place for celebrations and dates. It was demolished more than a decade ago. The site is now the Sherwood Mill Pond Preserve.
(Photo courtesy of Dave Stalling)
The Big Top was a beloved hamburger place that attracted everyone: doctors, lawyers, businessmen, high school students, stoners and (very famously) Paul Newman. Today it’s McDonald’s. If that doesn’t say something…
Here it’s the Ocean House. For many years though it was Chubby Lane’s — the first $1 hamburger restaurant in town. The meat came from Charpentier’s butcher across the street, and it was fantastic. Today, this is the site of Willows Pediatrics.
Pearl’s was a longtime Riverside Avenue favorite. It’s easily recognized now, as Da Pietro’s.
Who can forget the Arrow? For years, the Nisticos’ restaurant defined Saugatuck. These days, it’s Mystic Market.
West Lake on Main Street was Westport’s first Chinese restaurant. It was considered to be quite exotic.
(Photo/Fred Cantor)
Originally a stagecoach stop in the 1700s, the Three Bears closed after many years. It’s been remodeled as Chabad of Westport.
The Three Bears, in its heyday. (Postcard/Cardcow.com)
The Clam Box drew diners for its seafood. The location — on the Post Road by the Sherwood Island Connector — did not hurt. It was later Bertucci’s; now the spot is shared by Shearwater Coffee, and soon-to-open Ignazio Pizza.
It is a shame they have all been substituted. As a long time resident of Westport, they are sorely missed, especially Allen’s since it is now merely a parking lot and neglected, overgrown area.
West Lake was on Main Street. In Parker-Harding.
Arrow , Allen’s and Clam Box all have so many great memories. I went to college with Wayne Ucillini
MARIOS !
ad DeRosas
I loved the salads at the Arrow! I also remember the Crest Drive-In which was very popular. I loved the fried clams from the Clam Box. Pearl’s was owned by Paula Pastorelli. She was in the Staples class of 1965. She was so entrepreneurial. I think she had developed and marketed a salad dressing recipe. I’d love to hear from her. I’ve basically lost contact with everyone in Westport.
Nothing better than a Ring Beef at the Big Top, Fish N’Chips at the Clam Box ….still miss them and the others. You forgot the Mansion Clam House…
Ok, so I didn’t grow up here, but we moved here in 1984. I miss Onion Alley. We enjoyed the food and the staff and probably ate there a few times a month.
Rocco’s was a favorite spot for us. My husband always ordered the Veal Francese. I usually did, too, but the occasional times I tried something else, while it was always good, I’d be jealous watching him eat his veal. We’d take our children, too, and when they finished eating we’d let them go to Arnie’s. We usually had a pre-Christmas dinner at Three Bears. And no place has as beautiful a site as the Old Mill in Weston. I miss most of the others mentioned but we certainly still have lots of places for good food all around town.
Oops! Of course I mean Cobb’s Mill Inn in Weston. How could I forget the name?
My favorite restaurant and what I miss still is Soup’son on Main Street!
These memories are terrific!
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Don’t forget Ships.
The Crest was a huge part of my coming of age – best chili dogs on the planet. The Three Bears and Cobb’s Mill were certainly favorites, as were the Normandie and the Mansion Clam house.
Although it wasn’t exactly a restaurant, the Ice Cream Parlor will always be near and dear to my heart.
Is the Sherwood Diner still in business?
Sherwood Diner is definitely still in business!
Thanks, Dan. The Sherwood Diner was our “go-to” place during our final years in Westport. We moved to North Carolina in 2013.
All our special events were celebrated at Allen’s Clam House, watching the swans from the windows
Full speed down Memory Lane! This was fun…, and tasty. The Arrow; how many lunches and dinners did I en-joy here, before and with family. The Big Top, the gathering place onceuponatime, once I had my license [and before trips to Vista and Port Chester]. Spent three Summers working at The Clam Box, in the dining room and kitchen. Good times, big Fun.
What about Porky Manero’s, across from the bridge, people? Gorgonzola salad dressing!!!
Thanks, Dan!
Best memory of Allen’s Clam House: the screen door in the reception area marked: “Keep Out – Employees Only.” It was nailed shut, but had you been able to walk through it, you’d instantly drop about 10 feet and land in the mud flats below. (At some point in history there were probably some steps there.) 2nd best memory: lobster dinner was $5.95 in late 60’s bucks, CPI calculator says that’s over $40 today. So lobster was a luxury, even back then.
I got food poisoning at Rocco’s, the ‘chef’ at Big Top wore a stained “wife beater” with a perennial cigarette in his mouth as he cooked, and as a dishwasher at Allen’s, along with my best friend, was brutalized by a staff member I should sue to this day. Sure I get the romanticizing of these places, often deserved, but there is a practical reason plus why they are not here anymore.
All this was the case from the time that Orwell wrote “Down and Out in Paris in London” to today, With the possible exception of food poisoning that gets traced to the source, the antics of behind-the-scenes staff have little to do with whether a restaurant succeeds or fails.
I never knew what food poisoning was until I ate a Carroll’s hamburger at the Wspt Nwlk line.
Ships ( seafood chowder) Ship’s Corner Chinese takeout, Onion Alley ( Turkey Salad with wild rice), Soup’s On, Connolly’s ( Teriyaki Chicken), Ed’s Diner ( that huge cheeseburger plate with french fries after Player’s Tavern last call), Oscar’s Roast Beef sandwiches and the big pickles, Art’s Deli and their Italian subs…
The 99cent ribs at Big Top with fries were way better than their burgers Though a more of a hangout how can one forget Bill’s SmokeshopAh the Westnor dinner and later Rudy’s in Parker Harding and the cheapest food around at the counter in the back of Ben Franklin’s five and dime Those were the fun days growing up here
I lived in Westport in 1967 and most of 1968, I was an au pair from Denmark. I remember many of those restaurants mentioned. Allan’s Clam Box, and the Clam Box, I have to check my notes from those years, but I’m pretty sure I have been to both. It seemed prices were reasonable enough that a date (usually a college student) could afford to take a date there for a drink and a bite to eat, no lobster dinner though. Big Top was a favorite for au pairs on our days off. I remember 3 Bears, don’t think I ever went there, but pretty sure a date took me to dinner at Cobbs Mills Inn for dinner, not a college student. Someone mentioned the Ice Cream Parlor, often went there after a movie, the Ice Cream Parlor was to me so very unique and American, and I loved the maple walnut sunday, we had nothing like that in Denmark, although our ice cream is quite good, very creamy, but back then we only have a few flavors, vanilla, chocolate, strawberry and nougat.
The Ships was our favorite hang out, lot’s of memories.
I seem to remember that either Allan’s Clam Box or the Clam Box was a favorite hang out of Paul Newman, unfortunately I never saw him there, or anywhere else for that matter, too bad. He was always a favorite of mine, both as an actor and classy human being, would have loved to run into him.
Le Chambord was our “go-to” spot for any occasion. The Grand Marnier souffle was a must but you had to order it when you ordered dinner.
You beat me with your post on La Chambord and I second it. Yes, the Grand Marnier Soufflé was the best and made even more special because you did have to order it when you ordered your meal. My husband and I spent many special occasions there. Thanks, Dan, for so many wonderful restaurant memories in this article – miss Allen’s, too. My dad was very close with Bert Ucillini back in the days and we ate many meals there.
Thanks for the stroll down memory lane. I also loved Chez Pierre, now Tavern on Main
Pepper Mill
Artist Pub then Connelly’s Restaurant
Cafe de la Plage, a fine place for a romantic high school prom date.
Maneros garlic bread and gorgonzola salad. Never duplicated!
Ha! The Ship’s…, where I drank as a 17, 18-year-old after work [Bridgeport Hydraulic], summers and evenings. Safer than driving to Vista or Port Chester. Always, there was a Westport cop working the traffic lights at the Post Road/Main Street intersection during early rush hour.
Shhh, so he didn’t turn around to see our young asses ducking into The Ship’s bar. Oh! what fun growing up in Westport.
Not sure anyone is missing the Ship’s nowadays, but onceuponatime….
I miss The Ship’s LANTERN. Those were the days.
Ships had a dish called the MOM it was a heart attack waiting to happen. Big Top burgers until the biggest grease fire took it down. Clam box had the best fried clams. Soups on amazing French onion miss it still.
I remember them all. Great memories.
DeRosa’s. Porky Manero’s. Ponderosa, Tin Whistle, Friendly’s
Moved to Westport in 1964. My family and i ate at all of them over the years.
Good memories. I can remember when Main St was a two way street. Used to buy gas at the Mobil station which is now Vineyard Vines.
One I remember that has not been mentioned was The Chanticleer on Elm Street.
I may not have spelled that correctly. By 1966 it was located on the Post Road as the dining room for the Motel that was located there. We held our wedding rehearsal dinner at the restaurant and the out of town guests stayed at the motel. And wasn’t there a Spinning Wheel restaurant?
Tacos or what? deserves a mention.
I can’t believe that no one has mentioned La Bibliotec, one of the best restaurants ever.
Killing me I can’t remember the name, but there was a place on the Post Road, where Crate & Barrel is now. Owned by the same couple that ran the hotel restaurant, The Emporium, in what was then the New Englander, now Westport Inn.
Mel and, uh, Judy? Axelrod. I worked at the Emporium for a while.
I don’t see it in this nice list “someone” made a while ago 😉
https://06880danwoog.com/2009/08/22/you-must-remember-these/
Steak and Brew was technically in Southport, wasn’t it?
(Worked there, too a while in H.S.)
John, Beansprouts? I remember eating there in 1987.
I remember driving to Vista, it was right across the state line to NY, and we would also go to Port Chester, back when I lived in Westport, the bars in New York state had different closing laws than CT, so we went there, when we couldn’t get a drink in CT. I think the location of Vista was kind of comical, as far as I remember it was just over the state line. Thinking back on all those places and the memories connected with them, make me realize I was very lucky to be young when I was, and lucky to be living in Westport at that time.
Chez Pierre and The Cafe De La Plage were favorites of my family.
The Ice Cream Parlor and The Big Top were my teenage hangouts!
I have an ash tray from Cafe Barna. I’m not even sure millennials know what an ash tray is.
Club 300 in Westport Lanes. That one hasn’t been mentioned yet nor has the Stage Door Restaurant been mentioned.
Hey Dan, wish you would give some indication of the dates of operation or at least about when the pics might have been taken.
I would have if I knew!
West Lake photo is from 1976.
We’ve got that post card for the Three Bears. My grandparents had their 50th wedding anniversary there, in 1991. I was a kid, but I remember the staff being wonderful and the food was always good. It’s sad that the other restaurants I would classify as similar – the Red Barn and Cobbs’s Mill in Weston both closed. Redding Roadhouse has been remodeled and is now very different. However, the Smithy in Monroe still has that down home, country/ Early American feeling. It’s just harder to find that type of restaurant these days.
We arrived in Westport in late 1960 and I was 3. I remember it so well. We moved at first to the same hood as the Big Top family. All of our families played kick ball and wiffle ball together, went to the beach together, chased the Good Humor man on hot summer nights together. It was a great time to live in Westport…the 1960s.
The memories and flavors of these old Westport restaurants can’t be duplicated. I remember the Chubby Lane burgers…they were amazing. And Big Top…never had those tastes again!
I’d like to give shout outs for the outliers we loved too. Carrolls on the border of Norwalk ..never had fries like that again, and Red Coach Inn..I remember their clam chowder and some sort of hamburger steak. Oh also Old McDonalds Farm. Loved their penny candy in their general store!
I have fond recollections of many of the places people are bringing up here, but I have a particular soft spot for Rocco’s, mentioned above by Ms. Barnhart.
My wife and I went there often when we were courting many years ago and Rocco began taking a fatherly interest in us, always greeting us warmly and making a genial show of getting us to our table. When we finally tied the knot at Christ and Holy Trinity Church here in town, we asked him to host our wedding reception afterwards at his restaurant, and it did so in his most gracious fashion. It was a completely modest affair by today’s standards, but that was the way we wanted it, and it remains one of the best memories of my life.
I can’t picture where Rocco’s was. I’m drawing a blank.
Post Road east, a few yards west of where your parents’ bowling alley was! Opposite the old Rippe’s Farm.
Want a postcard from there?
https://www.ebay.com/itm/Roccos-Specialita-Cucina-Italiana-Restaurant-Westport-Connecticut-CT-Postcard-/282626761808
Guy actually has a lot of old Westport cards for sale
John, much thanks for the picture. So many years have passed that I’d actually forgotten what the inside of the place looked like.
West Lake became Barney’s for a while, I can’t believe that no one has mentioned Muriels Diner!!…..That and the building on the corner burned downed Thanksgiving 1974, under suspicious circumstances. It became Krafts…….
I worked on Taylor Place. Ate at Muriel’s all the time. She was a character. I was working late one evening and out the window of my shop I saw the spark that started the ‘Klaff’s fire.’ Watched all night as our best and brightest brought it to its knees.
Klaffs….hate auto spell.
Also, the WestNor Diner on Post Rd West , across from the Artists Pub!
Westnor became a great jazz spoyt in, I think, the ’70s. I still have a swizzle stick from there!
Oops. Spot. Jazz spot.
We were married 62 years ago and had our wedding reception at the Townly restaurant on Main St. — near Klein’s stationery store.
I moved to Westport in 1983, so my memories don’t go as far back as many of you. But I remember — Ships, Soup’s On, Atticus Book Store, Remarkable, Laura Ashley, Matthews (which became Glynn’s) Chez Pierre. It was fun walking down Main Street then. Now? Meh!
It was funner in the late 50s and 60s! And on a bike….
oh wow. this was fun! i so totally remember all those places! thanks!!
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The mural from the Townly restaurant is behind the check out counter in Banana Republic. It was discovered after Klein’s closed and the building was being renovated.