The big building in the center of town — at the Post Road/Taylor Place intersection, across from Main Street — has been many things.
It was a pharmacy: first Driscoll, then Colgan’s (below), and later Thompson’s.

(Photo courtesy of Christopher Maroc)
Those were old-fashioned drugstores. In addition to prescriptions, Band-Aids and the like, they sold magazines and paperback books. There was a lunch counter, with a machine to make “malteds” and “floats.”
It was a place where everyone could congregate: mothers, downtown employees, teenagers who walked there after school from Staples High, on nearby Riverside Avenue (now Saugatuck Elementary).
In the 1980s it was a gathering place of a different type: Ships. The restaurant served good, basic food. Ships was where you went to meet old friends, to take a break from shopping, after a movie.
The tables — and bar — were always packed.

(Painting by Al Willmot)
In between it was the site of Eddie Bauer, and a couple of other retail stores. Briefly, it housed a pop-up shop selling Halloween and Christmas gifts, and a 2-week sales outlet for Orvis.
Today it’s Tiffany.
That’s not a place to just hang out. And the prices are far higher than Colgan’s, Thompson’s, or even Eddie Bauer.
But this is the 20th anniversary for Tiffany in town. Their run rivals the drugstores that preceded it.
What that says about the Westport of yesterday and today, I’ll leave up to you.
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Hey Dan, You forgot “Mr. Mailbox” had space just before Tiffanys. I rented it from Marc Kaufman.
Went to Ships with another couple and ordered beer and burgers 🍔. Shortly afterwards another foursome sat across from us and ordered the same. We were still drinking our beers when the other table got their burgers and immediately started eating. We weren’t in a rush and didn’t mind waiting. Later I asked the waitress about the speedy burgers. “Oh, they’re going to the movies and we don’t want them to be late so we do their order immediately.”
Nice 😊
When Tiffany moved in, I posted on 06880, “Well, there goes the neighborhood.”
It sure has.
The picture of Colgan’s Drug Store brings up so many wonderful memories for me. Following the 6th grade graduation from Bedford Elementary School (Now Town Hall) my parents took me to Colgan’s for a soda. It was a big deal. Then on to Bedford Jr. High School just up the Post Road toward Norwalk. Several of us used to walk down from Bedford Jr. High to Colgan’s to get the city bus home. Standing in front of the store and waiting was a time to talk to friends and just maybe having a boy ask you if you would like a soda. It was a time of delight in the simple things of life. Purchasing a soda, probably a coke, was a big deal. To quote a song: “Those were the days my friends, we thought they would never end.” Even three years later attending Staples on Riverside we often chose to walk to Colgan’s for the bus rather than getting it in front of assumption Church. Good simple times.
I remember using Colgan’s vacuum tube testing machine when our TV wouldn’t function on a Sunday afternoon. It usually needed a new 5U4 power tube which they had in stock.
My cousin Barbara, a few years older introduced me to all the cool places in town like Colgan’s and Marvel’s Bakery just across the alley. Great for after school treats.
Oh boy, did I love Colgans lunch counter. My mom would take me there for a soda. What a treat.
Behind it there was a store called Bongs and Jeans, I bought an Aerosmith t-shirt there in the late 70’s. I remember women getting drunk and dancing on the table tops at Ships. Eddie Bauer was very cool. Tiffany’s is classy, personally, I don’t go there. Most of all I miss Schaffer’s sports and the art supplies and Carmen’s pinball and video games… too many memories… also, the many hundreds of people walking around made that corner feel like home. Now it’s just cold and corporate. The blotchy horse is fun, that makes up for the loss. In the end, change is good. I have great memories of shooting up heroin across from Ships at Needle Park as a young child after having run away from home. There was always someplace to go.
Thompson’s was the first stop after WALKING downtown from Bedford Junior High for a cherry coke with fries at the counter. Then to the YMCA for ping pong, pool and a swim. The Wonder Years.
Thanks for reminding me that it wasn’t a plain coke, it was a cherry coke! I’m a bit older so it was Colgan’s in my time….
Thanks for the mention Cuz. Downtown Westport was great for after school in the day. Don’t forget Kleins, the original Oscar’s, Bill’s Smoke Shop and so much more.
I consumed way too much candy purchased or bartered from Bill and Bill’s Smoke Shop in the late 60’s (my best guess, it’s been awhile …) Still wonderful memories.
Bill’s Smoke Shop was to many of us young males an introduction to the world of “Playboy” magazine in the back of the store.
It was also Buffalo Clothiers in the early 70s
We used to walk from Hales Court to Thompson’ s on the way to Bedford Junior, we would buy a bag of penny gum and candies then sell them at school for a profit, “oh those were the days my friend we thought they’d never end” but they did 😎👍