No Squid in This Deep River
Calamari’s Tavern, Deep River
October 2026
This website and my CTMQ mission is over 20 old as I write this. That’s pretty old for a little passion project. I’ve personally made the trip around the sun nearly 54 times. The current owner, Russell Calamari, Jr. has owned and run this place for the same amount of time I’ve been alive. But 20… 54… that’s nothin’. Calamari’s Tavern has been in operation in Deep River since 1933. And it has always been owned and run by the Calamari family.
I believe they are human, by the way, and not squids.
Back when I started this site Connecticut issued different types of liquor licenses, and one was the Tavern license. The main feature of this license, other than it being relatively cheap, was that tavern’s couldn’t sell beer or cider with an ABV over 6%. I don’t know if liquor was even allowed. All of this was made obsolete in 2020 (I think) and we lost part of our history. The “true taverns” were no more, and several closed during or as a result of the pandemic.
A few remain, although they now hold cafe licenses and serve booze and higher potency beer. But the thing is, the patrons that have been going to places like Calamari’s are perfectly happy with their cheap drafts and low ABV American lagers. I have no idea how long these holdouts will remain in business, but if I had to bet which one would last the longest, I’d bet on Calamari’s.
I stopped one Friday afternoon and unfortunately didn’t have much time at all. I would have liked to have stayed much longer, enjoyed a hot dog and a habanero hard boiled egg, lingered over my beer, and perhaps chatted up the locals. But this volunteer work of being the guy trying to experience everything interesting in Connecticut does not allow for much dilly-dallying.
(That’s not remotely true, but on this particular day at this particular time, it was.)
The Main Street building presents as a house. The building is old, built in 1840. The building once housed the company store for the adjacent piano factory. The building has stories. You can feel it as you walk in through the screen door. Yes, there’s a screen door.
No one paid me any attention as I bellied up to the bar other than the bartender. Two Harley riders to the left of me, what appeared to be town sots and a younger woman to my right. Eyes were focused on the one small TV at the end of the bar showing a hotrod auction show. “Miller Life bottle, please.”
Four bucks later, I began to absorb my surroundings. Going back to my first paragraph, can you believe the current Calamari has been running his bar since 1973 or so? I cannot believe that. (And I don’t have any idea how day-to-day he is now in 2026, but he is still the name on the liquor license. Much of my historic information comes from a 2014 Courant article that, as always, I’m not going to link because it won’t work for you anyway.)
So I’ll say that Russell, Jr. is still hands-on and has been running the joint for 53 years. Before that, it was his father and namesake, and before that his grandfather, John Jacob Calamari, who opened the tavern in 1933. And if you somehow forget how old this place is, there are reminders on every wall in the form of old newspaper headlines from World War II such as “GERMANY GIVES UP,” and the like. Antique beer ads and signs pop-up here and there as well. The wooden furniture is original(!) and the wooden floor is curved under the millions of footsteps that have trod upon it. The cash register is ancient.
In fact, according to that Courant article, a liquor license from 1936 that hangs on the wall predates a town name change and lists the tavern’s locale as Saybrook – the town’s name was changed in 1947.
After walking around the small space, I settled into my bar seat and just… listened.
“What do you call a lesbian eskimo?”
“A klondike”
No one really laughed, and the joke teller explained that he enjoyed the joke because it was silly and not dirty. A woman came in and ordered a Rum and Coke. The bartender heaved a 1.75 liter handle of rum and poured it into a cup. I’m mentioning this because it is absolutely legal to pour drinks directly from these large bottles in Connecticut (You just can’t “marry” them). When I double checked the laws – which, if this wasn’t legal you would not be reading about it because I rather like the Calamari’s Taverns of the world – the “AI assist” gave me the following tidbit of information:
A bar cannot give the entire 1.75-liter bottle directly to a single patron for their own consumption, as state regulations limit service to a maximum of two drinks per person at one time.
This is your reminder that AI is, at it’s core, stupid.
The patron grabbed some dice and rolled them, didn’t hit whatever she wanted to hit, and therefore had to pay for her drink. That’s fun. She had no money and promised to pay the bartender later after she was “off of work.” Hey, sometimes we need a stiff 2 PM drink to get through the day I guess.
I was clearly an outsider, but didn’t feel like it. I’m sure I could have had long conversations with everyone at the bar, but alas, much to my dismay I had to go after my one “Champagne of beers”. Deep River is a lovely little town, often overlooked as it sits between the more bustling Chester and Essex. There are breweries and bars in those towns, but sometimes I’d much rather hang out and spend a few hours in Calamari’s Tavern instead.
And next time I’m down here, I will.
CTMQ’s visits to the last Taverns of Connecticut
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