Guide To The Best Dive Bars In Southwest Connecticut c. 2016

Lou Gorfain

Dive Bars aren’t necessarily dives.

Take Casey’s Tavern in Stamford.  Secluded on a dead end side street just off downtown, its windows are veiled, its entrance shadowy.  What’s behind the curtains? 

Well, step inside and be amazed.  The crowd is convivial, the decor beguiling, and the joint jumping.  A song blasts on the juke, but it’s buried under the laughter and yak.  Behind a highly polished hardwood bar, mirrors and bottles glisten.  Out the back door, a sun-splashed patio beckons.  And on each table – there’s an extensive menu to ponder.

So is Casey’s a dive?  

“No, no,” Seamus Costigan tells us. ”We don’t attract trouble.”   He should know.  Costigan is not only the guy behind the stick, but the affable owner of this Irish pub.  It is said once Seamus meets you, he never forgets your name or your drink.

These days the term “Dive Bar” doesn’t imply bikers, broken bottles and bloody bathrooms.  Rather, a true Dive serves as a neighborhood gathering place, where regulars can dive in*, grab a quick (or long) one at an affordable price,  shoot pool or darts,  argue sports and politics, or just b,s. about life and love.  No one comes in to be lonely … or leaves broke.  

When you belly up to the bar, there’s no need to order.  The ‘keep is already pouring.  

Seamus nods and grins. “I guess we’re a dive bar, then.  I know exactly what time my regulars come in, their drink, and what they eat.”

In a modern Dive, the food is as much a draw as the liquor and the laughter.   So forget about microwaved burgers and dogs, stale chips, or soggy Slices.  The new breed Dive caters to customers who aren’t just thirsty, but hungry for a tasty meal without breaking the bank.   

Gourmet dining? At times.  Complexity, not really.  But solid eats, definitely.  In fact, some dishes are farm fresh and healthy. 

Herewith, we curate the best eats we found at some selected SW Connecticut Dives …

BILL’S CROSSROADS   --  12 Tunxis Hill Rd., Fairfield  

A buddy and I stopped for lunch and claimed the last two chairs at the busy bar.  From a whiteboard menu I ordered a warm roast beef sandwich, rare.  My friend, a connoisseur of Philly Cheese Steak, cautiously chose that.  

The bartender brought an ice cold bottle of beer for me and a glass brimming with chardonnay for my friend. “We don’t skimp on anything here,” he proudly announced.  He was more than right.

The hefty portion of roast beef he next placed in front of me was as generous as the wine pour – a mountain of meat lightly bathed in a velvety red sauce, stacked high on a fresh, oversized roll.   The middle of the slices were deep pink, surprisingly rare.  The bite was tender, the texture moist, and the flavor deep.  Despite the heavy sauce, the roll retained its crispness.   Bill’s RB was as sumptuous as any deli sandwich I’ve ever been served, so massive I had to bite at an angle.   The amazing price: $5.99. 

As for the equally prodigious Philly Cheese Steak, my friend thought it was better than Geno’s, but not as fantastic as Stackey’s, his favorite steak stand around Philly.  But far better than expected.

Midway through the meal, Eddie announced, “Jason’s got a round for the bar.” We wondered what the occasion was.   “At Bill’s,” the guy next to us explained, “we take care of each other.”  

It was a theme found in most of the dives we visited, with the exception of…

BLACK DUCK CAFÉ – 605 Riverside Ave.,  Westport

It’s a dilapidated dive perched on a barge under a bridge, with a slight tilt portside. The bartenders are gruff, the seating and service sluggish, but the 20 choices of succulent hamburgers make the wait and the rudeness more tolerable.  

Until discovered by Guy Fieri on Diners, Drive Ins, and Dives, Black Duck was a just a neighborhood joint that catered to a lunch crowd and commuters from the nearby train station. Today it’s a jam-packed tourist attraction and foodie destination.   In his yearly roundup, CTBites’ Jeff Schlesinger has crowned its bar burger as one of the best in Fairfield County.  

Though it’s been a while since he’s had one, “Jfood” feels their 6 ounce 80-20 Angus burger, cooked precisely to order, is excellent. We agree.   Like Fieri, we loved the juicy Doctor Proctor’s burger, its medium rare heart melting with bleu cheese.   As any Steakhouse devotee will agree, Beef and Bleu is a marriage consummated in carnivore paradise.

The Black Duck was named after a speedboat which had been named after a rum runner boat.  It’s literally a watering hole on the water.  That said, beef rules over fish.  We found the deep fried seafood a bit too greasy and overcooked.  

Fortunately, those burgers make up for many sins.

BRUCE PARK GRILL – 231 Bruce Park Ave., Greenwich

A dive bar just a stone’s throw from tony Greenwich Avenue?   Yes, but you’ll find no Birkin bags or Manolos here, just blue collar Joes and Janes, and regulars from the neighborhood, like former Met and Greenwich native Tim Teufel.   (He used to down a few here with Seaver.) The place is a local institution, the last bar of its kind in town.

“BPG,” as the natives nickname it, is renowned for two features.

The first is a regulation wooden shuffleboard, 22 feet in length, which dominates one wall of the room.  Anyone approaching the pristine table with a drink in hand is instantly body blocked and chastised.

The bar is equally as famous for its thin crust Bar Pizza, a charred and cheesy delight, served on a small paper plate, and sized not to share.   Priced at 7 dollars, with a dollar tariff for each additional topping, it’s probably the best bargain in a town not known for being easy on the wallet. 

Reminiscent of the more ballyhooed bar pizza at Colony Grill, the pie bears a load of tomato sauce not found in Stamford and Fairfield.    Greenwich folks usually prefer BPG’s version.   Elsewhere, aficionados opt for Colony.    Both are good.  While we prefer Colony, Bruce Park comes at a fraction of the price.

The “Sometimes Steak” sandwich came highly recommended.  Meh.   We wondered how it earned the name.  “Sometimes we have it,” the Bartender explained.  “Sometimes we don’t.”     If they don’t,  Greenwich Prime Meats across the street sells a  magnificent steak sandwich made famous at the late and lamented Manero’s.    

CASEY’S TAVERN –  85 Woodside Ave., Stamford

Named for Seamus Costigan’s beloved grandmother, Casey’s ranks as a true Irish pub, a hidden gem more authentic than the heavily promoted Tigin’s on Bedford a few blocks away.  Most of the staff speak with a deep brogue, and Guinness reigns as the brew of choice.   But you don’t come to Casey’s to just drink and socialize.  You also enter to eat.

Though tempted by the Shepherd’s Pie, we couldn’t resist ordering the Traditional Irish Breakfast and a Guinness.   Only one word properly describes the breakfast and the beer:  hearty.  The plate was layered high with fried potatoes, black and white Irish pudding, mushrooms, tomato, thick bacon, Irish sausage, a pair of fried eggs and buttered toast, and a bowl of baked beans to the side.    

We dove in.  A half hour later, we finally finished a meal that would supplant breakfast, lunch, and dinner that day and part of the next.   Fortunately, quality matched quantity.

At one point, Costigan suggested dipping the potatoes in a curry.  Indian curry on an Irish menu?     “In Tipperary, fries and curry are what you have the Morning after,” he explained.  “It’s the Irish cure for a hangover.”   Think of it as Gaelic Poutine.

There are nearly a hundred items on Casey’s extensive menu.  A couple that have been recommended by patrons are the Battered Sausages in garlic mayonnaise and an Irish Stew, in which on the bone lamb, potatoes, carrots, celery and onions swim in a thick rosemary stock.

We’ll return.

CHERRY STREET EAST –  45 East Ave., New Canaan

The story is straight out of Frank Capra.  When its Home Town Pub burned down 10 years ago, the New Canaan community banded together with the owners of Cherry Street East and built an exact replica of the beloved bar.   

New Canaan may be a fashionable city that hosts more fine restaurants per capita than any in the state, but CSE occupies a special place in its pantheon.  Step into Cherry Street and it’s A Wonderful Life.  Everyone appears to know each other, kids dart around, and at the “elbows on the table” bar, gas station attendants joke around with Hedge Fund managers as they share a pitcher of Bud.  

The menu is pure Middle America as well.  Steaks, fish, chicken for the grownups, Mac and Cheese for the kids.   But whenever we drop in, we crave only one dish:  “The Cherry Street.”  That juicy, flame flavored burger ranks with Black Duck’s Bleu Cheese as the most delectable bar burger we tasted in this survey.

Fire grilled, the 8 ounce burger comes to the table hatched with sear marks and resting on a toasted English muffin.  It’s a roll that easily stands up to the half-pound hand-formed paddy, the muffin’s crooks and crannies running with juices.   A number of toppings are available to build the burger, but we keep it simple with grilled onions and peppers.   As a side, we like the sweet potato fries dipped into a sour cream dressing, but regulars highly recommend the onion rings. 

As we left, the family at the next table waved good-bye, and a lanky fellow at the bar winked.

Had to be Jimmy Stewart …

DEW DROP INN – 25 North Ave., Derby

Wings are standard bar food fare.  But at Dew Drop, those airfoils soar to new heights. When we came in, the house was packed and beer was flowing from the 21 lines behind the bar.  Almost every patron was snacking and smacking on wings.  

They had over 100 different styles to choose from: sweet American Peanut butter and Jelly (a favorite) or tangy Asian cucumber wasabi, or Strawberry Habanero, or even Dessert Wings, coated with delights from Nutella to French toast.  So who creates the combos?   Our server said the line cooks come up with the concoctions, and then taste test them with the all-lady bartenders.  Once the owner gives the final nod, the new wings can fly.

We chose the Parmesan, Bacon, and Garlic wings.  The bacon bits and cheese, ladled over a basket of wings, were sensational by themselves, an amalgam both savory and sweet.  But the dressing achieved new heights when paired with the poultry: its skin crisp, its interior moist.   

Without hesitation, these were voted the best wings our group had ever tasted.  Check the web for further accolades.  There’s no other place in America that offers as large and varied a selection of wings.  Buffalo, you’ve been topped by Derby. 

The diverse crowd inside was enjoying a laugh-filled Saturday afternoon blast, far more cordial and light hearted than  expected. We had been warned that Dew Drop was a home for “scary” bikers.  But someone pointed out that when last seen, these tough dudes were doing a Toys for Tots drive in the parking lot. 

So do drop in.

THE LUMBERYARD –  2 Main St., Redding

Georgetown marks the point where Redding, Wilton, Ridgefield and Weston meet. And The Lumberyard Pub is the place where many of the residents from those towns also meet, a colorful neighborhood hangout.   

Folks and families come to the Yard (named in honor of a former lumberyard on its site) not just to drink, but watch sports, play pool and table hockey, dance to local bands, and drink and dine inexpensively.  Especially on deal nights early in the week.

Oversize wings (35 cents apiece until they run out on Wing Night) are a feature of the house.  We found them tasty, but not on as high an echelon as those at the Dew Drop Inn in Derby.  On wine night, spend more than twenty dollars on food, and get a free bottle of grape. On Hamburger night, all burgers are half priced.

Bobby, our waitress (now a co-owner), recommended the Patron Favorite burgers.  Out of the five specialties listed, we chose a medium rare Hellfire: a half pound Angus Prime paddy topped with house made spicy chipotle sauce nestled in a warm, soft bun.  The kick came layered.   A peppery jack added heat, and sliced jalapenos delivered further fire.   The hand formed burger was cooked to juicy, pink perfection.  A tasty blend of flavors and textures.  Highly recommended.  Or build your own burger with a protein of choice -- prime ground beef, turkey, or veggie – and an array of toppings.  You can substitute a pretzel roll or wrap for a regular bun.  

Originally designed as a sports bar by founders and co-owners Mike Sutila and Sandy Pope, the Lumberyard features sports regalia on its walls.  But amongst the Americana, a curious street sign reads “Mary Kings Close,” which is an ancient underground alley in Edinburgh.  The placard is actually an homage from Mike and Sandy to their beloved Scotland, its Celtic beauty and history, and its storied pub tradition.  

MATTY’S CORNER – 2815 Farifield Ave., Bridgeport

A lively bar scene plays out along “The Ave” in Black Rock.  All manner of drinking establishments line either side of a few blocks, and the weekend pub crawl is legendary.    Ground Zero for this bacchanal is Matty’s Corner, strategically situated at the crossroads of Fairfield and Brewster, the heart of town.  Without quarrel, everyone agrees that Matty’s is the truest dive along that stretch.  

The décor inside and out may be a bit dingy, but the place rollicks. Hugs and fist bumps everywhere.  The front door rarely closes, even on a Sunday afternoon, when our group entered the mobbed pub for the first time, but were welcomed like regulars.

Yes, we missed the Friday free Happy Hour buffet.  And we were a day late for Martha’s Saturday Special, $3 roast beef sandwiches.  Nonetheless, the prices on the menu board seemed from another century.  A corn beef sandwich listed for $4.50;   $3 buys eggs and bacon on a roll; a dog goes for 2.50.     Bobby at the next table introduced himself and gave us the lowdown on the scene, the food, and Black Rock lore. He knew everyone in the place, most of them local and many native “Rockers.”  

As for food, he said Matty’s was good.  But the time to come is when Danny, who owns the place, works the kitchen.  Unfortunately he cooks during the week, not on Sunday.   At Bobby’s suggestion, we went for the eggs and bacon.   Tasty, but not outstanding. 

Matty’s is not about the food.  But the party.  If you’re thirsting for a real dive, where the drinks are strong and cheap, the laughter loud, a world where no one is a stranger, Matty’s Corner is sure to quench your appetite. 

SEASIDE TAVERN – 891 Cove Rd., Stamford

Located on a sketchy block in Stamford’s Cove, Seaside Tavern seems, at first blush, every bit a rundown dive.  But inside it boasts a warren of rooms: two bars, a dining room, game rooms, a dance floor, a living room with televisions, and an outdoor patio in the parking lot.  A well-known music venue, Seaside attracts a boisterous nighttime crowd on weekends, hailing from many parts of Connecticut.  They come to dance, drink, game, and matchup.    A Burgers, Wings, and Slice set.

But drop in at lunch or dinner time, and the hormones aren’t as raging, the dining more diverse.  The crowd is older, more local, and hungry.   In fact the rousing conversation at the bar the evening we stopped by centered on the efficacy of a reverse sear in grilling a steak.  

The menu has recently narrowed its focus. Where once 20 sliders were featured, only 4 remain. A number of sit down Big Plates make the list, from a buttery Porterhouse to a Grilled Pork Chop accompanied with apple jam.    

Given Seaside’s name (it’s located a couple of blocks from Cove Park and Long Island Sound), we thought the menu would feature more seafood, but it only offered standard fare: chowder, clams, fish and chips and crab cakes.  Though assured the fish in the chips was fresh, not frozen, cod, instead we opted for a crab cake salad, and managed our expectations.  

However, when the bartender brought the salad, we were impressed by the presentation. The summer greens were fresh, shimmering in a balsamic dressing, and covered with the browned hunks of crab cake.  Our first taste did not disappoint.  While the crab was a bit over-breaded, the balsamic married the meat and greens, which balanced each other in taste and texture.   We complimented the bartender.  He smiled and allowed that we had ordered the healthiest item on the menu.   And probably the tastiest one.

SEVEN SEAS –  16 New Haven Ave.,  Milford

No question, “The Seas” epitomizes a dive.  The grim, ivy covered saloon near the Milford harbor is over a half century old, the decayed floors creak, there’s no parking, and both the seating and the beer selections are limited.  Like a film noir gin mill down by the docks. All that’s lacking is a drunken scallywag or two.

 Don’t wait for a table, grab a stool at the crowded bar, and when the tender finally gets to you, order your favorite frosty and the “Seas” signature dish:  a warm, buttery Connecticut lobster roll.   Eventually, you are served three ounces of warm claws and knuckles stuffed into a grilled top cut long bun, flanked by a pile of hot, wedge fries, and a cup of creamy coleslaw.  (If you’re really famished, order their double lob rolls and a couple of beers)

Like the bar, the sandwich is no frills, just lobster meat shimmering in butter, overloading a New England hot dog roll.  But it’s a banquet, each buttery bite washed down with a sip of ale.  Malt, hops, and carbonation perfectly cut the buttery lobster and bread, clearing the palate for the next lush bite.  

 So forget your fancy gastropub.  This is as good as dive (or most any) bar food gets.   Indeed, Seven Seas always earns a spot on our list of the top lobster rolls in the state that gave birth to the New England delicacy.  n.b. the warm lobster sandwich was invented decades ago at a place just steps away from Seven Seas.

TAUTOG TAVERN – 2926 Fairfield Ave., Bridgeport

Welcome to a dive bar that sources some of its fare from local farmers, claims a passion for sustainable growing,  has their burger custom blended by Pat LaFrieda, and buys their ice cream from Timothy’s parlor across the street.  But it’s also a pub where you can devour addictive deep fried goodies so   oleaginous, they instantly coat the gut for a night of boozing.  

At first the place comes off more Brooklyn than Bridgeport.  But it’s just down the street from Matty’s, most of its regulars are “Rockers”, and as another prominent stop along The Rock’s pub crawl,  Tautog certainly qualifies as a dive bar.

Our table ordered a sampling from this eclectic (if not schizophrenic) menu.   We first crunched on pickled veggies swimming in a house made brine.  The pickle juice imbued a gentle fermentation to the strands of cucumber, cauliflower, squash and pepper. The provisions were delicate and delicious.  We were impressed. 

Until the “Loaded Chips” were brought to the table.  This Calorie Bomb arrives fully armed with salty, scrumptious hand cut potato chips, bathed in sour cream and melted cheddar, spiced with scallions, tomato, red onion and mild jalapenos. All this topped with a spicy chili.  We vowed to indulge in just a bite or two.  Rafael, the bartender grinned.  Ten minutes later he removed a rather clean plate, only a scattering of chips left to appease the cardiac Gods.

Next, we sampled an app that reflected the two faces of the menu:  battered, deep fried green beans.   Tautog’s nod to a healthy fry should be served with a wink.  So too, another one of their decent/decadent apps: Brussel sprouts and bacon.

The Tavern’s signature dish is the LaFriedia Burger, a short rib grind. The almost one pound sandwich is served on a wooden board, along with condiments and assorted pickled veggies.   A clay flowerpot filled with fries completes the somewhat hipster presentation.  

We opted instead for a flight of sliders. The Chicken was disappointing, but we were nicely surprised by the Rising Sun.  Hoisin sauce added a Far Eastern note to the burger, but the piece de resistance was an extraordinary ramen bun, made in house.  The baked ramen noodles lent unexpected textures and taste to the burger, a union of two American and Asian classics.  

Our slider of choice was Ol’ Bleu Eyes, a tidy sandwich of beef, sharp cheddar and Jack Daniels sautéed mushrooms.   Aside from the Jack, how does it honor Ol’ Blue Eyes?  Turns out the owners of Tautog imported their 120 year old wooden bar top from Hoboken, where Sinatra and his pop used to put them away.  

No doubt their saloon was a Dive.


*According to the Oxford English Dictionary, the term “Dive Bar” derives from a time when drinking dens “were originally housed in cellars or basements … into which frequenters may ‘dive’ without observation.”