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Pleasant Cafe, Roslindale MA – “Wicked Pleasant” Since 1937! Top 10 Massachusetts Retro Roadmap Destination!

Posted on: January 12, 2018

  • Address:: 4515 Washington St, Roslindale, MA 02131
  • Phone: (617) 323-2111
  • Web:
  • note: Huge free parking lot across the street!

I am so excited to share the Pleasant Cafe here on Retro Roadmap because it truly embodies everything on my mental “what makes a place Retro Roadmap- worthy” checklist. While each place I share has some of these elements, it is rare to find a destination that has all of them.
This is why The Pleasant Cafe is now in Mod Betty’s Top 10 Massachusetts Retro Roadmap destinations!
Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

Family Owned and Run!

Opened as a restaurant in 1937 by an Italian family (the 4 Iantosca brothers), it has been in the capable hands of the Morgan and Lynch families since 1979. Like any true family run establishment you’ll always find a family member here. I spoke with John Morgan (whose dad was the original Morgan in the Morgan/Lynch partnership) and his wife Joanie and you can just tell the love they have for this place. Their kids help out in the kitchen on occasion so I’m cautiously optimistic that the next generation appreciates how special this place is.

Authentic Vintage Charm. EVERYWHERE!

All of the vintage elements here are the real deal, not some internet-bought faux history slapped up to fake that this place is from an earlier era. It just IS. And it is awesome!

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

Super extra bonus points for those fab vintage Christmas candelabras!

The stunning 1940s-era swirled glass brick facade diffuses the light from the inside, casting a warm inviting glow above the slate tile apron. The neon Liquors sign in the window on the bar side is a treasure from the earlier era and the vintage photo below shows the other windows had similar neon signs (Pickwick Beer,  Ballentine Ale along with Fine Foods and Famous pizzas) While this sign may make you think that this is just a bar, rest-assured this is a rest-aurant (with a bar) and is completely family friendly.

Pleasant Cafe Roslindale MA Vintage Photograph

photo courtesy of the Pleasant Cafe

Interesting Aside! The original 1949 sign, installed while the restaurant was run by an Italian family had a shamrock on it (Mod Betty, being ½ Irish thinks this icon might’ve been shorthand for “this is a place you can get a drink”) However, now that Irish-Americans own the restaurant own it, the shamrock has been replaced by a circle shaped like a pizza. You’d think it would’ve been the other way around! 🙂

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

The exterior marquee type neon sign was added in 1949 and is one of the few remaining vintage neon signs in the Boston area. Happy to see that John and Joanie have done away with the protective plastic seen in this 2008 photo on Flickr, and are keeping this beautiful sign in good, glowing shape!

Clean and Well Kept!

The Pleasant Cafe’s authentic vintage charm extends to the inside, where it is well kept and well loved.

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

View from the Pleasant Room at the back of the bar side – without those TVs you’d be hard pressed to know what decade this is!

Here you’ll find actual wood paneling (not fake) leather booth seats, Formica topped tables. As many of us who own older homes know, sometimes keeping the old stuff in good repair is more challenging (and expensive!) than starting from new, so my Retro Roadhat goes off to The Pleasant for doing the right thing and maintaining their vintage decor instead of chucking it.Pleasant Cafe - Roslindale MA - Retro Roadmap 2018Many new places try to buy instant authenticity by slapping reproduction old signs up on their walls, but there’s no way you can ever replicate the visceral “stepping back into the past” feeling you get when you are surrounded by walls and fixtures that have absorbed the stories, sounds and feelings of the last seven decades. It is a such rarity these days to find a place so well preserved like this, that I consider it a treasure as it allows all of us to feel what it must have been like to go out to eat before the chains and franchises took over.

A Pleasant Menu!

Most of the menu at the Pleasant hasn’t changed in decades, nor should it. They still offer many of the Italian-American originals from the Iantosca era but there are many classic restaurant staples to order. Sandwiches, salads, soups and entrees, everything is made fresh, and there’s something that’s bound to satisfy any palate (Except kale lovers. I happily did not notice any kale on the menu!)

The Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

Many of the the daily specials are a nod to the comfort foods of the Boston area – Boiled Dinner, Scallops, Yankee Pot Roast, Prime Rib, Fish on Friday, Grapenut Pudding. My dad would’ve loved this place.

But the food that evokes strong emotion is their pizza.

The Pleasant Pizza!

Using the original recipes from the Iantosca days for dough and sauce, with their special cheese blend, pizza is served daily from 3pm on (noon on Sundays). This gives the dough (made daily) a chance to rise, and the ovens to warm up. Their thin crust has a crackling outer edge and can be loaded with a whole host of toppings, from standard pepperoni to exotic eggplant or pineapple. We went all the way with old school Onions and Peppers, and MAN did it hit the spot!

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

Too big to fit on our table!

Mod Betty,  with her old accent ringing in her ears declares this to be “wicked pissa pizza”!

The Bar at The Pleasant Cafe

The bar at the Pleasant has its own front entrance but you can also access it through the dining side. Here you can sit on a swivel stool at the long wooden bar or choose one of the booths if you want to dine on this side.

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

There are a few TVs on this side to keep up with local sports – Go Sox!- or in our case to watch a winter storm approaching. A classic Boston touch is the portrait of JFK hanging here. I used to see this famous portrait everywhere. And I would not be surprised if those horns are the same ones as shown this great black and white photo of the old bar, via the Roslindale Historical Society.

Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

They’ve added some craft beers, wines and more modern specialty cocktails to their drinks menu, but Mod Betty’s heart sings at the extensive list of cocktails available here. Seriously, cocktail pals ( hello Brother Cleve!) you could follow “the timeline of the popular cocktail” using this list as reference – From Grasshoppers and Harvey Wallbangers to Old Fashioneds or Ward 8s and so many more (thanks to Hidden Boston for their photo links.)
Mod Betty vacillates between tippler and teetotaler depending on the day, but I’m tempted to try and drink my way through their list, ordering a different cocktail at each visit. Who’s with me?!

Interesting Aside! The Pleasant sadly lost their bartender of 70 years, George Parelli when he passed away in 2015, but here’s a video interview with him in 2008, reminiscing about the Pleasant back in the day:

The Pleasant Room

At the back of the bar section is the Pleasant Room which is open for larger parties, Little League events (or as Mod B keeps calling it “Miniature Baseball”) and any type of gathering you’d like to have here. It warms my heart to no end to know that little kiddles will have “Pleasant” memories of having pizza and fun here, and my hope is that they continue to come here, to ensure the future of this landmark place.
The Pleasant Cafe Roslindale MA - Retro Roadmap 2018

Interesting Aside! The Pleasant Room was originally the kitchen when the restaurant first opened. Pizzas were made in the basement, and the orders were delivered to the cook via a pipe system; the order slip would be placed in an empty juice can (remember those?),  which would be put into the pipe and sent down to the lower kitchen, and the completed pie would be hoisted up to dining level via a dumbwaiter!

The Vibe

The thing I love about the Pleasant is that while you can tell it’s a place where locals frequent, first-timers like Mod Betty and her pals are made to feel right at home, right away. Many of the waitstaff have worked here for years and years, and their attentive yet not fawning service will make you feel like a regular by the time you leave. Again, this is the authentic real deal – not some corporately mandated “make the guests feel welcome” program with insincere smiles and canned catchphrases.

The Pleasant Cafe - Roslindale MA - Retro Roadmap 2018

Can you see why Mod Betty has declared this her neighborhood haunt, even though it is nowhere near her neighborhood? I’m making a commitment to visit The Pleasant Cafe whenever I’m in the area, and if you’re local, you need to make The Pleasant part of your regular places to visit. If you’re “from away” you can drive here and easily park in their free parking lot across the street, and experience one of the most Retro Roadmap worthy places Mod B has ever had the chance to share with you all!