Comfort Food at a Gastro-Bistro

Looking for date night dining on a budget in Portland for meat-lovers? Or maybe a great comfort food brunch? Green gravy for Saint Patrick’s Day? And and and….? 

We recommend the Leaky Roof for meat lovers (but if there’s a vegan onboard, you might look elsewhere).

The hometown vibe and cheerful faces make the Leaky roof a perfect place to take a date if your wallet is slim and you aren’t trying to impress with flash. This is a hello, hi there, come-on-in-restaurant, so even the most introverted companion will feel welcome and at ease.

The Leaky Roof has comfort food menus from brunch through dinner.

Violet Asanovich opened The Leaky Roof over 70 years ago in 1947. The gastro pub started off as a “diner cart” in the Goose Hollow neighborhood, but has since transformed into a popular restaurant with local beer, wine, and food. Despite years of urban renewal like the construction of Interstate 405 in the 1960s, the Leaky Roof has stood strong and continues to serve regulars from every generation. Looking for  Chicken and waffles, shepherd’s pie, or meatloaf? Whatever comfort food you fancy, you can find it all under one roof. And no, it doesn’t actually leak.

“The Leaky Roof is like coming home. When I walk in, I feel like I’m at home. I go home and then I come home to work.” Denice Carver, manager, The Leaky Roof


🥰 Why we love The Leaky Roof restaurant

  • Cost – you can take a date here to experience Portland character and not break the bank
    everything on the dinner menu is under $20 dollars
  • Taste – it’s comfort food with an upscale twist
    grease won’t drip off your (or a companion’s) beard
  • Brag – it’s a local business, e.g., eat, drink and support local
  • Experience – fun dining, indoors or out
  • Extra – holidays are celebrated here
    expect yummy green gravy on Saint Patrick’s day


Very little here for a vegan or vegetarian


For the meat lover
Shepherd’s Pie
What goes better with beef than a Guinness broth and mashed potatoes?

A side of Rosemary Biscuits & Butter
Why? Hello! Rosemary!

It’s also a good place to go for Brunch in Portland

The Leaky Roof serves an excellent brunch
Saturday & Sundays (9am-2pm)


  • Belgian Waffle
    Light and fluffy waffle topped with whipped cream and fresh berries, served with butter and syrup
  • Chicken ‘n’ Waffles
    Fried chicken breast, light and fluffy Belgian waffle, served with butter and warm syrup

  Must-Try: a side of Rosemary Biscuits & Butter


And a good place to go for Happy Hour in Portland

The Leaky Roof has great Happy Hour Cocktails, whiskeys, and wine. With a side order of good bar food, too.


  • Tito’s Mule a.k.a. the Texas Ass
    Tito’s Vodka-Lime Juice-Ginger Beer-Lime Garnish
  • Spring Chicken a.k.a. the Hendo
    Wild Turkey 101-Angostura Bitters-Lemon Juice-Simple Syrup-Ginger Beer
  • “Goose” Hollow Cosmo
    Grey Goose Vodka-Triple Sec-Lime-Cranberry
  • LR Margarita
    Hornitos Reposado Tequila-Muddled Lime-Grand Mariner-Salt Rim

1538 SW Jefferson St.
Portland, Oregon, 97201


The Leaky Roof

By Bridgeliner Creative Studio
The Bridgeliner Creative Studio helps clients big and small engage locals, through campaigns that use creative marketing, storytelling, events, and activations to build community, conversation, and impact.