It’s quite possible that the best street in Portland is SE Gladstone. It’s got a great coffeeshop, a cute nursery, and a bounty of solid neighborhood bars. Personal fav on the street though, is Gladstone St Pizza & Saint Pizza Lounge. It is set up like a horseshoe separated by a doorway, one side is family-friendly and the other is the bar area. They also have a really top notch back patio where you can wile away the hours during the summer drinking whiskey or beer and noshing on pizza and mezza platters.
The vibe is super chill. Equal parts cool and not-cool, this place is worn-in and comfortable, and they always have great music playing. Hang out on the bar side for a kids-free neighborhood bar feel, or bring the kids and plonk down in the restaurant side and get comfortable. Personally, I stick to the bar and chat with the totally cool and unpretentious staff.
Okay, now for the food talk. Try everything. Every damn thing. It’s all delicious. My go to is the caesar salad and either the Down South or the For The House. All their pizzas are thin crust and are kind of a less is more philosophy. Keep it to 3 toppings and you should be set up for pizza success.
They are open 5-midnight, but stay open later Thurs-Sat, but there is no real set time for closing. It’s a neighborhood joint. Go with it.