Not from Portland, but visit there regularly. Can't comment on wineries because I haven't done any in the area for several years. Restaurants I like include Pok Pok, Toro Bravo, Tabla, Paley's Place, Laurelhurst Market, and Cafe Castagna, although I'm not sure about taking a 15 month old to any of those places; also to consider: some don't take reservations. Podnah's has good 'cue and Nostrana has decent Italian but their service is spotty. There are also some micro breweries that may interest you. For bread & baked goods I like Ken's Artisan Bakery;
St. Honore is good too, but I like Ken's better.

For something different, Powell's Books is a huge store and worth checking out.
“You're dazed, bewildered, trapped in a world without time, where sound collides with color and shadows explode.”