Okay, Portland route recommendation time..
Before getting into specific GPS tracks and turn-by-turn directions, let's talk generalities.
Real riding in Portland starts on the other side of the rivers. Close-in, that means crossing the Willamette and heading into the hills. Out east it means crossing the Sandy and heading into the Gorge or the foothills of Mt. Hood, and to the South, it means crossing the Clackamas, Tualatin, and/or Willamette to get further outside the limits of sprawled suburbia and into farmland and forests. Amazing riding exists in wine country beyond the western edge of the Beaverton/Tigard/Wilsonville suburbs, it's just a bit far to get to from Portland proper without a long transfer through somewhat boring sprawl - unless you are driving out there or want to spend an hour on the MAX to get to Hillsboro to start your ride. There is of course some interesting riding in SE/NE Portland and plenty of coffee shops to visit - it's just not stuff that I'd prioritize an entire day or ride around given limited time visiting the area. If you just have an hour and you want to see more of the city, it's easy to map out a Mt. Tabor, Rocky Butte, NE/SE ramble, all in the comfort of bike lanes and greenway streets.
I'm going to focus here on riding in the West Hills since that's the most accessible option for someone staying close-in, and offers enough diversity and interesting stuff to spend a few days exploring without too much repetition.
By starting anywhere close-in on the East or West side of the river, you have plenty of options for coffee - some favorites of mine are Nossa Familia and Water Ave in SE Industrial, Upper Left near Ladds Addition, and Good Coffee in Slabtown/NW - plus Morse in Lake Oswego. Warm up the legs a bit, get caffeinated, and head for the hills!
Within the genre of West Hills riding, there are roughly three options or styles of rides to take in:
(1) the leisurely but somewhat climby jaunt to Lake Oswego (LO) that takes you on a multi-use path, up through a cemetary, winding through the high-rent district, and around a lake lined with bougie palaces -- it's a very approachable way to see some of the riding here and can be expanded into something with a frightful bit of climbing by going a little south, or simply have more miles tacked on by venturing further west or N/NW;
(2) the silly cutty mish-mash of 20% artisanal pavement climbs up down around and over the closer-in parts of the west hills, many of which are incorporated in the Ronde PDX rides (
http://rondepdx.com/) - this is the stuff I love and never grow weary of riding - it's safe(ish) due to the low overall speed of traffic in these areas, it offers incredible views, physical challenges, and endless variety - and at times you can be a few hundred yards from a freeway and feel like you're in the boonies - it's the riding that makes Portland such a great place to be a cycling enthusiast;
(3) venturing further afield into the far reaches of the West Hills along Skyline Blvd, where you'll find wonderful views, swoopy descents, longer climbs, trolls under bridges, and delightfully unrefined convenience stores.. mixed in with suburbs, soccer moms, squids on motorcyles, and single-wides in the woods burning their trash - this is the other stuff I love about riding in Portland - you can get way out away from everything in under an hour, have a huge adventure, and be back in time for lunch.
So, with the appetite whet - up next are some solid options for rides that fall into each of those three categories.