I'm new to the group and have been spent the last couple of weeks immersing myself in all the resources this site has to offer, as well as nwhikers.org and Alltrails.
About 10-15 years ago my wife and I would regularly hike the popular hikes in the area (Eagle Creek, Dog Mountain, etc.). For our honeymoon in 2009 we did a 7 day hike around the Dingle Peninsula in Ireland.
We haven't done many adventurous hikes over the last decade or so, but I do take our dogs and 5 year old son (when he isn't sleeping in) on 2-5 mile hikes every morning around Portland. Powell Butte, Mt. Tabor, and Oaks Bottom are part of our regular rotation.
Lately I've been feeling the urge to expand our adventures again and set the goal to do at least one new and more challenging hike each month this year. Most of these hikes would just be myself and the dogs. As a stretch goal, I'd like to aim for at least one multi-day hike in the fall.
After venturing out on a couple of new hikes over the last couple of months I have realized a couple of limitations though.
1. Our two current dogs are both young, large, enthusiastic, and rodent-obsessed. We're working on training, but not ready for narrow trails along risky cliffs just yet

2. Our car and my driving ability are also limiting factors. We have a Honda Fit and I'm not really experienced/confident driving in snow or on extremely rough roads. I enjoy hiking in the snow, but I'd rather not deal with chaining up the car or worrying about icy roads.
This is the list of potential adventures I've compiled so far. Any additional suggestions or advice would be much appreciated!
Mt Hood
https://www.oregonhikers.org/field_guid ... _Park_Hike
https://www.oregonhikers.org/field_guid ... d_Cap_Hike
https://www.oregonhikers.org/field_guid ... Trail_Hike
https://www.oregonhikers.org/field_guid ... adows_Hike
Eastern Gorge
https://www.oregonhikers.org/field_guid ... Trail_Hike
https://www.oregonhikers.org/field_guid ... ntain_Hike (the description for this one describes rough roads, but recent comments on AllTrails claim the road has been graded and improved)
https://www.oregonhikers.org/field_guid ... kitat_Hike
Indian Heaven Wilderness (potentially a good place for first backpacking trip?)
https://www.oregonhikers.org/field_guid ... dd-on_Hike
https://www.oregonhikers.org/field_guid ... apiki_Hike
https://www.oregonhikers.org/field_guid ... _Loop_Hike
https://www.oregonhikers.org/field_guid ... _Loop_Hike
https://www.oregonhikers.org/field_guid ... _Loop_Hike
Obligatory hiking companion photos: