Day 1 in Short
John Day Fossil Beds with its eerily colourful hills and amazing rock formations.
Skipping Kam Wah Chung State Heritage (opens in May-Oct), Strawberry Mountain Wilderness (time constraint).
Friday head to Madras, Central Oregon for overnight stay (Sonny's Motel @ $75 with 2 Queens). Takes 3.75 hours so leave at 6pm because we should sleep earlier before 12. This is to save time as daylight is shorter during winter-spring timeframe.
Clarno Unit
From Madras takes 1hr instead of Hillsboro 4.5hrs. Reach there @ 8am.
This is the first unit & oldest (40 million years old) of 3 in John Day and has 3 trails in total of 0.75miles, very short walk. I expect to spend 1.5hours there because you will not only walk but read informational signs, touch fossils, grab pictures.
Best if all done and leave before 10am.
Sheep Rock Unit (lunch I suggest just buy something from Madras)
From Clarno takes 2hrs, we can stop @ Kimberly for snack/fuel/toilet. Reach here @ noon.
This is the second unit of 3 and features the most walks and hikes.
Foree Area - two trails in total 1mile. I suggest we skip since same thing as blue basin area.
Blue Basin Area - take Island in Time Trail 1 hour can finish.
Goose Rock - pitstop for pictures, just on the roadside, 10 mins.
Thomas Condon Paleontology Center/Visitor Center - 1hr plus pictures outside. Suggest to leave before 2.30pm.
Picture Gorge - pitstop for pictures, great rock formation during early evening, pitstop 15mins.
**More details/pics here: http://www.americansouthwest.net/oregon/john-day-fossil-beds/sheep-rock-unit.html
Painted Hill Unit (best during evenings)
Carroll Rim Trail - bird's eye view of the Painted Hills. 1.5miles round trip. (this is more epic)
Painted Hills Overlook Trail - upclose view. 0.5miles round trip. (skip this)
Painted Cove Trail - even more up close. 0.25miles loop, short walk only.
Head to Bend for overnight stay. Takes 2hrs to reach there.
**More details/pics here: http://www.americansouthwest.net/oregon/john-day-fossil-beds/painted-hills-unit.html
Dinner @ Mitchell (only 2 places to choose from). Head to Bend for overnight stay. http://www.sonomalodge.com/ (d $55 the cheapest in Bend) Bend offers cheap motels/cheap bars. From Painted Hills takes 2hours so I expect we reach our cozy motel before 10pm. I will want to go enjoy some drinking like Bend Brewing Co as they have award winning beers but closes at midnight so won't be too late. Join me if you want.
Day 2 in Short
Bend an outdoor lover's paradise (but a lot not accessible during winter time zzzz), lively city with plenty of good food and accommodation.
Skipping Sparks Lake (road closed until April), Proxy Falls (closed by state during winter), Tumalo Falls (4.5 mile hike, time constraint). All which I considered before..sigh.
High Desert Museum (morning)
Charts exploration and settlement of the West, re-enactments of a Native American camp, a hard rock mine and an old Western town. Also has live snake, tortoise, trout exhibits, birds of prey and otters. $15 per person. Exhibits focus on local culture, natural resources, wildlife, and art. Opens @ 9am-5pm. Best to be in the morning for animal interaction.
Smith Rock State Park (after simple lunch)
We try some Asian Fusion lunch @ Soba, main about $6.50 to $8.00 only.
I have not chosen a trail to hike or walk yet. For now more pictures here: http://www.mikeputnamphoto.com/photographs-of-smith-rock-state-park-terrebonne-oregon
Cove Palisades (strictly optional)
I highly doubt we have time if we plan to eat in Blacksmith (see below). Plus Smith Rock State Park has a lot of good short hikes (over 6 of them) like only 1/3 miles so we should spend time there instead. More bang for your buck.
Balik Kampung
Head back to Hillsboro (takes 3.5hours). I want to be back not too late! So I suggest we reach back at 9pm ish meaning leaving Bend around 5.30pm ish. I suggest we have our dinner at their top choice steakhouse Blacksmith offering good value 4 course meal @ $24 which I think 2 ppl can eat. (4.30pm to 5.30pm only)!! http://www.bendblacksmith.com/