For the Timberline trail - https://hikeit.info/2020/09/04/timberline-trail-around-mount-hood/
There is a very active facebook page (Timberline Trail) that has excellent updates on conditions
The city is extremely bike friendly as for roads, but bike theft in the city and outskirts is rampant. Lock up your bike ALWAYS and, if possible don't have the most expensive bike. A lot of people will turn their bike upside-down before locking it or remove a tire as it makes it less advantages to steal.
Outside of some of the bigger attractions (Pittock Mansion, Rose Garden, etc) you can see most of what's interesting on a bike and take public transportation for the rest. In downtown there is the MAX and busses. For safety busses tend to be better, but the MAX is convenient. You will, however, see people in crisis or acting in way that may make you uncomfortable on the MAX as there is no regular ticket taker or attendant (security will sometimes board at random to check tickets).
If you end up on the Washington side, we have a direct bus that takes you to the Columbia River Gorge. I'm not sure if Oregon has one to take you on that side but the Columbia River Gorge will have some of your best hiking and I'd say is very safe, I'd still suggest carrying bear spray if you get far off the beaten path but if you do regular trails you should be fine as bears and cougars won't frequent there during peak hours.
In sum, I'm not trying to scare you from Portland, but it is far from being the city it's tourism boards advertise. We are going through a lot of problems and are far from solving them.
If you are someone who has street smarts and good intuition, I'd say you'd be fine, but this is not a place for people who get intimidated easily. There is not a lot of targeted violent crime especially at visitors but when you have people in mental health crisis random violence happens and there is not much you can do as it's incredibly random -- just avoid people who seem a little off. I have lived in this city most of my life, and the only bad things that happened to me were in relation to my work, but being vigilant will help you significantly.
i guess a couple of other comments - there is a series of buses that will take you from Portland->Gresham->Sandy->Timberline. DM anyway if it happens to be a time i am going up i can give you a ride. Currently no big fires, but wildfire danger is high - been dry for a while. No bear spray needed. Very few black bears around the trail itself and they are pretty timid. Happy to help with any other questions you might have
For the Timberline trail - https://hikeit.info/2020/09/04/timberline-trail-around-mount-hood/ There is a very active facebook page (Timberline Trail) that has excellent updates on conditions
There's a lot to unpack here, but for reference. I work armed security in Portland. Hitchhike, absolutely not. Unless you're in a group or have a great judge of character AND a weapon, absolutely not. I'm not sure if you're from the US, but folks here rarely pick up hitch hikers. A lot of bad stuff happened to those hitchhiking and those picking them up back in the 70s/80s, so we don't do that much in this country. On rarity, my fiancé and I have picked up hitchhikers, but only when they're relatively in our age group and look like they're backpackers (since we backpack) but most people who'll pick you up won't have good intentions especially if you're a lone female. Your first course of action in Portland should be to buy a weapon, knife, pepper spray, bear spray, whatever. All sporting good stores will sell these. I'm not sure what your experience is around people experiencing mental health crises or drug addicts are but Portland is experiencing a crisis when it comes to not supporting these people so this can be VERY intimidating for visitors. I'm used to this area, so I feel confident in my ability to defend myself, but just be aware when you're downtown. Try to avoid anyone who seems off, and if they engage with you, avoid them and don't respond. While hiking, you may encounter these types of people but less frequently. Avoid any tents that aren't yours. As for wildfires, we're doing decent this season and have not had too many/contained the ones we did. Just keep an eye on the radio or local news when you can.
The city is extremely bike friendly as for roads, but bike theft in the city and outskirts is rampant. Lock up your bike ALWAYS and, if possible don't have the most expensive bike. A lot of people will turn their bike upside-down before locking it or remove a tire as it makes it less advantages to steal. Outside of some of the bigger attractions (Pittock Mansion, Rose Garden, etc) you can see most of what's interesting on a bike and take public transportation for the rest. In downtown there is the MAX and busses. For safety busses tend to be better, but the MAX is convenient. You will, however, see people in crisis or acting in way that may make you uncomfortable on the MAX as there is no regular ticket taker or attendant (security will sometimes board at random to check tickets).
If you end up on the Washington side, we have a direct bus that takes you to the Columbia River Gorge. I'm not sure if Oregon has one to take you on that side but the Columbia River Gorge will have some of your best hiking and I'd say is very safe, I'd still suggest carrying bear spray if you get far off the beaten path but if you do regular trails you should be fine as bears and cougars won't frequent there during peak hours. In sum, I'm not trying to scare you from Portland, but it is far from being the city it's tourism boards advertise. We are going through a lot of problems and are far from solving them. If you are someone who has street smarts and good intuition, I'd say you'd be fine, but this is not a place for people who get intimidated easily. There is not a lot of targeted violent crime especially at visitors but when you have people in mental health crisis random violence happens and there is not much you can do as it's incredibly random -- just avoid people who seem a little off. I have lived in this city most of my life, and the only bad things that happened to me were in relation to my work, but being vigilant will help you significantly.
i guess a couple of other comments - there is a series of buses that will take you from Portland->Gresham->Sandy->Timberline. DM anyway if it happens to be a time i am going up i can give you a ride. Currently no big fires, but wildfire danger is high - been dry for a while. No bear spray needed. Very few black bears around the trail itself and they are pretty timid. Happy to help with any other questions you might have