The first time I biked in Portland, it was a balmy, cloudless day in July. I headed downtown along the Springwater Corridor Trail, right next to the river, past the Oaks Bottom Wildlife Refuge and far away from any cars.

It was awful.

The trail was crowded, and I was scared that if I tried to pass the throngs of riders in front of me, an oncoming rider would suddenly appear from around a corner, and I wouldn't be able to get out of the way in time. The number of cyclists between me and my family member, who was leading the way, kept piling up. Once we got off the Springwater, things got even worse. I had never ridden around cars before, and I was certain that at any moment I would topple to my doom.

Now, after years of bike commuting, I'm a much more confident rider. I can't imagine a day without getting on my bike. It's my sole means of transportation and what I do for fun on the weekends. But every time someone visits me from out of town and wobbles around the city behind me on a spare bike, I'm reminded how terrifying it can be, and how many things I don't even notice anymore—biking over railroad tracks, merging around buses in shared lanes, some dude in a bike jersey yelling at you for actually stopping at a stop sign—can feel like a crisis when each pedal stroke seems like embarking into the great unknown.

So we crowdsourced a list of common concerns that prevent beginner or otherwise tepid cyclists from enjoying their time in the saddle, and reached out to some local experts for advice—River City Bikes owner Dave Guettler, Tia Sherry of bicycle advocacy nonprofit the Street Trust, and Emily Guise of the grassroots organization Bike Loud PDX. Here's what we learned.

What can I do to motivate myself to ride when it's cold and raining, or make riding in the cold and rain less miserable?

Dave Guettler: If it's raining out, traffic gets horrible. Bike commuting is very predictable, pretty much no matter what time of the day you leave, whether it's a commuting hour or not. If it's raining, the possibility of heavy traffic goes up. One of my big anxieties regarding commuting is getting to work on time. Being able to accurately predict when I'm going to get there relieves some of my anxiety. Fenders on your bike is a big one. If you don't have fenders, you have water coming at you in all directions. Even if you get a little bit wet, you can stay warm with gloves and wearing a hat. Just wear things that will keep you warm, first and foremost. Then bring a backpack so you can take all that stuff off.

Emily Guise: Having a backup plan is good. A lot of times if it's raining really hard, I will bike to the MAX station and take that most of the way. I'm usually wearing a waterproof jacket, waterproof gloves and rain pants, but to be honest, I don't use them very much. I don't like wearing them, so I only wear them when it's raining really, really hard. A lot of the time what happens is, I get a little bit wet and then I dry off after like a half-hour when I get to my destination. It's usually not too bad.

What can I do to feel more safe riding on streets with cars?

Guettler: Route selection. You don't ride on the same roads as you drive, you ride along what parallels that busier road. [If you end up on a road where you don't feel safe,] first thing I would do would be to get off that road. I would find a neighborhood side street. Even if I have to go like a mile or two out of my way just to be safe, to me, that's a critical decision to make. I use a [handlebar side] mirror on all my bikes, I also use a bell on all my bikes. Cyclists have been known to run lights, pedestrians step out from behind cars, and bikes are quiet. If you ring your bell as you're approaching an intersection, I've had people stop in their tracks right before they step out from behind a truck.

Tia Sherry: If you didn't have quiet streets or neighborhood greenways available to you, consider adding a bus or a MAX ride to your bike trip. Use the bus or the MAX around those sections that are busiest. I will walk the route beforehand just so I can get a sense of the traffic. That typically will be busy with cars. Choose a time over the weekend that you can ride it with fewer cars. That way you can kind of build up your confidence.

What are some tips for buying a cost-efficient starter bike that doesn't totally suck?

Guettler: You want to get a bike that's as versatile as possible because you don't know what you're going to end up using it for. The bike industry has made a big improvement on lower-cost bikes starting in the $500 price range that are super-versatile—you can use them as touring bikes, you can put fenders on, you can add a rack. Pick out a bicycle that you can do as many things as possible on it, so you can adapt it to whatever you end up using it for.

Sherry: You can certainly get a starter commuter bike in the $300-to-$600 range. You can always build up. If you're starting out, ride the bike you have now. That way you can get acquainted with your route, your style and your schedule, and then you can start exploring other bikes.

Guise: This is where a bike shop that sells used bikes is going to really be your friend, especially the nonprofits like Bikes for Humanity, Community Cycling Center, Bike Farm. Those places are really great for budget and getting a bike that's not terrible. Usually what you need is a bike that fits you and a bike that feels comfortable when you're riding it, that's the most important thing. And probably one that you like looking at. If you're like, "I really love this bike, it looks so cool," you're also going to ride it more.

I don't have a big budget for gear. Other than a bike, what are the most essential things I need for bike commuting? How can I maximize my gear budget?

Guettler: A helmet is probably the first thing. Lights on your bike are super-important too, because you never know when you're going to be coming home later than you think or when it's going to be dark and rainy and you just want to be more visible. There's no argument against having bright lights on your bike and really good brakes. If you're going to be riding your bike 10 miles and you want to set yourself up for commuting every day, it would make sense to spend a little bit more and get stuff with Gore-Tex that's going to keep you warm and dry. If you're only riding 2 or 3 miles to work, you could put a garbage bag on.

Sherry: Invest in rain gear. Having rain gear that breathes and moves along with your body, that keeps the rain off your body can be costly but can also get you where you need to go dry and warm. I wear a pair of Gore-Tex rain boots, but if you're not able to have that, definitely you can get some rain covers. You can even just pick up a pair of wool socks that are larger than your normal foot size so you can slip that over your shoes. Wool breathes, it dries really quickly, and it keeps you really warm. So if you're not able to upgrade to rain boots or Gore-Tex shoe covers, wool socks, whether you buy them brand new or get them from your dad, you just slip them over your shoes, and you would be amazed at the difference that it makes. Warm feet means happy cyclists.

Guise: The most important thing to get is a good lock, absolutely a U-lock. Ones that are good enough to make your bike less attractive to steal are usually around $40 to $50. I would not skimp on that. I would also not skimp on getting good lights, front and rear. I think lights are just as, if not more, important than a helmet. Those two things are the most important to invest in, and I would pick up everything else as I go. I just wear regular clothes to ride in most of the time. I love Next Adventure's used-gear room for gloves or a rain jacket. Thrift stores are also great for boots that are water-resistant but won't break the bank.

What are some local resources or easy ways to learn more about my bike, or otherwise deal with feeling intimidated at bike shops or when dealing with bike mechanics?

Sherry: Choosing a bike shop is paramount to your happy bike life. Your bike shop could be the one that's conveniently located in your neighborhood or it could be one across town. When you go into a bike shop, you should feel welcomed, you should feel empowered, and you really need to feel like they are listening to you and what your needs are. If your current bike shop doesn't fit that, go elsewhere. Most bike shops have repair classes that are either free or inexpensive. Take those classes and don't be embarrassed when you have to take the classes again and again.

Guise: I have personally learned a lot from North Portland Bike Works. They have a women and trans wrench night. I built a wheel there and learned how to fix up a vintage bike and put new parts on it and stuff. There's Gracie's Wrench, she teaches you how to fix your bike and care for it. Gladys Bikes has classes about that too. Bike Farm is also wonderful. You fix up your bike there, it's drop-in, and there are folks there to help you. Community Cycling Center, they do classes as well, and Bike for Humanity, you can drop in and work on bikes that they've had donated and learn to fix bikes that way.

How do I learn cycling road rules and etiquette? Do I follow road rules of cars or pedestrians? Or is it a mix of both?

Guettler: Safety is the absolutely first consideration, frankly even more than absolutely following the letter of the law. If I do not feel safe in a particular situation or if I have to jump the curb and get up on the sidewalk, I do that. If I have to pull completely off the road and wait until traffic clears, I'm going to do that. [River City] leads a first-timer bike ride on Saturday mornings. I take people on the neighborhood greenways, just kind of talk about finding safe routes and developing safe riding habits, how to use your gears, how to use your brakes, very basic things.

Guise: Under Oregon law, people on bikes are classed as vehicles, the same as when you're driving a car. Until we can get that changed, it's best to ride in the street like you're a car. The Street Trust puts on rules-of-the-road workshops. Thomas, Coon, Newton & Frost, they represent Portland bicyclists, and they also have a legal guide for Oregon cyclists. Bikeportland.org has a lot of posts about legal things, so they're a good resource.

How do I manage to show up wherever I'm going not drenched in sweat and smelly?

Guettler: If you get to ride to your work in the morning, one thing you can do is shower right before you leave. Even if you have to climb over the West Hills or it's a hot day, even if you do work up a little bit of a sweat, it's not going to be a stinky sweat. And just take it easy, don't go hard. Give yourself a few extra minutes and go at a casual pace.

Sherry: Merino wool is a cyclist's best friend. It breathes, it dries quickly, it's odor- and stain-resistant. I wear merino wool as a base layer. I shower before I head out on my bike. Choose a route with little or no elevation. I like to arrive 10 minutes early to just cool off.

How do you deal with harassment, catcalling or just generally feeling vulnerable on your bike?

Sherry: It's hard. Do you stop and educate them or just pedal on and enjoy your fucking life? I choose the latter. I don't make eye contact, I don't acknowledge them. My commute is sacred, and I'm not going to let you into my space. Every time we get on our bikes, we really do put ourselves at risk. But is that enough to keep you away from the joys of riding a bike? Riding a bike, you are more in tune with the environment around you, your senses are heightened. You see everything, you smell everything, you can feel everything, and it's all our jobs to help each other overcome the barriers of riding a bike.