Let's be honest here; when we talk about winter cycling there are just a handful of us willing to brave the elements. I head out in the worst of winter storms to downhill or cross country ski, but find myself wincing at the thought of snow flurries on a bike. Let me walk you through a host of options for staying "cycling fit" during the winter; the reality is a good mix of all of the options is your best bet to staying warm, staying fit and having fun.
The obvious option is fat biking in the snow. The local bike shops have plenty of options for rentals or to purchase your perfect bike. The trick is always finding the right conditions (plunging through 6 inches of fresh snow on a bike is ridiculously hard!) Most people head up to the Wanoga Snow Play Area which has groomed trails just for fat bikes. Check out Central Oregon Trail Alliance for all the fat biking fun details.
If you are more into gravel cycling, you can often watch the weather and find perfect conditions to ride. But along with that comes choosing the perfect route. I'm always looking for flat routes just so that I can keep my body temperature about the same for the whole ride. Nothing makes me colder than climbing 1,000 feet and then descending; I am guaranteed to have a teeth-chattering experience on the way down. My body temp cools off too fast and the sweat just makes me cold.
I also search for routes that have good punch-out options or are much closer to town. If I need to call a friend because the weather went south, I want a warm place to hang out and wait. Or I like smaller loops that give me a constant "return to the barn" option.
For sneaking in the winter miles, I like to ride Dirty Freehub's Coffee Run route which allows me to spin from Bend to Sisters, warm up with a good cup of coffee and then spin back. I also like Dirty Freehub's Westside Tour because this one has a million different bailout points. For days when the weather is looking really dicey, I will stay in Bend and use Dirty Freehub's Townie route. People who have lived in Bend a million years will tell you the route has paths that they didn't even know existed!
If I don't mind a bit of a drive, Dirty Freehub's Donnybrook route north of Madras has roads that typically stay dry and fast in the winter. A big chunk of this is paved with this 54-mile loop offering up plenty of climbing to keep you in tip-top form. And for a longer drive, I would consider Dirty Freehub's Macks Canyon route out of Dufur, which can be "hot diggity" warm on a sunny day because you are low in elevation and tucked nicely away from the wind. It's also 34 miles with less than 1,000 feet of climbing.
For you mountain bikers, who doesn't love to head to Maston on a warm sunny winter day? The biggest trick is to make sure you are not riding trails when they are muddy, which is often the case. (You destroy the trails if they are muddy!) For the latest trail conditions, check out Bend Trails.
You can also just admit defeat and buy Nordic skis. There's no better sport on the planet to crank up your lung capacity than skate skiing. Both Mt Bachelor and Meissner Nordic offer up lung-sucking fun.
Or you can skip going outside altogether and just train indoors.
My recommendation is to crank out hard workouts that are about an hour, using one of the apps like Zwift or take a class with a drill-sergeant coach. They both can help work on important bike skills like cadence and power surges. Check out Bowen Sports Performance if you want to try an indoor cycling class full of chatty cyclists.
My final tidbit is to create a spring goal, like the Gorge Gravel Grinder in Dufur, Oregon. Nothing pushes me out the door on winter days like a looming 53-mile bike ride (the "small" event) on my calendar in April. (They also have 67- and 93-mile options!)