Your best bet for being on a highway that isn't "steep and winding" is usually an Interstate. Even though it's not the shortest distance, I'd recommend I-70 west to Clifton (just before reaching Grand Junction), then follow the signs ("to Montrose) to cut over to US 50 and drive south (although it'll say US 50 West) to Montrose.
I-70 doesn't have any "scary" terrain, will be one of the first highways to be plowed if there is snow, and has a higher speed limit than the more southerly US 285 to US 50 route.
However, it is wise to check road conditions before making your final decision. Look at conditions on Monarch Pass (the southern route) vs. Vail Pass (the I-70/northern route) and let that help you decide which route to take the day you are traveling.