I actually raced cross country skiing in high school too, but while I enjoyed it, and was pretty good at it (top 20-25 in the state in skating technique, I forget exactly, and I believe 11th in classical, skiing in a league that sent at least one guy I knew to the Olympics), I didn’t stick with it in college - I might have been able to hang as a walk-on in college, but my school’s program was REALLY strong, and this corresponded in the period of my life where I started to get really serious about guitar and writing music.
I can count the number of times I’ve ridden without a helmet on one hand in the last five years. Two of those were occasions where I just didn’t have access to one - picking my bike up from the shop after work, a day earlier than it was expected to be ready, and going straight from work to get there in time so I couldn’t stop to grab my helmet - and maybe on one occasion I did a quick spin around my block to test out something on my bike I’d been dialing in. I REALLY don’t like riding without one, though - I feel naked without one, I don’t trust drivers, and even a person who trips while walking can hit their head hard enough to give themselves a consussion. Even a slow rider going about 10mph will hit exponentially harder than that, and while I do occasionally just cruise, my not-really-killing-it-but-still-giving-it-some-effort-on-a-straightaway-with-no-headwind pace is low-mid 20s, so I’m not chancing it.
I’ve never done any bike racing (other than racing buddies when we’re out for a ride), but my brother used to (just started back up again, after five years off, and went from barely holding on as a Cat 2 rider after upgrading to being a solid middle of the pack rider while just training for fun for five years, dude’s a monster) and I’ve watched him in a bunch of crits, and I think they look fun - it’s kind of like chess, at 25mph. I’m definitely a proverbial Strava Cat 6 hero, though - picking up KOMs in the Boston area is tough since there are SO many exceptional riders up here, but when I’m going for it I’m usually putting up pretty respectable times on segment leaderboards.
You wouldn’t believe bike technology today. While there’s some overlap, with two rings in the front and 11 cogs in the cassette I have 22 gear combinations, with shifters integraded into the brakes so I can shift just by flicking them sideways without taking my hands off the bars, and carefully indexed so shifting is razor-sharp. I actually havent weighed my Tarmac since swapping the stock wheels for Enves, but it’s probably right around 17lbs for a 58, which if you’re not used to it is almost laughably light - carbon was a game changer.
If what you loved about skiing was being out in the wilderness and snow, have you tried snowshoing? I think that’s a better way to get way off the beaten path, since you have much more control in the backcountry, both going up AND down hills.