My background is that I've cycled for as long as I can remember but for many years they were all mainly short trips as I never plucked up the courage to go out and do the long rides I daydreamed about. Then a couple of things happened which changed that: Firstly I had a car dealer ask me why I even needed a car as I was driving such short distances
(6 miles each week day), then I spent a day sailing and realised how unfit I really was. A cheap bike was purchased (so as not to risk the best bike) and I started cycling to work.
Rides to work led to more pleasure-trips, which led to wanting to go further afield, which led to actually doing those rides I had daydreamed about before moving on to more adventurous ones still.
Initially what I got out of cycling was getting fit, losing weight and saving the cost of fuel and parking. What I get now is that cycling makes most trips into an adventure in a way that driving has long since ceased to do and I get a real buzz from riding big distances or on challenging routes. I find I enjoy the scenery more from the bike too - the views from the hill tops seem far more epic when you've had to work to get there and I've been to places that I'd probably never have seen at all if I hadn't been on the bike.
Although my preference is fair-weather riding I do ride through the winter, mainly because I start to feel stir crazy if I haven't been on the bike for a few days. The winter just gone was difficult and I got wet a fair few times, but still enjoyed the rides.
As with any outdoor activity in winter, the secret is layers of clothing so that you can adjust it to suit. For example, you're likely to want to be well layered up at the start of a ride, but once you've got a couple of miles done you'll start to warm up properly and will want to shed a layer or two. I find a Buff really useful. Worn under the crash hat it keeps in the warmth in winter but also wicks away sweat in summer to keep me from overheating.
Your bike will need to be looked after more in winter. The dirt, grit and salt off the roads is not good for drivetrains and will also wear brakes faster than usual.