High winds are both the most awesome and worst thing you can bike in.
Strong headwind is a soul crushing, face numbing, fun destroying, anger inducing pile of crap that you have to dig deep and learn to put up with.
Strong tailwind behind you though? It's like freebasing 30 year old oak aged, triple distilled unicorn blood. You will see colours blur and stream by you until you approach superluminal speeds, finally slipping free of the surly bonds of earth and cycling forward to touch the face of God.
The following things have helped me a lot biking long distances into the wind on snowy winters:
- High seat, low handlebars
- Narrow handlebars
- Keeping your head very low to your handlebars
- Keeping your elbows tucked in, close to your body
- Wearing snug fitting clothing that doesn't flap around
- Realizing that it's going to take about 30% longer to get where you're going if you have a hard headwind.
- Realizing that you will be twice as hungry when you get there.
I don't know if trailers are like panniers in high winds . . . but panniers can catch a good amount of wind and knock you pretty hard from left to right, so you have to stay very alert.