I'm a volunteer ski patroller on the weekends, so I get a free family pass. My son and I go up every Saturday, I pack my lunch and bring a thermos of tea and buy a pepsi and the paper at a quick stop on the way up. I give my son $5 walking-around money, he and his buddies maintain a locker full of ramen which they "cook up" by bumming hot water from the cafeteria line. Since we arrive very early, the kids help the cafeteria workers set up the lodge tables and they get free breakfast. I spring for drinks candy and doughnuts on the way home, another $10, tops. My ski day costs me less than $20, total. I get deals on gear by being on the Patrol, usually half or less of retail, I go to the summer sale at Burton and get stuff insanely cheap. I have bought good poles for $2 at the Salvation Army, they charge $5 for boots and skis. I actually bought boots there once, which I used for 2 seasons. I outfitted my kid some years ago for $40 total at a fall ski swap. Before I was on the Patrol, I bought season passes el cheapo during the summer.
Yesterday me and my son with 2 buddies took a ski trip up to Jay Peak. I got a free comp pass, my son got one for $20 by flashing his Smuggs pass, one buddy had a season pass to Sugarbush, so he flashed that and got a $20 pass, the other paid $30 Vermonter teenage price. We packed food, but bought a few food items. The total outlay for the 4 of us was less than $100 for a great day. We maxed the lifts out with first and last chairs.
I've never skied Stowe, even though I live nearby, because they won't give a break on a pass. Likewise, I've never skied Killington. I don't think my son could maintain a ramen locker at either place. I've skied Mad River because once a year they do lift tickets for the 1948 price ($3.50), if you dress up in old ski clothes.
Likewise, I golf on the cheap, no country clubs for me. If it's $30 or more, I don't tee it up. I play with found balls, I paid $100 for homemade clubs.