I rode to the Squaw Peak lookout today for my afternoon ride. I've never been on that ride before--last year I made it 1/2 a mile up the road before I turned around. I really wanted to do it this year. I figured after riding the Alpine Loop last week it would be doable--but not easy. That was accurate.
The Squaw Peak lookout is 2200 feet above the valley floor and you're doing most of that in a little under 5 miles. The whole ride is 20 miles round trip from my house. I burned about the same number of calories as I do riding to the end of South Fork and that ride is seven miles longer (but 500 feet less elevation gain). For the most part, I'd put it somewhere between riding South Fork and riding to Sundance, but the last 1/2 mile is a real killer. I took a few pictures.