Since I moved to the NW a couple of years ago I've been considering a multi-event weekend. You could climb Beacon Rock in the early afternoon, windsurf in the late afternoon, then do a road ride from Hood River to Timberline, climb Hood, and finally ski down. Why? Because you can.
So Friday 7/18 after not planning anything fun for the weekend, I caught a ride to H. River with a couple of friends and started the adventure. They dropped me off at the H. River Event site (elevation 100) and by 8pm I was starting the journey up Hwy 35 with my MP3 player blasting. It was amazing to watch the sun set slowly on Hood.
Just after midnight I finished the 49 mile 5,000+ ft climb to Timberline. While I had planned on climbing solo (since I couldn't find anyone to join me at H. River), late Friday afternoon a couple of friends decided to join me for the climb. Since it was their first climbing experience the South was perfect, and I was slower than normal after the ride.
They didn't get to Timberline to 1am which put us on the trail about 1:30am. It was hot! I decided to hike in a t-shirt and running shoes and carry my tele-boots and skis on my pack. I ended up hiking like that all the way to the hogs-back. At the H. Back we decided the rope wasn't necessary and then blazed to the summit by around 6am. The B-shrund was easy, but may collapse one of these warm days. We hung out on the summit for 45 minutes.
The frozen sun cups would have been impossible to ski down from the Hogs Back so I walked down a 800 ft before doing some "battle" skiing back to Palmer for a final groomer to Timberline. I arrived back at Timberline at 9am, 13 hours after I started.
Now you have another option some day if you're really bored and the South slog alone doesn't sound that appealing.
11,0000 ft in 10 hours. This satisfies one of the previous post requirements that you start all climbs at/near sea-level.