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(thanks to Wikipedia for the detail).
Catching a sunrise on Haleakala is one of the most breath-taking and beautiful sights one can imagine.
Head towards Kahului EXTREMELY EARLY in the morning (~3-4am). Take 37 East and turn left on 377. Head east / south for 6 miles then turn left on 378. Proceed up the volcano ("mountain") via the zig zag road. You're probably going to get stuck behind slow drivers or a bus. This road is nearly 19 miles and very slow. Did I mention to leave early?... You're driving from sea level to 10k+ ft elevation. It'll take 2-3 hours so plan to leave such that you will arrive sufficiently before sunrise.
Continue along 378 all the way to the peak and park in the lot. Then follow the signs for the Pa Ka'oao trail to the summit (adjacent to the visitor center). A flashlight or phone light is necessary so you can see the trail and not trip/fall and become injured.
At the summit you'll have to deviate off the tail... perhaps this is "discouraged" by the signs, but virtually everyone does it. Follow the crowd and you should be fine.
Due to the elevation the temps are below freezing. Beautiful looking ice crystals form on the ground from the moisture in the air. Even though you're in Hawaii, the summit - especially during "winter" - is very cold. Bring LOTS of layers to keep warm. A sweat shirt, fleece, or rain jack by themselves are not sufficient. I know you're in Hawaii, but really, this area is darn cold. Layer up.
By the way, there is NO ROAD WHICH CONNECTS WAILEA TO 37 AS A SHORT CUT. IF YOU SEE A ROAD ON GOOGLE MAPS, IT IS PRIVATE PROPERTY AND BLOCKED OFF. THERE IS NO SHORT CUT. ONE MUST TAKE THE "LONG WAY" TOWARDS THE KAHULUI.
I recommend to go the first or second day after you arrive to Maui before adjusting to the time zone change. It's easier to wake up very early (assuming you're traveling east -> west). Also, you'll need to pay for a park pass which is active for a few days if you want to visit around the Pipiwai Trail / Seven Sacred Pools on the eastern side of the island.
One final thought - the weather may not cooperate and you may need to return on the following day(s). I was lucky and had a beautiful sunrise on the first attempt. Another person there mentioned he had to attend 3 straight days. But the sunrise is absolutely work the effort.