Before the highway tunnel, before the highway at all, travelers crossed between Central Maui and Lahaina the hard way: straight over the pali on a zigzag trail cut in the 1800s. The Lahaina Pali Trail is that road, still open, still brutal, and now decorated with wind turbines and some of the best high-angle ocean views on the island.
What you are signing up for
From either trailhead the math is similar: roughly 1,600 feet of climbing on rocky, ankle-rolling footing to the Kaheawa wind farm ridge, then (if crossing) down the other side. Point to point is about five miles; most hikers instead climb from one side to the windmills and return — call it four to five hours either way.
There is no shade. The leeward pali is dryland scrub and bare rock, and by mid-morning the slope becomes an oven — this trail generates rescue calls every summer from hikers who started at ten. Start at first light and be descending by nine, and it is a magnificent workout instead of an ordeal.
The trail itself is a piece of history: you are walking the 19th-century route between Lahaina and Wailuku, worn into the rock by horses, mail carriers and everyone else who had no other option. Stone steps and old paving survive in stretches — the pali's answer to the King's Highway.