Maui, Hawaii
71 miles | 9,800 ft elevation
The ride up Haleakala is a 36-mile climb (72 miles roundtrip with an average of 5% grade), starting at sea level and reaching 10,000 feet at the summit. The terrain and temperature changes dramatically as you reach various levels of elevation, and it’s pure climbing all the way up.
Starting out in the town of Paia, it will mostly likely be warm and humid, but before you know it, you will be high above the trees and heading towards the clouds. At about the 13 mile mark, before you start up Crater Road, be sure to stop at Kula Market Place to refuel and use the restroom (there are no other services until you reach the top). 
As you ride the countless switchbacks, the terrain will go from green farmland to brown lava rock, and soon you will be high above the clouds. It is not uncommon to get wet as you make your way through the clouds (so be sure to pack layers!), but you may get lucky and remain dry on your way up.
Once you reach the top, there will be a large parking lot, but keep going 1 more mile to the summit for the ultimate 360 view and photo op under the elevation marker. After a quick break, layer up for the long descent back to town (trust me, you will want long finger gloves and a jacket). 
The trip back is unreal, as you coast all the way back down for hours. It was truly unlike anything I’ve experienced on the bike before (It was literally a 2-hour descent!)
Hotel Recommendation
Maui Kaanapali Villas – This hotel feels more like an apartment/condo complex with spacious rooms (including full kitchens and living/dining areas), plenty of parking and access to the beach. It is a very quiet property and a perfect place to call home for a few days. It is a short drive to Whalers Village, where there are many restaurants (my favorite was Monkeypod) and shopping. It is also within walking distance to The Westin resort, which also has a few restaurant options.
There are many places to stay throughout the island, some more remote than others. Do your research and find what is best for you and your budget.

Haleakala is a National Park, so you will need to pay a park entrance fee (even if entering via bike). Be sure to review the official National Park website for the latest information.
Check the weather forecast for the top of Haleakala and bring layers! You may get damp riding through the clouds and the descent down will be cold for the first few miles.
There can be quite a bit of traffic on Maui (most roads are only two-lane roads), so be prepared for it to take a while to drive to various locations on the island.
In general, there are not many places to stop for food while riding, so be sure to pack enough food and water.
If you don’t want to fly with your bike, you can rent a road bike from Maui Cyclery. Reserve your bike online (you can also add a bike rack to your order if you plan on renting for multiple days and need to transport the bike), and then give them a call to confirm your reservation and ask them any questions you may have. The guys in the shop are super helpful, giving route and rest stop recommendations, and they will even put your pedals on for you upon pick up. If you plan on starting your rides early, pick up your bike the day before as they don’t open until late morning.
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