4.9
(6)
791
riders
47
rides
Road cycling around Haliimaile, located at an elevation of approximately 1,106 feet (337 meters) in Maui's Upcountry, offers varied terrain. The region features agricultural lands, historically pineapple fields, transitioning to lush, forested slopes leading up to Haleakalā. Cyclists can access routes with significant elevation changes, from rolling hills to challenging mountain ascents through volcanic landscapes.
Last updated: July 2, 2026
17
riders
72.8km
03:50
1,400m
1,400m
This difficult 45.2-mile road cycling loop from Pukalani to the Windmills in Kula Forest Reserve offers challenging climbs and spectacular v
5.0
(2)
323
riders
93.2km
05:43
2,570m
2,570m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

Sign up for free
55
riders
31.9km
01:45
580m
580m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
32
riders
116km
06:21
2,280m
2,280m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
18
riders
57.1km
03:03
910m
910m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Start today with a free account
Your next adventure awaits.
Login or Signup
Popular around Haliimaile
A very nice trail; you can do it as a loop or a little further. There's a picnic area there.
0
0
Be sure to bring swimming shoes, there is a ford on the way that you have to wade through,
0
0
Be sure to bring swimming shoes, there is a ford on the way that you have to wade through,
0
0
Beautiful mountain ride through different zones of climate and vegetation. Perfect asphalt. Considerate drivers. 15 dollars entrance fee to the national park, even for cyclists.
0
0
Here you have a great view into the volcano funnel. It's also a great position to watch sunset.
0
0
This is a wonderful drive on an excellent road up to 3060 m altitude. We drove partly through clouds and short before the summit it cleared up and we got awarded with an outstanding view around the island.
0
0
Twin Falls Park is home to the first waterfalls and pools that are easiest to access on the Road to Hana. The picture-perfect falls are ideal for cooling off on a warm day, and the short jog around the park is a great way to take a break if you are on an extended sightseeing adventure in the car. You will likely encounter fewer people after the first falls, especially early in the day. Non-Hawaii residents have a parking fee of $10, and it is important to note that access is limited to Maui residents only on the first Saturday of each month, including walk-in visitors.
0
0
North Pāʻia Beach, also known as Pāʻia Secret Beach, is a small, unmarked, coarse sandy beach only accessible by foot. It is a very quiet place with a come-as-you-are vibe if you are looking for a spot in a secluded location to relax and read a book.
0
0
Road cycling around Haliimaile offers a diverse range of terrain. You'll find agricultural lands, historically pineapple fields, transitioning to lush, forested slopes leading up to Haleakalā. Routes feature significant elevation changes, from rolling hills to challenging mountain ascents through volcanic landscapes and lush ranch land. The Upcountry climate is generally cooler than coastal areas, providing a comfortable riding environment.
Yes, while Haliimaile is known for challenging climbs, there are also routes suitable for beginners. The region offers a network with options for different ability levels, including moderate loops. For example, the North Pāʻia Beach – Rodeo General Store loop from Kauhikoa is a moderate 19.8-mile path that offers a ride towards the coast.
Haliimaile is an excellent base for challenging road cycling. One of the most iconic is the ascent up Haleakalā, often referred to as the 'Ride to the Sun,' which climbs over 10,000 feet. A challenging route in the area is the Pukalani to the Windmills loop —Kula Forest Reserve, a difficult 45.2-mile trail with over 4,500 feet of elevation gain. Another is the Haleakalā National Park – Crater Road loop from Pukalani, a 32.5-mile difficult trail leading through the National Park.
Cyclists can enjoy dramatic shifts in scenery, from tropical vegetation at lower elevations to volcanic landscapes near the summit of Haleakalā. Routes also pass through lush ranch land and agricultural areas, offering views of the island's diverse ecosystems. You might encounter natural features like First Falls or experience the challenging Haleakala Climb itself.
Yes, Haliimaile and its surrounding Upcountry region offer several points of interest. You can explore the charming plantation town heritage of Haliimaile, visit the Haliʻimaile General Store for local flavors, or take a tour at the Haliʻimaile Distillery. The Maui Pineapple Tour is also located in Haliimaile. For natural landmarks, the Haleakala Climb is a major attraction, and you might pass by First Falls on some routes.
The Upcountry region, where Haliimaile is located, generally offers a cooler climate than coastal areas, making it comfortable for cycling year-round. However, for the most pleasant conditions, consider cycling during the drier months. Always check local weather forecasts, especially if planning a high-elevation ride like Haleakalā, as conditions can change rapidly.
Yes, many of the road cycling routes around Haliimaile are designed as loops, allowing you to start and end in the same location. Examples include the Pukalani to the Windmills loop —Kula Forest Reserve and the Haleakalā National Park – Crater Road loop from Pukalani, both offering extensive circular rides.
While specific parking areas for each trailhead are not detailed, the proximity to towns like Paia and Makawao means you can often find public parking options. Many routes start from or pass through these towns, which typically offer facilities for visitors. Always check local signage for parking regulations.
Generally, no special permits are required for road cycling on public roads around Haliimaile. However, if your route takes you into Haleakalā National Park, there may be entrance fees or specific regulations for cyclists, especially for summit access. It's always advisable to check the National Park Service website for the latest requirements before your ride.
The road cycling routes in Haliimaile are highly rated by the komoot community, with an average score of 4.9 stars from several reviews. Cyclists often praise the varied terrain, from challenging ascents to scenic loops, and the dramatic shifts in scenery from agricultural lands to volcanic landscapes. The cooler Upcountry climate is also frequently appreciated.
Yes, the Upcountry region is well-equipped with amenities for cyclists. Towns like Paia and Makawao, which are often part of or easily accessible from Haliimaile routes, offer a variety of cafes and restaurants where you can refuel. Haliimaile itself has the Haliʻimaile General Store, known for its local flavors.
There are over 45 road cycling routes available around Haliimaile, catering to various skill levels. This includes 8 easy routes, 22 moderate routes, and 16 difficult routes, ensuring options for every type of road cyclist.


Browse the best Road cycling routes in other regions.