The Ultimate Maui Road Trip from Haleakala Through Upcountry Maui

The sugary sands of Maui are so enticing it can be hard to break away from the beach blanket. But for sweeping vistas, cooling breezes and charming old towns, you can’t beat an Upcountry Maui road trip. Here’s how to explore the island’s other charms, starting at the very top: the summit of Haleakala.

Kahului to Sunrise at Haleakala

Seeing the sunrise over Haleakala Crater is a breathtaking rite of passage. Get an early start, as it’s about a 90-minute winding drive from Kahului up to the summit of Haleakala, inside Haleakala National Park.

The summit itself is at 10,023 feet above sea level, an otherworldly landscape that feels more like Mars than Earth. Be sure to book a reservation for your vehicle in order to enter, which can be done up to two months in advance, and there will be a park entrance fee, as well.

This is a rugged landscape with no services, so fuel up the car and bring food, water and a refillable bottle, sunscreen and sturdy shoes. The summit has temperatures of at least 20 degrees below what it is at sea level, and at dawn it’s often windy and below freezing, so parkas and blankets are not overkill up here.

Take a Short Hike

There are more than 30 miles of hiking trails in the summit area, many of which are very challenging. For a light, quick hike near the Haleakala Visitor Center, try Pa Kaoao, a .4-mile round-trip excursion, or walk the beginning of Keoneheehee, also called Sliding Sands; the distance to the first overlook is a half-mile, round-trip.

Explore Farms in Kula

Begin your descent down the slopes of Haleakala and take State Highway 378 to Kula, a rustic and relaxed town where it feels like you can see all of Maui in the distance. Grab a cup of locally grown and roasted coffee at family-run Grandma’s Coffee House and then explore some of this beautiful farm country.

Alii Kula Lavender is a working farm and botanical garden with fragrant walking paths. Guided walking tours are available daily, and you can also order a gourmet picnic lunch (reserve the day before).

You’ve heard of goat yoga, but how about surfing goats? In lower Kula, Surfing Goat Dairy makes gourmet fresh and aged goat cheeses onsite. They offer behind-the-scenes tours of the farm, and the evening tour even involves milking the goats and tucking them in for the night. Awwww.

Get Artsy in Makawao

Country-chic Makawao was once a paniolo, or Hawaiian cowboy, town. Now it’s an artsy hot spot with galleries, like Hot Island Glass and Sherri Reeve Gallery and Gifts, and well-curated boutiques, such as Driftwood Maui.

Swing by the Hui Noeau Visual Arts Center, a public art studio that offers classes and hosts visiting artists and exhibitions inside a stately 1917 mansion. Its Gallery Shop is a great place to pick up locally made jewelry, glass, ceramics and other handcrafted gifts.

Surf Chic Shopping and Dining in Paia

Continue heading down Baldwin Avenue to Paia, where island chic rules the day. The town used to be a hippie haven — and has a great health-conscious grocery and deli called Mana Foods. These days, it’s added on a layer of hip, with alluring boutiques offering stylish swimwear (try Lilikoi Paia Maui), gifts and clothing.

Finish up the day at Mama’s Fish House on the beach on Maui’s North Shore. The restaurant serves fish so fresh that it’s been caught that day by fishers who bring their catch — opakapaka, uku, papio — directly to the restaurant.

As a result, the menu reads in a uniquely personal way, “Ahi Caught by Mike Fisher trolling through the Alenuihaha Channel,” for example. The restaurant is fairly upscale, so plan to wear informal resortwear and make a reservation well in advance.

After dessert, it’s just a short 20-minute drive back to Kahului on Highway 36.