9 Best Sights in Upcountry, Maui

This is one of the few places on Earth can you drive (or bike) from sea level to 10,023 feet in only 38 miles. What's more, in that ascent to summit of the Haleakala volcano, you'll journey from the lush, tropical island landscape to the stark, moonlike basin of the volcano's enormous, otherworldly crater.

Several trails take in these varied landscapes, including the Keoneeheehee (Sliding Sands) Trail, a hike with out-and-back segments to overlooks and down into the crater; if you're truly fit and ambitious, you can even follow it all the way across the crater floor. Hikers and those camping at the tent-only Hosmer Grove Campground (reservations required) should check in at the Park Headquarters Visitor Center, near the Summit District entrance. This is also a good place to learn about the volcano's history and pick up trail maps at the gift shop. You'll also find the Haleakala Visitor Center at the crater's summit.

If you plan to head to the summit before 7 am, you must make sunrise reservations, which you can do up to 60 days before your visit. (Make these and campground reservations at  recreation.gov). Although a few last-minute sunrise-viewing tickets are released online two days out, they can be difficult to secure. Alternatively, consider visiting for sunset. Reservations aren't required and, on most days, the views are as stunning as those during sunrise.

Regardless of when you head up Haleakala, check ahead for the latest weather conditions. Extreme gusty winds, heavy rain, and even snow in winter are not uncommon. Because of the high altitude, the mountaintop temperature is often as much as 30°F cooler than that at sea level, so bring a jacket. In addition, the air is thin at 10,000 feet, so don't be surprised if you feel breathless while walking around the summit. Take it easy, and drink lots of water. Anyone scuba diving within the last 24 hours should not make the trip up Haleakala.

Note that entrance tickets are valid for three days. It's a good idea to hold onto your receipt in case you want to visit the Summit District on more than one day, or you also plan to visit the park's Kipahulu District in East Maui as part of a drive along the Hana Highway.

Most of Maui's produce is grown Upcountry, which is why everything is fresh at this outdoor market located next to Long's in the Kulamalu Town Center. Every Saturday from 7 to 11 am, vendors offer fruits, vegetables, flowers, jellies, bread, plus unique finds like venison, kimchi, and fresh-caught fish. Prepared food offerings reflect the island's cultural melting pot, and there's an excellent selection of vegan and raw food. Go early, as nearly everything sells out.

The view is spectacular from this lavender farm established by master horticulturist and visionary Alii Chang. You can explore the property on your own or reserve a spot for the 30–40 minute tour that winds through paths of therapeutic lavender varieties, protea, and succulents. The gift shop has many locally made lavender products, such as honey, moisturizing lotions, and scone mixes.

More of a friendly gesture than a town, this tiny outpost is the last bit of civilization before Kula Highway becomes a winding back road. A coffee tree pushes through the sunny deck at Grandma's Coffee House, the morning watering hole for Maui's paniolo (cowboys) who work at Ulupalakua or Kaupo Ranch. Keokea Gallery next door sells cool, quirky artwork. And two tiny stores—Fong's and Ching's—are testament to the Chinese immigrants who settled the area in the late 19th century.  The only restroom for miles is in the public park, and the view makes stretching your legs worth it.

This picturesque garden has assimilated itself naturally into its precipitous 8-acre habitat. More than 2,500 plants and trees fill the enchanted garden, including native koa (prized by woodworkers) and kukui (the state tree, a symbol of enlightenment). A flowing stream feeds into a koi pond, where nene and ducks meander, and a paved, stroller- and wheelchair-friendly pathway winds through the grounds. The carved tiki exhibit, aviary, and Jackson chameleon exhibit entertain the keiki (children).

Situated at around 8,800 feet, the Leleiwi Overlook provides your first breathtaking glimpse of Haleakala Crater. The small hills scattered across the basin are ancient Hawaiian cinder cones, or puu. If you visit in the late afternoon, you might witness a rare and magical sight: your shadow cast on the clouds, surrounded by a rainbow halo—a phenomenon known as the Brocken Specter. However, don’t linger too long in anticipation, as this mesmerizing occurrence is far from guaranteed and happens only under perfect conditions.

Pineapple exudes tropical happiness, and it just so happens Maui has the only tour of a working pineapple plantation in the United States. You'll join a worker on a stroll through the sunny fields and hear all about the especially sweet Maui Gold pineapples, sampling the fruit in various stages of maturity along the way. The best part? Everyone gets a free pineapple at the end! For an extra fee, you can also tour the nearby Haliimaile Distilling Company to learn about its operations and taste Pau Maui Vodka, the world's only pineapple vodka. Time things right, and you'll be able to enjoy lunch or dinner at the renowned Haliimaile General Store just across the street from the distillery.

The highest point on Maui is this 10,023-foot summit, where a glass-enclosed lookout provides a 360-degree view. The building is open 24 hours daily, and many visitors gather to view the sunrise. Bring jackets, warm layers, hats, and blankets to stay warm on the cold and windy summit. On a clear day, you can see the islands of Molokai, Lanai, Kahoolawe, and Hawaii; on a crystal clear day, you can even spot Oahu glimmering in the distance.

It takes goats to make goat cheese, and they've got plenty of both at this 42-acre farm. The owners make more than two dozen kinds of goat cheese, from the plain, creamy "Udderly Delicious" to more exotic varieties that include tropical ingredients; all are available in the dairy store, along with gift baskets and even goat-milk soaps. Thirty-minute walking tours of the dairy and farm are held throughout the day, or you can opt for the educational and fun Evening Chores and Milking Tour. Online tour reservations are recommended.