Thompson Road
Here’s the thing about traveling on an island: there are only so many places to go. Every road eventually leads to a mountaintop or a beach, and seeing as Maui is smaller than the city of Jacksonville, Florida, you can’t help but wonder—how many secret streets can there be on a rock that’s surrounded by ocean?
A lot, actually. Some streets on Maui—like the Road to Hana—are sights unto themselves, whereas others, like Lahaina’s famous Front Street, are a staple of any visit. On this list, we’ve highlighted some lesser-known stretches that aren’t as crowded as those that make the brochures, yet still offer swoon-worthy scenery, shopping, history, and lots of room to explore.
If you find yourself on Makena Road, you’re probably on an adventure. After all, though much of Maui’s southern shoreline has been systematically developed, Makena is where the southern coast is still a bit raw. It’s a place where strings of white sand beaches help thin the sun-tanning crowds, and crystalline coves full of turtles and fish invite a morning snorkel. Surfers hike to hidden breaks, there’s an ancient pathway of kings, and Maui’s only officially nude beach is a short walk off of the road.
If staying in Wailea, spend half a day driving to the end of Makena Road. Along the way, you’ll pass little-known beaches like Palauea, or “White Rock,” as you head toward Makena Landing and the historic Keawala‘i Church. Just past Makena State Park (or “Big Beach”) the road becomes single lane; look for the trail to “Secret Beach” that’s actually a hole in the wall. Eventually the road is so close to the coast that waves crash up on the pavement, which eventually crosses the island’s last lava flow from 1793.
With the exception of visiting ‘Iao Valley and the Bailey House Museum, not too many visitors to Maui ever find themselves in Wailuku. As the County seat and site of the island’s government offices and buildings, Wailuku has a concrete, almost urban, atmosphere.
That is, until, you get to Market Street—the main vein of an aging town experiencing a funky rebirth. Health food bars and coffee shops have helped the street perk up, and chic boutiques and new-age spas add cosmopolitan flare. On the first Friday of each month, the street becomes a pedestrian mall full of vendors and live entertainment, with the architectural pièce de résistance being ‘Iao Theater—a Spanish Mission style building and oldest theater in Hawaii.
A mile above Makawao’s only intersection, where pastures filled with grazing horses give way to Eucalyptus, Olinda Road is a serpentine climb through Maui’s misty uplands. Drive by Po‘okela Church—one of the oldest churches in Hawaii—before passing the Oskie Rice Roping Arena and site of the Makawao Rodeo. From here, four steep miles of two-lane asphalt lead to the Waihou Spring Trail, where a narrow walking track laden with pine needles leads to a hidden gorge.
Unless you’re a windsurfer, local, or fisherman, you’ve probably never heard of this road set two miles west of Pai‘a. A single-lane, sand-strewn road that runs behind Kahului Airport, Stable Road offers access points to a cluster of hidden beaches. Pack an umbrella, a towel, a book, and find your own patch of sand, and sit and watch the planes take off as they roar above the waves. Afternoons can be wind-whipped and gusty, so arrive early for calm conditions on the narrow, thin stretch of beach.
Tucked away in a quiet corner of rural Keokea, Thompson Road is the best spot on Maui for a morning jog or stroll. Flanked by pastures and lava rock walls, the single lane road offers views that stretch from Haleakala’s summit to the glitzy, sandy, Wailea shoreline nearly 3,000 feet below. Begin with a coffee from Grandma’s Coffee House, and continue with a leisurely, mile-long stroll past fleece-wearing locals who smile and wave while out for a walk with the dogs.
