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Our Guide to Hawaii’s Most Beautiful Island

Hawaii's most beautiful island is probably one you've never heard of. Located just east of Oahu, Molokai offers an untamed look at the state’s natural charms, including pristine beaches, clear water, and, best of all, uninterrupted solitude. Read our guide to the place, then go book a trip. (Dylan Silver)
Molokai, Hawaii

Hawaii's most beautiful island is probably one you've never heard of. Located just east of Oahu, Molokai offers an untamed look at the state’s natural charms, including pristine beaches, clear water, and, best of all, uninterrupted solitude. Read our guide to the place, then go book a trip.

There aren’t any stoplights on Molokai. There aren’t freeways or resorts either. There’s no fast food, no Walmart, no ABC stores. Most of the roads don’t have lines. Most of the buildings are about half as tall as the average palm tree. Fewer than 7,500 people live here, and fewer people visit Molokai in a year than go to Maui in a single month. This makes it easy to find quiet beaches, secret trails, and undisturbed forests. Halawa Bay, on the island’s east shore, exemplifies the empty beauty of the place.

OutsideOnline Empty Hawaii Molokai silver cove beach no fast food population palm tree
(Dylan Silver)

Molokai is often called the most Hawaiian of all the islands. The locals have resisted major resort developments, agricultural operations by Monsanto, and efforts to build wind farms. This has preserved the Mana, or spirit, of the island, says Anakala (Uncle) Pilipo Sartorio, the oldest resident of the remote Halawa Valley. Sartorio— whose ancestry runs deep in the island’s history—teaches visitors about ancient Hawaii. Shown here, he greets his son in the traditional manner.

OutsideOnline silver Molokai spirit mana Halawa Valley locals no resort Anakala Sartorio
(Dylan Silver)

Moaula is just one of many waterfalls on Molokai, but it’s likely the most accessible. If you want to visit the falls, you must arrange a trek through one of the few tourism outlets. Though it can be costly, the semi-rugged hike winds through Halawa Valley, where the stone walls and ancient taro terraces offer a window into Molokai’s oldest settlement. The cool pool at the bottom of the falls offers a nice reprieve after your jaunt.

OutsideOnline silver Molokai Moaula waterfall pool Halawa Valley accessible hike
(Dylan Silver)

For the most part, the island’s North Shore is steep. Very steep. These are the world’s largest sea cliffs, dropping more than 3,000 feet to an uninhabited shoreline. There are few ways to get good views of the escarpments, though. Aircraft have the best shot—if it’s not too windy to fly. The only other options are to take a boat or cover the breakneck Kalaupapa Trail on foot or muleback.

OutsideOnline Empty Hawaii North Shore steep sea cliffs uninhabited shoreline escarpments Kalaupapa Trail foot mule
(Dylan Silver)

The Kalaupapa Peninsula is Molokai’s most famous landmark. Though the scenery is remarkable, the former leper colony is what draws most visitors. Other than the airstrip, a 2.9-mile trail, with 26 switchbacks and a 1,700 foot vertical drop, is the only way to access Kalaupapa. To traverse it, you must either hike it or ride down by mule.

OutsideOnline Empty Hawaii Kalaupapa Peninsula Molokai landmark leper colony trail switchbacks vertical drop hike mule
(Dylan Silver)

Between Kalaupapa’s founding in 1866 and the discovery of sulfone drugs in 1946, more than 8,000 victims of leprosy died here. Today, 15 former patients still live on the isolated peninsula—now a National Historic Park. Though no roads lead to the area, once a year, a barge drops off supplies like diesel fuel, appliances, and vehicles.

OutsideOnline Kalaupapa Peninsula 1866 Sulfone drugs leprosy leper colony patients no roads
(Dylan Silver)

The largest fringing reef in the United States—more than 340 square miles of coral— borders Molokai’s South Shore. Several operations offer scuba and dive tours. While the current and winds can cause issues for divers, there’s more often than not at least one site that can be visited, says Tim Forsberg, the captain and proprietor of Molokai Fish and Dive.

OutsideOnline Molokai South Shore coral fringing reef dive tour scuba current winds Molokai Fish and Dive
(Dylan Silver)

The Kalohi Channel between Lanai and Molokai is simply frothing with humpback whales. The big, white splashes from breaches can be seen from almost anywhere on the south side of the island. Of course, the best way to get a good look is to hire a boat. Though the best scenario involves lucking upon a “competition group”—a pod of male whales searching for a female—watching a mother and calf roll around in the waves isn’t bad either.

OutsideOnline Kalohi Channel Lanai Molokai humpback whales South Side mother calf roll waves
(Dylan Silver)

Filed To: Hawaii
Nicolas Henderson/Creative Commons )

San Marcos, Texas

Billed as the world’s toughest canoe race, the Texas Water Safari, held each June, is a four-day, 260-mile jaunt from the headwaters of the San Marcos River northeast of San Antonio to the small shrimping town of Seadrift on the Gulf Coast. There’s no prize money—just bragging rights for the winner. Any boat without a motor is allowed, and you’ll have to carry your own equipment and overnight gear. Food and water are provided at aid stations along the way. Entry fees start at $175 and increase as race day approaches.

The Ring

(Courtesy Quatro Hubbard)

Strasburg, Virginia

The Ring is a 71-mile trail running race in early September along the entire length of Virginia’s rough and rocky Massanutten Trail loop. To qualify, you need to have run a 50- or 100-mile race before the event and win a spot through the lottery system. Entry is free. Complete the run and you’ll become part of the tight-knit Fellowship of the Ring and be eligible for the Reverse Ring, which entails running the trail backwards in the middle of winter.


(David Silver)

Santa Fe, New Mexico

Each spring, competitors gather in Santa Fe’s historic plaza with a simple goal: be the first to reach 12,308-foot Deception Peak, 17 miles and 5,000 feet of elevation gain away. Competitors run or bike the first 15 miles to the local ski area before transitioning to their waiting ski-touring setups for the final push to the top. Time stops only when they’ve skied back down to the tailgate in the resort’s parking lot, which is funded by the modest entry fee of around $25. To add to the sufferfest, some participants sign up for the Expedition category, in which they strap their skis, skins, boots, and poles to their bikes for the long ride up. Start dates vary depending on snow conditions, but look for the event page to be posted on Facebook in late March or early April.

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