Hiker crossing volcanic cinder desert landscape

Hidden Trails 7-10: Ultimate Expert Challenges

For those who seek the impossible: wilderness crossings, alien landscapes, and routes that test every skill you possess

Written by a Local Expert

Kalani Miller

7. Kaupo Gap Wilderness Trail - Southeast Maui

Distance

12.5 miles

Elevation

3,800 ft

Difficulty

Expert Only

Best For

Wilderness

This trail pushes even experienced hikers to their limits. Starting from sea level near Kaupo village, you'll climb through multiple ecosystems to reach Haleakala's remote crater rim. Few attempt this trail, and fewer complete it successfully.

The path follows ancient Hawaiian routes up the mountain's steepest face. Early sections cross dry grasslands and scattered trees. As elevation increases, you enter cloud forest with thick mud and slippery roots. The final push crosses alpine desert to the crater rim.

WARNING: This is one of Hawaii's most dangerous trails. Water sources exist but can't be trusted. Weather varies dramatically with elevation. Emergency preparedness becomes critical on this remote route. Cell service doesn't exist. Rescue operations would take many hours or days.

Extreme Preparation Required

Elevation changes create dramatic ecosystem shifts. You'll start in coastal scrub at sea level and finish in high-altitude alpine desert. Each zone requires different skills and presents unique challenges. What works at one elevation fails completely at another.

The trail requires advanced navigation skills. Sections disappear completely, forcing you to read the landscape and choose your own route. GPS devices help but can't replace experience and judgment. Know how to navigate by terrain features and compass bearing.

Carry emergency shelter, first aid supplies, and signaling devices. Tell multiple people your exact plans and expected return time. Permits may be required depending on your exact route and destination. Check with Haleakala National Park for current regulations.

8. Red Hill Cinder Desert - Haleakala Backcountry

Distance

8.7 miles

Elevation

1,200 ft

Difficulty

Challenging

Best For

Mars-like

Beyond Haleakala's main tourist areas lies a vast cinder desert that few visitors explore. This backcountry area offers landscapes so alien they've been used for Mars mission training. You'll walk across fields of red and black volcanic cinder under enormous skies.

The trail starts from the main crater trail system but quickly diverges into unmarked wilderness. You'll follow compass bearings and terrain features across trackless desert. Navigation skills are essential - the landscape looks similar in all directions.

Rare plants dot this hostile environment. The famous silversword grows here in small populations. Mamane trees create islands of green in the red desert. Several endangered species exist nowhere else on earth. Observe from distance and never touch or collect anything.

Extreme Environment

Weather extremes challenge unprepared hikers. Daytime sun reflects off light-colored cinder, creating oven-like conditions. Nighttime temperatures can drop below freezing even in summer. Afternoon winds regularly exceed 50 mph, creating sandstorm conditions.

The desert's silence amazes first-time visitors. No birds sing here. No insects buzz. Only wind moves across the cinder, creating an eerie quiet that many find unsettling. This is one of the most isolated places in Hawaii.

Water doesn't exist in this environment. Carry more than you think you need - the dry air and high altitude increase dehydration risk. The nearest water source lies miles away at much lower elevation. This area offers no shelter from weather.

9. Waikamoi Ridge Trail - East Maui

Distance

6.8 miles

Elevation

2,100 ft

Difficulty

Challenging

Best For

Native Birds

High above the Hana Highway lies a trail through some of Hawaii's last pristine native forest. This ridge trail offers incredible bird watching opportunities and a chance to see what Hawaii looked like before human contact. The forest here exists much as it did centuries ago.

Access requires a difficult drive up rough forest roads. Four-wheel drive is recommended but not always required. Check road conditions before attempting - recent rains can make the access road impassable for regular vehicles.

Native bird populations here include some of Hawaii's rarest species. The Maui parrotbill lives only in these forests. Maui alauahio and akiapola calls echo through the trees. Moving quietly and patiently increases your chances of rare bird sightings.

Pristine Ecosystem

The trail winds through dense ohia and koa forest draped in native ferns and mosses. Tree ferns create a canopy overhead while rare native plants carpet the forest floor. Every step reveals plants and ecosystems that exist nowhere else on earth.

Cloud forest conditions create unique challenges. Visibility drops to just a few feet during heavy clouds. Temperatures can change 20 degrees when clouds roll in. Rain happens without warning, even from clear skies.

Conservation importance makes this area special but fragile. You're walking through habitat that supports endangered species found nowhere else. Stay on marked trails and avoid disturbing wildlife. Some research areas may be temporarily closed to protect nesting birds.

10. Kahakuloa Head Coastal Traverse - North Shore

Distance

5.5 miles

Elevation

1,800 ft

Difficulty

Very Challenging

Best For

Coastal Views

This expedition-level hike traverses Maui's most dramatic coastline, climbing over and around massive sea cliffs. The route follows ancient Hawaiian paths between isolated villages, passing archaeological sites and offering views that few people ever experience.

The traverse starts in Kahakuloa village and ends at Nakalele Point. You'll climb over 1,200-foot cliffs, scramble across lava benches, and navigate sections where the trail disappears completely. This isn't a maintained path - it's an adventure that requires serious outdoor skills.

Ancient Hawaiian sites dot the entire route. Stone platforms mark where temples once stood. Agricultural terraces show where families grew taro and sweet potato. Burial sites command prominent positions overlooking the ocean. All deserve respect and protection.

Extreme Exposure & Risk

Cliff exposure creates serious safety concerns. Ocean swells can send waves far inland, especially during winter months. Loose rock makes footing unstable near edges. Strong winds can affect balance and make rescue difficult if accidents occur.

Navigation challenges arise constantly. The trail forks, disappears, and reappears without warning. Ocean orientation helps but doesn't solve all navigation problems. Carry detailed topographic maps and know how to use compass and GPS devices.

Transportation requires planning since this is a one-way traverse. Most hikers arrange pickup at the endpoint or leave a second vehicle there. The road to Kahakuloa Head is narrow and winding but passable for most vehicles.