Portland Top › Guides › Hard Hiking Trails
Hard Hiking Trails near Portland
108 hard hiking trails near Portland, each read off OpenStreetMap: a waterfall or viewpoint counts only where it lies on the trail itself, and length is measured along it. Alphabetical — not ranked.
Angel's Rest Trail
Trailhead near Corbett4.6 milesHard · ~4 hoursWaterfallsAngora Peak Trail
Trailhead near Manzanita4 milesHard · ~3.5 hoursArch Cape to Cape Falcon Trail
Trailhead near Manzanita4.1 milesHard · ~3.5 hoursBadger Creek Trail
Trailhead near Government Camp12.1 milesHard · ~9.5 hoursBagby Trail #544
Trailhead near Detroit10.7 milesHard · ~9 hoursBarlow Butte Trail #670
Trailhead near Government Camp4.9 milesHard · ~5 hoursBattle Ax Creek Trail #3339
Trailhead near Detroit6.1 milesHard · ~5 hoursBlue Box Trail
Trailhead near Government Camp3.6 milesHard · ~3 hoursBluegrass Ridge Trail #647
Trailhead near Government Camp6.1 milesHard · ~5 hoursBonanza Trail #786
Trailhead near Welches4.8 milesHard · ~4.5 hoursBottle Prairie Trail #455
Trailhead near Parkdale4.7 milesHard · ~4 hoursBoulder Ridge Trail #783A
Trailhead near Welches3.6 milesHard · ~3.5 hoursBull of the Woods Trail
Trailhead near Detroit4 milesHard · ~3.5 hoursBurnt Granite Trail #595
Trailhead near Ripplebrook4.1 milesHard · ~3.5 hoursBurnt Lake Trail #772, Rhododendron
Trailhead near Rhododendron2 locations4.1 milesHard · ~3.5 hoursCast Creek Trail #773
Trailhead near Rhododendron5 milesHard · ~4.5 hoursCatamount Trail
Trailhead near Stayton5.3 milesHard · ~4 hoursCedar Creek Trail #457
Trailhead near Government Camp4.5 milesHard · ~4 hoursClackamas River Trail #715
Trailhead near Three Lynx7.5 milesHard · ~6.5 hoursClimber's Trail
Trailhead near Idanha2.5 milesHard · ~3.5 hoursCooks Meadow Trail #639
Trailhead near Government Camp6.6 milesHard · ~5.5 hoursCool Creek Trail #794
Trailhead near Rhododendron3.1 milesHard · ~3.5 hoursCorral Springs Trail #507
Trailhead near Estacada3.2 milesHard · ~3 hoursCrane Creek Trail #478
Trailhead near Government Camp4.9 milesHard · ~4 hoursCrescent Park Greenway (proposed segment)
Trailhead near Helvetia18.3 milesHard · ~12 hoursCripple Creek Trail #702
Trailhead near Three Lynx3.2 milesHard · ~3.5 hoursCrown Zellerbach Trail
Trailhead near Vernonia21.8 milesHard · ~15.5 hoursWaterfallsDickey Creek Trail #553
Trailhead near Detroit6 milesHard · ~5 hoursDivide Trail
Trailhead near Government Camp7.7 milesHard · ~6.5 hoursDog River Trail #675
Trailhead near Parkdale5.3 milesHard · ~4.5 hoursDouglas Cabin Trail
Trailhead near Government Camp3.6 milesHard · ~3.5 hoursDouglas Trail #781
Trailhead near Welches7 milesHard · ~6 hoursDry Creek Falls Hike
Trailhead near Cascade Locks4.2 milesHard · ~3.5 hoursDry Ridge Trail #518
Trailhead near Three Lynx5.2 milesHard · ~5 hoursEagle Creek Trail
Trailhead near Cascade Locks13 milesHard · ~11 hoursWaterfallsEagle Creek Trail #501
Trailhead near Sandy6.4 milesHard · ~5 hoursEagle-Benson Trail #434
Trailhead near Cascade Locks2.6 milesHard · ~3 hoursWaterfallsEagle-Tanner Trail #433
Trailhead near Cascade Locks4.3 milesHard · ~4 hoursEightmile Loop Trail #496
Trailhead near Parkdale5.6 milesHard · ~4.5 hoursElk Cove Trail #631
Trailhead near Government Camp4.7 milesHard · ~4 hoursElk Creek Trail
Trailhead near Lee's Camp3.6 milesHard · ~3.5 hoursElk Lake Creek Trail #559
Trailhead near Detroit8.6 milesHard · ~7 hoursElk Meadows Trail #645
Trailhead near Government Camp8.6 milesHard · ~7 hoursElk Mountain-Kings Mountain Loop
Trailhead near Lee's Camp9.7 miles loopHard · ~5 hoursElkhorn Ridge Trail #3347
Trailhead near Gates5.4 milesHard · ~5.5 hoursFanton Trail #505
Trailhead near Estacada4.3 milesHard · ~3.5 hoursFrench Creek Trail #3349
Trailhead near Detroit5.3 milesHard · ~4.5 hoursGales Creek Trail
Trailhead near Forest Grove11.2 milesHard · ~9.5 hoursGordon Butte Trail #470A
Trailhead near Government Camp2.8 milesHard · ~3 hoursGorge Trail, Cascade Locks
Trailhead near Cascade Locks9.1 milesHard · ~7.5 hoursWaterfallsGorge Trail, Mount Hood National Forest
Trailhead near Dodson4.9 milesHard · ~4 hoursWaterfallsGorton Creek Trail #408
Trailhead near Cascade Locks8.8 milesHard · ~8 hoursGrouse Point Trail #517
Trailhead near Three Lynx8.7 milesHard · ~8.5 hoursGumjuwac Trail
Trailhead near Government Camp4.5 milesHard · ~4.5 hoursGunsight Trail
Trailhead near Government Camp5 milesHard · ~4 hoursHagg Lake Trail
Trailhead near Forest Grove13.4 miles loopHard · ~5 hoursHerman Creek Trail
Trailhead near Cascade Locks10.1 milesHard · ~9 hoursWaterfallsHidden Lake Trail #779
Trailhead near Government Camp4.2 milesHard · ~4 hoursHigh Ridge Trail
Trailhead near Molalla7.6 milesHard · ~7 hoursHorseshoe Ridge Trail #774
Trailhead near Rhododendron5.1 milesHard · ~4.5 hoursHorsetail Creek Trail #425
Trailhead near Cascade Locks5 milesHard · ~4.5 hoursHunchback Trail #793
Trailhead near Welches9.1 milesHard · ~9 hoursImage Creek Trail
Trailhead near Elkhorn5 milesHard · ~4.5 hoursJackpot Meadows Trail #492
Trailhead near Government Camp4.4 milesHard · ~3.5 hoursLarch Mountain Trail
Trailhead near Troutdale6.6 milesHard · ~6.5 hoursWaterfallsLewis and Clark Discovery Trail - Oregon Coast Trail
Trailhead near Seaside3.7 milesHard · ~3 hoursMazama Trail #625
Trailhead near Government Camp3.6 milesHard · ~3.5 hoursMcIntyre Ridge Trail #782
Trailhead near Welches5.8 milesHard · ~5 hoursMoffett Creek Trail #430
Trailhead near Cascade Locks4.4 milesHard · ~4.5 hoursMother Lodge Trail #558
Trailhead near Detroit5.8 milesHard · ~5 hoursMount Defiance Trail #413
Trailhead near Hood River6.2 milesHard · ~7 hoursWaterfallsNasty Rock Trail #3356
Trailhead near Gates2.8 milesHard · ~3.5 hoursNesmith Point Trail #428
Trailhead near Cascade Locks4 milesHard · ~4.5 hoursNick Eaton Trail #447
Trailhead near Cascade Locks4 milesHard · ~4 hoursOlallie Butte Trail
Trailhead near Idanha3.5 milesHard · ~3.5 hoursOneonta Trail
Trailhead near Sandy8.2 milesHard · ~7.5 hoursWaterfallsParadise Park Trail #778
Trailhead near Government Camp6.5 milesHard · ~5.5 hoursPerimeter Trail, Silver Falls State Park
Trailhead near Stayton5.6 milesHard · ~4.5 hoursPinnacle Ridge Trail #630
Trailhead near Government Camp3.3 milesHard · ~3 hoursPioneer-Indian Trail
Trailhead near Beaver7.4 milesHard · ~6 hoursPlaza Trail #783
Trailhead near Welches8.6 milesHard · ~7.5 hoursPolallie Ridge Trail #643A
Trailhead near Government Camp3.1 milesHard · ~3 hoursRed Lake Trail #719
Trailhead near Idanha5.3 milesHard · ~4.5 hoursRhododendron Ridge Trail #564
Trailhead near Ripplebrook6.4 milesHard · ~5 hoursRiverside Trail #723
Trailhead near Ripplebrook3.9 milesHard · ~3.5 hoursSalmon Butte Trail
Trailhead near Rhododendron5.4 milesHard · ~5 hoursSalmon River Trail #742
Trailhead near Rhododendron13 milesHard · ~10 hoursSchool Canyon Trail #468
Trailhead near Government Camp3.4 milesHard · ~3 hoursSouth Breitenbush Trail #3375
Trailhead near Idanha6.1 milesHard · ~5.5 hoursStarvation Ridge Trail #414
Trailhead near Hood River3.4 milesHard · ~4 hoursWaterfallsStorey Burn Trail
Trailhead near Forest Grove3.9 milesHard · ~3.5 hoursSurveyor's Ridge Trail #688, Hood River
Trailhead near Hood River11.1 milesHard · ~9 hoursTable Rock Trail
Trailhead near Elkhorn3.5 milesHard · ~3 hoursThree Mile Trail
Trailhead near Government Camp4.4 milesHard · ~3.5 hoursTimberline To Town Trail #756
Trailhead near Government Camp4.9 milesHard · ~4 hoursTriangulation Trail #3373
Trailhead near Idanha6.1 milesHard · ~5 hoursTumble Ridge Trail #3380
Trailhead near Detroit5.1 milesHard · ~5 hoursTwin Lakes Trail #573
Trailhead near Detroit4.5 milesHard · ~4 hoursTygh Creek Trail #460
Trailhead near Government Camp6.4 milesHard · ~5.5 hoursWelcome Lakes Trail
Trailhead near Detroit4 milesHard · ~4 hoursWhetstone Mountain Trail #3369, Willamette National Forest
Trailhead near Detroit5 milesHard · ~5 hoursWhitewater Trail #3429
Trailhead near Idanha4 milesHard · ~3.5 hoursWhoopdee Trail (2021 Reroute)
Trailhead near Hood River4.5 milesHard · ~3.5 hoursWilson River Trail, Tillamook
Trailhead near Tillamook15.8 milesHard · ~13 hoursWaterfallsWyeth Trail #411
Trailhead near Hood River6.9 milesHard · ~7 hoursWygant Trail
Trailhead near Hood River4 milesHard · ~3.5 hoursYocum Ridge Trail #771
Trailhead near Government Camp5 milesHard · ~4.5 hoursZigzag Mountain Trail #775
Trailhead near Rhododendron12.7 milesHard · ~11.5 hours