Portland sits between the Cascade Mountains and the Pacific Ocean, giving you access to an absurd variety of hiking within an hour's drive. Forest Park sprawls through 5,100 acres inside city limits—one of the largest urban forests in the United States. Drive 30 minutes east and you're in the Columbia River Gorge's waterfall corridor. Drive 90 minutes and you're on Mount Hood's alpine trails.
This guide covers 10 trails around Portland, from easy urban forest walks to challenging mountain climbs gaining 4,000+ feet. Each includes accurate distances, real elevation data, parking logistics, and honest assessments of trail conditions. Before heading out, make sure you have proper merino wool hiking clothes to handle Portland's infamous rain and year-round mud.
Portland's wet climate means mud dominates trail conditions 9 months per year. Waterproof boots aren't optional—they're survival gear. The trails are organized by drive time from downtown Portland.
How to Use This Guide
Four tools simplify trail selection:
Trail Picker Table: Filter by difficulty, drive time, season, and dog-friendliness.
Detailed Trail Breakdown: Complete descriptions with mileage, elevation, parking, and current conditions.
Logistics Section: Parking availability, Northwest Forest Pass requirements, transit options, and timing.
Seasonal Calendar: Best months for each trail—crucial for Portland's weather extremes.
Match your fitness level to a trail, check seasonal mud conditions, verify parking requirements, then go.
Trail Picker
| Trail | Difficulty | Distance | Elevation Gain | Drive Time | Best Season | Dog-Friendly |
|---|---|---|---|---|---|---|
| Wildwood Trail | Easy-Moderate | 1-30 miles | Variable | In city | Year-round | Yes |
| Multnomah Falls | Easy | 2.4 miles | 700 ft | 30 min | Year-round | Yes |
| Angel's Rest | Moderate | 4.8 miles | 1,500 ft | 35 min | Spring/Fall | Yes |
| Dog Mountain | Hard | 7 miles | 2,800 ft | 60 min | Spring (wildflowers) | No (ironically) |
| Tom Dick & Harry Mountain | Moderate-Hard | 5.8 miles | 1,700 ft | 75 min | Summer/Fall | Yes |
| Ramona Falls Loop | Moderate | 7.1 miles | 1,000 ft | 90 min | Summer/Fall | Yes |
| Mirror Lake | Moderate | 5.2 miles | 700 ft | 75 min | Summer/Fall | Yes |
| Eagle Creek | Moderate | 4-24 miles | 400-2,800 ft | 40 min | Spring/Summer/Fall | No (closed sections) |
| Timberline Trail | Hard | 41 miles | 8,000 ft | 90 min | Summer/Fall | Yes |
| Mount Hood Summit | Expert | 10-12 miles | 5,200 ft | 90 min | Summer | Technical climb |
Decision Framework
How much time do you have?
- Under 2 hours: Wildwood Trail sections, Multnomah Falls
- Half day: Angel's Rest, Mirror Lake, Tom Dick & Harry Mountain
- Full day: Dog Mountain, Ramona Falls, Eagle Creek (long version)
- Multi-day: Timberline Trail (requires backpacking)
What's your fitness level?
- New to hiking: Multnomah Falls (paved to bridge), Wildwood Trail (flat sections), Tryon Creek
- Regular exercise: Angel's Rest, Mirror Lake, Ramona Falls
- Experienced hiker: Dog Mountain, Tom Dick & Harry, Eagle Creek backcountry
- Technical climbers: Mount Hood summit (requires mountaineering skills)
What season?
- Summer (July-September): Everything is accessible. Dog Mountain wildflowers peak mid-May to June.
- Fall (October-November): Great temps, fall colors, but early snow possible on Mount Hood trails.
- Winter (December-March): Stick to low-elevation trails (Forest Park, Gorge waterfalls at base). Mount Hood trails require snowshoes or skis.
- Spring (April-June): Waterfall season—Gorge waterfalls are spectacular but trails are muddy. Dog Mountain wildflowers peak late May.
Logistics
| Trail | Parking | Fee | Permit | Transit | Best Arrival Time |
|---|---|---|---|---|---|
| Wildwood Trail | Multiple lots | Free | No | TriMet Bus | Anytime |
| Multnomah Falls | Large lot | Free | No | None | Before 9am weekends |
| Angel's Rest | Roadside | $5 day pass | No | None | Before 8am weekends |
| Dog Mountain | Small lot | $5 day pass | Required (lottery) | None | Early (permit time) |
| Mirror Lake | Medium lot | $5 day pass | No | None | Before 10am weekends |
| Ramona Falls | Good | $5 day pass | No | None | Before 10am weekends |
| Eagle Creek | Good (rebuilt) | $5 day pass | Required (timed entry) | None | Reserve in advance |
Northwest Forest Pass ($5/day or $30/year): Required at most trailheads outside city limits. Available at REI, ranger stations, or Recreation.gov. Seriously—rangers ticket constantly.
Dog Mountain Permit: Requires advance lottery reservation April 1-June 30 (peak wildflower season). Free lottery at Recreation.gov opens in early March. Outside permit season, no reservation needed but wildflowers are gone.
Eagle Creek Permit: Timed entry permits required year-round after 2017 fire reopening. Free but must reserve in advance at Recreation.gov. Limited daily capacity.
Parking notes: Multnomah Falls fills completely by 9am on summer weekends—arrive early or use shuttle from Rooster Rock State Park (seasonal). Dog Mountain has 30 parking spots and 200+ hikers on nice spring days—carpooling required. Angel's Rest roadside parking creates traffic jams on weekends.
Drive Time from Downtown Portland
Within City Limits:
- Wildwood Trail: 15 minutes to various trailheads
- Pittock Mansion: 15 minutes via Burnside
- Council Crest: 20 minutes via Terwilliger
- Tryon Creek: 15 minutes via I-5
30-45 minutes:
- Multnomah Falls: 30 minutes via I-84
- Angel's Rest: 35 minutes via I-84
- Latourell Falls: 30 minutes via I-84
- Eagle Creek: 40 minutes via I-84
60-90 minutes:
- Dog Mountain: 60 minutes via I-84 and SR-14 (Washington side)
- Mirror Lake: 75 minutes via US-26
- Tom Dick & Harry Mountain: 75 minutes via US-26
- Ramona Falls: 90 minutes via US-26 and forest roads
- Timberline Trail: 90 minutes to Timberline Lodge
Trail Breakdown
1. Multnomah Falls
Distance: 2.4 miles round trip (to top) Elevation gain: 700 feet Difficulty: Easy to Moderate Trailhead: Multnomah Falls Lodge, Historic Columbia River Hwy
Multnomah Falls drops 620 feet in two tiers—Oregon's tallest waterfall and the Columbia River Gorge's most visited site. The lower viewing area requires zero hiking. The paved trail to Benson Bridge (0.2 miles, easy) crosses between the falls' two tiers for classic photos.
The upper trail continues to the falls' top—another mile gaining 700 feet on switchbacks. The climb is steady but achievable for anyone with basic fitness. At the top, you see the falls from above and get Gorge views.
This trail gets absolutely mobbed. Summer weekends see 5,000+ visitors. Parking fills by 9am. The lodge, built in 1925, offers restrooms and a snack bar. A shuttle runs from Rooster Rock State Park on busy weekends (seasonal).
The falls flow year-round but peak volume hits in spring (March-May) from snowmelt and rain. Winter sees fewer crowds and sometimes ice formations on the falls' sides. The paved section to Benson Bridge is accessible year-round.
Dogs allowed on leash. The crowds and pavement make this less enjoyable for dogs than wilderness trails. Free parking but arrive very early on weekends.
2. Angel's Rest
Distance: 4.8 miles round trip Elevation gain: 1,500 feet Difficulty: Moderate Trailhead: Angel's Rest parking area, Historic Columbia River Hwy
Angel's Rest climbs from the Columbia River to a rocky overlook 1,500 feet above the Gorge. The trail switchbacks relentlessly through forest before breaking into open rocky terrain near the summit. The final scramble requires hands on rock but isn't technical.
The summit offers 360-degree views—Columbia River Gorge in both directions, Mount Hood, Mount Adams, and Portland's skyline on clear days. It's one of the Gorge's best viewpoints for the effort required.
The trail gets heavy use. Weekend mornings see steady traffic. The parking area is roadside I-84 pullouts—arrive before 8am on nice days or park 0.5+ miles away on the highway shoulder. Afternoons bring intense sun on the exposed upper sections.
Spring and fall provide optimal temps. Summer gets hot on the exposed rock sections—bring extra water. Winter stays mostly snow-free but can be icy. The trail drains fairly well but expect mud in wet seasons.
Dogs allowed on leash. Bring water for them—no water sources on trail. The rocky summit can be tough on paws. Northwest Forest Pass required ($5/day).
3. Dog Mountain
Distance: 7 miles round trip Elevation gain: 2,800 feet Difficulty: Hard Trailhead: Dog Mountain Trailhead, SR-14, Stevenson, WA
Dog Mountain is brutal and spectacular. The trail climbs 2,800 feet in 3.5 miles—relentless switchbacks through forest opening to wildflower meadows that explode with color mid-May through June. Balsamroot, lupine, and paintbrush cover entire hillsides.
Two routes reach the summit: the old trail (steeper, more direct) and the new trail (longer, slightly gentler grade). Most hikers ascend the old trail and descend the new. Both options are punishing.
The summit plateau spreads across wildflower meadows with Mount Hood, Mount Adams, and the Columbia River Gorge dominating the views. On peak wildflower weekends, you share the summit with 200+ hikers.
Permit system: April 1-June 30 requires advance lottery permits (free). The lottery opens early March at Recreation.gov. Outside permit season, no reservation needed but wildflowers are gone by July. The parking lot holds 30 cars—carpooling is essential during permit season.
Ironically, dogs are NOT allowed on Dog Mountain. The name comes from Lewis and Clark's reference to "dogfish" in the Columbia River below. Bring 2-3 liters of water—no water sources on trail. The exposed sections get hot even in May. Hiking in spring requires layers for variable temps.
4. Wildwood Trail (Forest Park)
Distance: 1-30 miles (sections or full trail) Elevation gain: Variable (200-2,000+ feet) Difficulty: Easy to Moderate Trailhead: Multiple access points from NW Portland
The Wildwood Trail runs 30.2 miles through Forest Park—one of America's longest urban trails. You don't hike the whole thing in one go. Instead, pick sections matching your time and fitness.
Popular sections:
- Lower Macleay to Pittock Mansion (5 miles, 900 ft gain): Starts in fern-filled canyon, climbs to historic mansion with city views
- Thurman Street to Germantown Road (6 miles, 800 ft gain): Classic Forest Park experience through dense forest
- Any segment (customize length): Use cross trails to create loops or shorter out-and-backs
Forest Park stays surprisingly wild despite sitting in Portland. The trail winds through Douglas fir and hemlock forest with minimal views but excellent solitude. The forest creates a sound buffer—road noise fades within 0.25 miles.
Trail conditions are muddy 9 months per year. "Muddy" is an understatement—it's boot-sucking, slippery mud from October through June. Summer (July-September) provides the best conditions but even then, shaded sections stay damp.
Free parking at numerous trailheads. TriMet buses serve multiple access points. Dogs allowed on leash and love this trail—the forest terrain provides endless smells. Year-round access makes this Portland's go-to rainy day hike.
5. Eagle Creek Trail
Distance: 4-24 miles depending on destination Elevation gain: 400-2,800 feet Difficulty: Moderate Trailhead: Eagle Creek Recreation Area, I-84
Eagle Creek carved a dramatic gorge with multiple waterfalls, hanging gardens, and cliff-side trail sections. The trail follows the creek through old-growth forest, passing Punch Bowl Falls (2 miles), High Bridge (3.3 miles), and Tunnel Falls (6 miles where the trail goes behind the waterfall).
The 2017 Eagle Creek Fire burned 50,000 acres. The trail reopened in 2022 after extensive rebuilding. Sections show fire damage but recovery is remarkable. The trail is as spectacular as ever with new bridges and improved tread.
Timed entry permits required year-round (free, reserve at Recreation.gov). Limited daily capacity prevents overcrowding. The permit system works well—the trail feels less crowded than pre-fire despite heavy demand.
Punch Bowl Falls (4 miles round trip) makes a great shorter destination. Tunnel Falls (12 miles round trip) is the classic full-day hike. The trail continues 13+ miles to Wahtum Lake for backpackers.
The trail has cliff exposure—watch kids closely. Some sections include cables for stability. Dogs allowed on leash but consider the exposure and length. Bring 2+ liters of water. Northwest Forest Pass required.
6. Ramona Falls Loop
Distance: 7.1 miles Elevation gain: 1,000 feet Difficulty: Moderate Trailhead: Ramona Falls Trailhead (requires 4 miles rough forest road)
Ramona Falls cascades 120 feet over a columnar basalt wall creating a fan of water. The loop trail crosses the Sandy River on a suspension bridge, winds through old-growth forest, and reaches the falls at 3.5 miles.
The clockwise direction (recommended) saves the falls for the midpoint reward. The counterclockwise route hits the falls first but has boring forest on the return. Either way, it's a pleasant moderate hike through classic Mount Hood National Forest.
Access requires 2.5 miles of rough, potholed forest road (FR-1825) from paved Lolo Pass Road. The road is passable in regular cars but requires slow, careful driving. High clearance helps but isn't mandatory. The rough road filters out some crowds.
Summer and fall provide optimal conditions. The trail drains well but can be muddy in spring. Winter closes access due to snow on forest roads. The Sandy River crossing can be dangerous in spring high water—use the bridge, don't attempt fording.
Dogs allowed on leash. Bring water—the only reliable source is the Sandy River at the start. Northwest Forest Pass required. Parking lot holds 30+ cars and fills on nice weekends. Arrive before 10am.
7. Mirror Lake
Distance: 5.2 miles round trip Elevation gain: 700 feet Difficulty: Moderate Trailhead: Mirror Lake Trailhead, US-26
Mirror Lake offers classic Mount Hood views reflected in a subalpine lake. The trail climbs gradually through forest for 2.5 miles before reaching the lake at 4,050 feet. On calm mornings, Mount Hood's reflection in the lake creates perfect photo conditions.
Continue 0.6 miles and 450 feet higher to Tom Dick & Harry Mountain's summit (see next entry) for aerial lake views. Most hikers stop at the lake—the summit extension adds difficulty but rewards with better views.
The trail gets heavy use—it's accessible, scenic, and family-friendly. Summer weekends see steady traffic. The lake can be crowded with people swimming, picnicking, and photographing. Early morning provides solitude and best light for Mount Hood reflections.
Summer and fall are optimal. The trail usually opens by late June once snow melts. Fall (September-October) brings fewer crowds and larch color. Winter buries the trail under deep snow—snowshoes or skis required.
Dogs allowed on leash. Bring water—the lake water should be filtered. The lake area has limited established camping but backpackers do camp (wilderness rules apply). Northwest Forest Pass required. Parking fills by 10am on nice summer weekends.
8. Tom Dick & Harry Mountain
Distance: 5.8 miles round trip (from Mirror Lake) Elevation gain: 1,700 feet total Difficulty: Moderate to Hard Trailhead: Mirror Lake Trailhead, US-26
Tom Dick & Harry Mountain (yes, really) rises above Mirror Lake to 5,066 feet. The summit offers spectacular 360-degree views: Mount Hood dominates the north, Mount Jefferson appears south, and Mirror Lake spreads below.
From the Mirror Lake junction (2.5 miles), the summit trail climbs 450 steep feet in 0.6 miles. The grade is punishing after the approach hike. The summit plateau includes three distinct high points—"Tom," "Dick," and "Harry"—explore all three for complete views.
Many hikers skip this summit extension and stop at Mirror Lake. That's their loss. The summit views surpass the lake views significantly. The effort is worth it.
Late summer and fall provide optimal conditions. Snow lingers into July some years. The exposed summit can be windy and cold—bring layers even on warm days. Proper layering with merino base layers handles the temperature swings.
Dogs allowed but consider the steep summit pitch. Bring extra water for the climb. Northwest Forest Pass required. Same parking as Mirror Lake—fills early on weekends.
9. Timberline Trail
Distance: 41 miles (full circumnavigation) Elevation gain: ~8,000 feet total Difficulty: Hard (requires backpacking) Trailhead: Multiple access points (Timberline Lodge common start)
The Timberline Trail circles Mount Hood at 5,000-7,000 feet elevation. The 41-mile loop typically requires 3-5 days of backpacking. It's one of America's premier mountain trails—dramatic alpine scenery, snowfields, glacial rivers, and constant Mount Hood views.
The trail crosses multiple glacial drainages requiring unbridged stream crossings. These crossings range from ankle-deep (late summer) to thigh-deep, swift, and dangerous (early summer). Timing matters—crossings are safest in morning when glacial melt is lowest.
Sections include:
- Paradise Park (wildflower meadows)
- Zigzag Canyon (dramatic gorge)
- Cooper Spur (highest point at 7,300 feet)
- Eliot Creek (most challenging crossing)
Permits are not required but wilderness regulations apply (camp 200 feet from water and trails). Most hikers go clockwise starting from Timberline Lodge. Water is abundant. Wildlife includes black bears—proper food storage required.
Summer (mid-July through September) provides optimal conditions. Early summer has snow and dangerous river crossings. Fall brings fewer crowds but weather becomes unpredictable. This is a serious backpacking trip requiring navigation skills, river crossing experience, and self-sufficiency.
Dogs allowed but consider the river crossings and alpine terrain. This isn't a casual dog backpacking trip. Backpacking preparation is essential.
10. Tryon Creek State Natural Area
Distance: 3-8 miles of interconnected trails Elevation gain: 300 feet Difficulty: Easy Trailhead: Main Parking Area, Terwilliger Blvd, Portland
Tryon Creek offers easy urban hiking in a 658-acre forested canyon within Portland. The trail system includes 8 miles of unpaved trails and 3 miles of paved paths. It's perfect for families, beginners, or rainy day hiking close to home.
The trails wind along Tryon Creek through second-growth forest. The nature center (staffed weekends) provides trail maps and educational displays. The paved paths are wheelchair accessible and work well for strollers.
This isn't a destination hike—it's a convenient urban forest escape. Don't expect dramatic views or challenging terrain. The forest provides solitude and bird watching within city limits.
Dogs allowed on designated trails only—check signs. Bikes allowed on paved trails only. Free parking. The trails stay muddy most of the year but remain hikeable. Year-round access makes this a reliable rainy day option.
Hiking with Kids, Dogs, and Mixed Groups
For families with kids: Multnomah Falls (to bridge), Mirror Lake, and Tryon Creek work best. All have interesting features (waterfalls, lake, forest) without excessive distance. Wildwood Trail sections allow customizing length to kids' abilities. Avoid Angel's Rest and Dog Mountain—too steep and exposed for young children.
Dog-friendly trails: Most trails allow leashed dogs: Wildwood Trail, Multnomah Falls, Angel's Rest, Mirror Lake, Ramona Falls, and Timberline Trail. Dogs NOT allowed: Dog Mountain (ironically), Eagle Creek (during permit season). Always bring water—many trails lack water sources. Hiking with your dog in Portland's mud requires post-hike cleanup.
Mixed-ability groups: Wildwood Trail and Tryon Creek accommodate all fitness levels—multiple bailout options and varying loop lengths. Multnomah Falls works if some group members hike to the top while others wait at the bridge. Ramona Falls offers moderate terrain suitable for most hikers with basic fitness.
What to Wear and Pack
Portland's climate means rain dominates 8-9 months per year. Waterproof everything isn't optional—it's survival.
Footwear: Waterproof hiking boots with good tread. Portland trails are muddy October-June. The combination of rain, mud, and tree roots creates the slipperiest conditions imaginable. Trail runners work in summer (July-September) but even then, some sections stay damp.
Clothing: Winter/Spring/Fall (October-May): Waterproof layers are essential. Rain can last weeks. Start with merino base layers, add fleece mid-layer, and top with waterproof shell. Pack rain pants—getting soaked ruins hikes.
Summer (June-September): Mild and dry. Merino t-shirts handle the temps. Still bring a rain jacket—summer storms happen. Mornings can be 50°F while afternoons hit 75°F.
Essential gear:
- Water: 2 liters minimum, 3 liters for longer/higher trails
- Snacks: Trail mix, bars, fruit
- First aid kit
- Waterproof jacket (year-round)
- Merino hiking socks (prevent blisters in wet conditions)
- Rain pants (October-May)
- Gloves and beanie (higher elevations, even summer)
- Phone/GPS with offline maps
- Headlamp (days are short November-February)
Packing by season:
| Item | Spring/Fall | Summer | Winter |
|---|---|---|---|
| Merino base layer | Essential | Optional | Essential |
| Waterproof jacket | Essential | Recommended | Essential |
| Rain pants | Essential | Optional | Essential |
| Merino socks | Essential | Essential | Essential |
| Extra water | 2L | 2-3L | 1.5L |
| Gaiters | Recommended | Optional | Essential (snow) |
Seasonal Planning
| Month | Best Trails | Weather | Trail Conditions | Crowds |
|---|---|---|---|---|
| Jan-Feb | Forest Park, Gorge low elevations | Cold (40-50°F), very wet | Muddy | Low |
| Mar-Apr | Forest Park, Gorge waterfalls | Cool (50-60°F), rainy | Very muddy, early flowers | Moderate |
| May-Jun | Dog Mountain (wildflowers), lower elevation trails | Mild (60-70°F), drying | Mud decreasing, snowmelt rivers high | High (Dog Mtn) |
| Jul-Aug | All Mount Hood trails, high elevation hikes | Warm (75-85°F), dry | Best conditions | High |
| Sep-Oct | All trails, fall colors | Mild (60-70°F), occasional rain | Good conditions | Moderate |
| Nov-Dec | Forest Park, Gorge low elevations | Cold (40-50°F), very wet | Muddy, higher trails get snow | Low |
Best overall season: July-September. Trails dry out, Mount Hood trails open, and weather is reliable. This is Portland hiking's brief summer window.
Spring wildflowers: Dog Mountain peaks mid-May to mid-June. Arrive early for parking.
Fall colors: October brings fall foliage to Forest Park and Gorge. Fewer crowds than summer.
Winter considerations: November-March is constant rain. Stick to low-elevation trails (Forest Park, Gorge base trails). Mount Hood trails require snowshoes. Many forest roads close.
Safety, Weather, and Trail Etiquette
Weather risks:
| Season | Primary Risk | Severity | Prevention |
|---|---|---|---|
| Summer | Heat on exposed trails | Moderate | Start early, extra water |
| Spring | Flooding, river crossings | High | Check conditions, avoid high water |
| Fall | Sudden cold/rain | Moderate | Layer properly, check forecast |
| Winter | Hypothermia, snow | High | Proper gear, know when to turn back |
| Year-round | Mud, slippery trails | Moderate | Good boots, trekking poles |
Portland rain reality: Portland gets 37 inches of rain annually—most falling October-May. This isn't heavy downpours—it's steady drizzle lasting days or weeks. Trails never fully dry during wet season. Embrace the mud or wait for summer.
River crossing safety: Eagle Creek, Ramona Falls, and Timberline Trail cross rivers. Spring snowmelt creates dangerous conditions. Cross in morning when water is lowest. Unbuckle pack waist belt for quick release if you fall. Turn back if water is above knee-deep or flowing fast.
Wildlife: Black bears exist but encounters are rare. Cougars are present but rarely seen. Make noise in dense forest. The biggest wildlife risk is poison oak—widespread on Gorge trails. Learn to identify it.
Trail etiquette:
- Uphill hikers have right of way
- Bikers yield to hikers, hikers yield to horses
- Keep dogs leashed (required on all trails)
- Pack out all trash including orange peels
- Stay on trail—muddy season causes widening from people avoiding mud puddles
Emergency preparedness: Cell service is good in Gorge and Forest Park. Spotty on Mount Hood backcountry. Download offline maps. Tell someone your plan and expected return time for remote hikes.
Sample Itineraries
One Day: Portland Highlights
Morning: Multnomah Falls (8am start, 2 hours). Classic Oregon waterfall with paved access and summit climb option.
Afternoon: Angel's Rest (1pm, 3 hours). Gorge viewpoint hike with moderate challenge.
Total: 7 miles, moderate effort, back by 5pm. Showcases Portland's waterfall and viewpoint hiking.
Weekend: Gorge and Mount Hood
Day 1:
- Morning: Dog Mountain (arrive with permit time, 4-5 hours). Brutal climb, spectacular wildflower meadows (May-June).
- Afternoon: Recovery
Day 2:
- Morning: Mirror Lake to Tom Dick & Harry summit (6-7 hours). Alpine lake and summit views of Mount Hood.
Total: Two days mixing Gorge and Mount Hood classics. Requires solid fitness.
Weekend: Easier Exploration
Day 1:
- Morning: Ramona Falls Loop (4-5 hours). Beautiful waterfall and forest.
- Afternoon: Timberline Lodge visit, short walks
Day 2:
- Morning: Wildwood Trail section (3-4 hours). Urban forest hiking.
- Afternoon: Multnomah Falls (1-2 hours). End with the classic.
Total: Moderate hiking showcasing Portland's range without crushing difficulty.
Three-Day: Complete Experience
Day 1: Urban Trails
- Morning: Wildwood Trail to Pittock Mansion (3 hours)
- Afternoon: Explore Portland
Day 2: Columbia River Gorge
- Morning: Eagle Creek to Punch Bowl Falls (4 hours, need permit)
- Afternoon: Multnomah Falls (2 hours)
Day 3: Mount Hood
- Full day: Ramona Falls Loop (5 hours) or Mirror Lake + Tom Dick & Harry summit (6-7 hours)
Total: Three days experiencing urban forest, Gorge waterfalls, and Mount Hood alpine trails.
Navigation Tools
AllTrails ($36/year for Pro): Essential. Download offline maps for Mount Hood trails where cell service is spotty. Check recent reviews for trail conditions—crucial in Portland's variable weather.
Gaia GPS ($40/year): Better topographic maps. Useful for complex areas like Timberline Trail or Eagle Creek backcountry.
USFS Trail Conditions: Check Mount Hood National Forest website for current trail conditions, snow levels, and road closures before driving out.
Weather Apps: Portland weather changes fast. Check forecast morning-of, not night before. Mountain weather differs significantly from Portland—Mount Hood can be 20-30°F cooler.
Cell Service: Good in Gorge and Forest Park. Spotty on Mount Hood above 4,000 feet. Download offline maps before leaving for mountain trails.
FAQ
What's the best time of year to hike near Portland? Summer (July-September) offers the best conditions—dry trails, all high-elevation trails open, and reliable weather. Spring brings waterfalls and wildflowers but constant rain and mud. Fall has good weather but shorter days. Winter is rainy—stick to low-elevation trails. Check out winter hiking tips for cold-weather preparation.
Are there dog-friendly trails near Portland? Most trails allow leashed dogs: Forest Park, Multnomah Falls, Angel's Rest, Mirror Lake, Ramona Falls. Dogs NOT allowed: Dog Mountain, Eagle Creek (during permit season). Portland's mud makes post-hike dog cleanup mandatory. Read more about hiking with dogs.
What should I pack for hiking near Portland? Waterproof boots, rain jacket, and merino wool layers are essential October-June. Even in summer, bring rain gear. Pack 2-3 liters water, snacks, first aid kit, and merino hiking socks. Check full packing list in "What to Wear and Pack" section.
Which trails are best for beginners? Start with Multnomah Falls (to bridge), Tryon Creek, or easy Forest Park sections. All have minimal elevation and good trail conditions. Mirror Lake works for beginners with moderate fitness. Avoid Angel's Rest, Dog Mountain, and Tom Dick & Harry until you've built experience.
Do I need permits for hiking near Portland? Northwest Forest Pass ($5/day or $30/year) required at most Gorge and Mount Hood trailheads. Dog Mountain requires lottery permit April-June. Eagle Creek requires free timed-entry permit year-round (reserve in advance). Forest Park trails are permit-free.
How muddy are Portland trails? Very muddy October-June. "Portland mud" is legendary—slippery, boot-sucking, and unavoidable. Waterproof boots with aggressive tread are mandatory. Summer (July-September) provides the only reliably dry conditions. Embrace the mud or wait for summer.
Common Mistakes to Avoid
Not having waterproof boots: Portland trails are muddy 9 months per year. Trail runners work in summer only. Waterproof hiking boots with good tread aren't optional—they're survival gear. The mud is slippery beyond belief. People underestimate this constantly.
Forgetting Northwest Forest Pass: $5 day pass or $30 annual pass required at most trailheads outside city limits. Rangers ticket regularly. Buy passes at REI, ranger stations, or online at Recreation.gov before leaving.
Skipping permit reservations: Dog Mountain (April-June) and Eagle Creek (year-round) require advance reservations. You cannot hike without them. Make Dog Mountain lottery reservations in March. Make Eagle Creek timed-entry reservations days or weeks ahead. Show up without permits and you're turned away.
Underestimating Dog Mountain difficulty: It's called "Dog" Mountain but it's a beast. 2,800 feet in 3.5 miles with no shade and relentless grade. People see "7 miles round trip" and assume it's moderate. It's not. This trail destroys unprepared hikers. The wildflowers are worth it but come prepared.
Arriving late to popular trailheads: Multnomah Falls fills by 9am weekends. Dog Mountain parking holds 30 cars for 200+ hikers on peak days. Angel's Rest roadside parking creates traffic jams by 9am. Mirror Lake fills by 10am summer weekends. Arrive early or deal with parking nightmares.
Wearing cotton in rain: Cotton holds moisture and stays wet, causing rapid heat loss. Portland's constant rain makes cotton dangerous. Use moisture-wicking fabrics instead. Merino wool handles Portland's wet conditions better than any other fabric—it breathes, wicks moisture, and stays warm even when damp.
Not checking trail conditions before driving: Forest roads to Mount Hood trails close in winter. Rivers flood in spring making crossings dangerous. Check USFS trail condition reports before driving an hour to closed trails. Recent AllTrails reviews reveal current conditions.
Conclusion
Portland's hiking diversity rivals anywhere in America. You can walk through old-growth urban forest in the morning, stand beneath 620-foot waterfalls at lunch, and summit alpine peaks for sunset—all within 90 minutes of downtown. The trails range from wheelchair-accessible paved paths to technical mountaineering routes gaining 5,000+ feet.
Start with easier trails near the city—Forest Park, Multnomah Falls, or Tryon Creek. Build up to moderate terrain at Angel's Rest, Mirror Lake, and Ramona Falls. Save Dog Mountain, Timberline Trail, and Mount Hood summit for when you're ready for serious elevation gain and full-day commitments.
Before your next hike, stock up on gear from our men's outdoor collection or women's outdoor collection. Don't forget quality merino wool socks and base layers to handle Portland's rain and mud. Check out our hiking tips for beginners if you're new to hiking.
Check the weather forecast, buy your Northwest Forest Pass, make required reservations, and wear waterproof boots. The trails are waiting.
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