Start by using reputable trail resources that allow you to filter by distance, elevation gain, and difficulty rating, such as local park websites and established hiking platforms. Match trail stats to your current fitness—for beginners, look for hikes under 5 miles with moderate elevation; for intermediate and advanced hikers, gradually increase distance and elevation gain. Read recent user reviews for updates on trail conditions, closures, and crowd levels. Cross-reference multiple sources, including the Portland Parks & Recreation and Forest Park Conservancy websites, to confirm accuracy. Finally, consider your experience with steep terrain, exposure, and navigation when deciding whether a trail is appropriate for you.

Several regions around Portland stand out for consistently excellent hiking. Within city limits, Forest Park offers an extensive network of wooded trails with varied distances and relatively gentle grades. To the east, the Columbia River Gorge provides more dramatic terrain, waterfalls, and viewpoints, with hikes ranging from short, paved paths to steep, strenuous climbs. To the south and west, Tryon Creek State Natural Area, Powell Butte, and the Tualatin Mountains offer forested and meadow trails with less exposure and easier access. For alpine-style hikes with seasonal wildflowers and expansive views, look to the Mount Hood National Forest, typically best from late spring through early fall.

Hiking is possible year-round in the Portland area, but conditions and trail options vary by season. Late spring through early fall generally offers the widest range of accessible trails, with snow-free routes extending into higher elevations around Mount Hood by mid to late summer. Winter and early spring are ideal for lower-elevation forest and waterfall hikes, especially in Forest Park, Tryon Creek, and the Columbia River Gorge, though trails can be muddy and slippery. Always check weather forecasts, snow levels, and any posted advisories or closures before heading out, as heavy rain, windstorms, or wildfire activity can temporarily impact trail safety and accessibility.

Confirm current conditions by consulting multiple official and community sources before your hike. Review the websites of managing agencies such as the U.S. Forest Service for the Columbia River Gorge and Mount Hood National Forest, and Portland Parks & Recreation for city and regional parks. Many sites maintain up-to-date alerts on closures, storm damage, wildfire impacts, and seasonal restrictions. Complement this information with recent trip reports from hiking communities and apps, focusing on posts from the last few days or weeks. If road access is required, verify the status of forest and mountain roads, and be prepared with alternate trail options in case of unexpected closures or unsafe conditions upon arrival.

Prioritize trails that align with your fitness, navigation skills, and comfort with exposure. Review elevation profiles and surface descriptions to understand how steep, rocky, or narrow sections may affect your group. Check for hazards common to the region, such as slippery mud, steep drop-offs, fast-moving water near waterfalls, and potential rockfall in the Columbia River Gorge. Bring appropriate gear for rapidly changing Pacific Northwest weather, including layers, rain protection, and footwear with good traction. Carry a map or offline navigation tool and tell someone your route and expected return time. Observe any posted rules regarding pets, seasonal closures, and protected areas to minimize both personal risk and environmental impact.