This urban Portland hike is unique for combining a trail, a tram, a trolley, and a train in one well-guided loop that offers great views of the city. You can enter the 4T loop at any point but this is a good order of events for first-timers: Hike from the Oregon Zoo (notable for its conservation efforts and gang of endangered species) to Council Crest Park (the highest point in Portland at 1,073 feet), then down to the campus of Oregon Health and Science University (OHSU). Get on Portland Aerial Tram, which will send you gliding 3,000-plus feet downhill along the Willamette River in just a few minutes. Next, step on the trolley (called Portland Streetcar) for a ride downtown and to refuel (we recommend the hot chocolate at Cacao). You can take the train (MAX Light Rail) back to the start of the loop/your car/home base depending on where you’re posted in Portland. Alternately, if you’re staying in a hotel downtown, you can begin the loop with a train ride to the start of the trail. Either way, the entire journey takes around four hours. And it is a really fun tour of Portland for the family, but note that the walking stretch of the 4T is about four miles—so the trail portion is best for kids of a certain leg length.

Photo: Dzung Tran

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