The total elevation difference for Roosevelt Way is 2,210 feet which is about average. Sometimes this great outdoors trail gets really dry, so donít forget to check for any current fire restrictions before you go. This is not a very long great outdoors trail but it's always splendid to bring some emergency supplies, you never know what could happen. This is a one trailhead hiking and backpacking trail, so you'll be trekking it in and back out. This walk shouldn't take more than 5 hours, but you never know stuff could go wrong and you could get stuck so be prepared for that. Roosevelt Way is 5.4 miles long it's an average length backpacking trail. This backpacking trail goes through some very different elevations, and that means that some parts of the backpacking trail could be very different from other parts of it.