The Virginia Creeper trail has become one of my favorite “can’t miss” yearly activities that we do. We have always gone in the summer, but I have had friends go year round and their pictures are beautiful. For clarity, when we do the Creeper Trail, we always take the route from White Top Mountain to Damascus Virginia. There are multiple different routes you can take, but this one is a gentle downhill glide the whole way and great for small kids. Don’t let the high number of miles scare you. There is one brief spot at the beginning where you pedal slightly up a small hill and the rest you could almost coast down. Both our second and third sons were 5 years old when they completed the trail on their own bikes. Kids have to pedal a little more because their bikes are so small, but because of the downhill glide they did great. We did bring this bike trailer each of those times in case they didn’t make it the whole way, but we ended up just using it to store our lunch. We have gotten so much use out of that bike trailer. It allowed us to go on so many adventures that we otherwise wouldn’t have gone on when the boys were too small to ride the whole way.