One of my favorite autumn walks is The Rail Trail. My dogs and kids love it too. The gravel path is easy on the knees and on the pads of my dog's feet (seriously). The trail begins at the end of Prospect Street , however, I find that parking at the end of Halpin Lane (by The Barn and the Ridgefield Guild of Artist) is a perfect spot. A short walk through the woods brings you to the trail. It's approximately a 2.25 mile run slightly downhill to the end (at Florida Road). You're looking at a 5 mile, beautiful stretch of terrain.
There are a few areas on the each side of the trail that lead into wooded hiking trails. Florida Refuge is an easy hiking trail and you will come upon it about 1.75 miles into your hike. Another one that I like is Whitbeck Preserve. It is on the south side of the trail at about the 2.3 mile mark. This trail is short (2.3 miles) and very rocky. You may encounter a few little critters...I've seen turtles, snakes and some turkey vultures. It makes the run or walk quite entertaining. See you there.