Bethany:
Fort Wilderness will be in its prime in the fall when you visit. I can smell the pine as I type!
There's rarely a wait, especially if you have Advanced Dining Reservations, at Trail's End. Because it's not located in the same vicinity as Chip 'n' Dale's campfire singalong, I'd recommend making your reservation for somewhere around 6:00 p.m. This will give you ample time to enjoy the buffet and then mosey over to the amphitheatre for the show.
You should be visiting while it's still Daylight Savings Time, so the fire pots will be lit at 7:40 p.m. and the show begins at 8 p.m. The walk is a good 15-minute stroll, but it's flat and probably best to walk off all the yummy dinner! If you don't feel like walking, you can always catch a bus at the Pioneer Hall bus stop (just ask your server to point you in the general direction, you can't miss it) to the Meadows bus stop. You'll still have a little bit of a walk, but you can break it up with a stop inside the trading post.
The fireworks at Magic Kingdom aren't
scheduled to go off until 10 p.m. on October 15, so you may either want to consider watching the movie that will begin around 8:40 after the sing-a-long or take your time walking to the pier for the Electric Water Pageant around 9:30ish and then the fireworks!
Wishing y'all a magical vacation!
Whitney