North Loop Over-Nighter

Middlesboro, KY

This ride will take you West and North and East. You will visit the Wartburg Visitors Center, Pickett State Park, have lunch at one of my favorite little restaurants, and spend the night in historic Middlesboro.  When you hit the road in the morning, you will make your first photo op at Snake Hollow, and then on to lunch at another great place, Michael’s Diner in Sneedville, TN, and back to Smoky Mountain Harley-Davidson in Maryville.

Day 1

228.9 miles
5 hr 53 min ride time
1 you will ride to the Wartburg Visitors Center for a rest stop. Make sure to sign the log, talk with the ladies, and look around while you are there. They may even have some water for you if you ask nicely.
  • 53.7 miles
  • 1 hr 12 min ride time
2 to Colditz Cove where you park and take the short walk to Northrup Falls. Make sure you have your camera ready.
  • 31.3 miles
  • 44 min of ride time
3 to the Henbos Convenience Store for a snack and to top off the tanks.
  • 6.3 miles
  • 12 min ride time
4 to Pickett State Park. This State Park is a tribute to the Civilian Conservation Corps (CCC) during the Roosevelt era. Take a look around, climb on the natural arch and walk the suspension bridge. Make sure you have your camera ready for this stop!
  • 13.9 miles
  • 22 min ride time
5 continue through the Pickett St Pk up into to Kentucky for lunch at one of my favorite restaurants
  • 29.5 miles
  • 48 min ride time
6 this leg will take you to historic Middlesboro for the evening. There are a number of good places to eat dinner here or you can ride through the tunnel to Cumberland Gap, TN.
  • 93.2 miles
  • 2 hr 35 min ride time


Day 2

159.2 miles
4 hr 57 min ride time
7 you ride up to Cumberland Gap National Park and the Pinnacle Overlook, there are some switchbacks that you will be able to read your own license plate. You will park in Kentucky, walk the short trail to the overlook where you will be in Virginia, and you will be looking at the Cumberland Gap in Virginia and Tennessee. You can also see both ends of the tunnel for the overlook.
  • 5.1 miles
  • 16 min ride time
8 from here you will ride to Snake Hollow, don’t worry about the dogs, they will just greet you a little. Get a picture in front of the sign to show the people back home.
  • 43.7 miles
  • 1 hr 22 min ride time
9 it is just a short ride for lunch at the world-famous Michael’s Dinner. This is where local people go to eat.
  • 6.4 miles
  • 17 min ride time
10 on the last leg, you will ride back to SMH-D on some very nice motorcycle roads with great scenery.
  • 104 miles
  • 3 hr 2 min ride time