Four Fall Trips Highly Recommended by Travels with Harley


Fall is the perfect time for a ride and Jim and I have had our fair share of Travels with Harley during autumn. There is nothing better than jumping on the Road King and seeing the leaves change to beautiful hues of gold, burnt umber, orange, red, and vibrant yellow. I was doing some research and discovered some great Travels with Harley rides during the fall.

Grafton, IL

According to USA Today, fall is one of the best times for a Travels with Harley and recommends these great trips on the back of a two-wheeled vehicle.

Lenox, Massachusetts to Stowe, Vermont starts in the Berkshires before taking the riders through some of the most spectacular colors in the US. What is really great about this trip is that the road takes you through the woods on State Highway 100 on to the Green Mountains, which are located in Vermont.


Most people don’t consider a ride from Miami Beach to Key West if they want to see the colors of Autumn, but truth be told, it is beautiful as the route takes you through two of America’s most intriguing cities. When you ride on the Seven Mile Bridge near Marathon, Florida, it is almost like you are riding on top of the water. You may not see the changing of the leaves, but the gorgeous Caribbean blue sea is well worth the trip.


Jim and I have traveled through the Ozarks before, but the trip from Hot Springs to Eureka Springs Arkansas is diverse and pretty amazing. The thermal baths at the hot springs topped off by the mountain roads on scenic Highway 7 is something that should not be missed. The great little towns along the way have some incredible restaurants, diners, and dives and should be on your bucket list.


Door County in Wisconsin has incredible views. With 300 miles of shoreline bordered by Green Bay to the west and Lake Michigan to the east, you will find century old lighthouses, five state parks and amazing apple and cherry orchards. The awesome roadside fruit stands are brimming with fall produce not to mention the brilliant colors of fall from the sumac, oak, birch and maple trees.