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Robin DeanJul 13, 2015CommentShare

Behold our FTC disclosure masterpiece here. Updated Jul 26, 2024, this article contains one or more maps ...

Middlesboro To Etowah: The 411 On 441

Middlesboro, Kentucky is a great town to wake up in, especially if you've picked the right hotel. While packing the bike, it's easy to pause and enjoy the surrounding view. Knowing what's on the docket for today's route, however, makes us want to get going.

Not fifteen minutes into our ride, the environment becomes rural and secluded again. Margaret sees something posturing along the hillside near a local ranch. A wildcat is stalking its game. The tail alone tells us everything we need to know. We're likely looking at a cougar all the way up toward the Kentucky/Tennessee border! It's an impressive animal, for sure. Word is they're making a comeback.

“Crossing into Tennessee, we meander a number of beautiful roads and scenic parkways complete with a short, linear tour of downtown Gatlinburg.”

Crossing into Tennessee, we meander a number of beautiful roads and scenic parkways complete with a short, linear tour of downtown Gatlinburg. 32 picks up 33, 33 junctions with 61, 61 meets 1, 139 onto 66, 35, 449 ... they're all nice. It's when we reach the 441/321/Gatlinburg bypass combo that today's route is cracked wide open.

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This cuts through the Smokey Mountains, a first for Margaret. Even the (minimal) expressway time is beautiful from a sightseer's perspective, full of twists and hills. Continuing along, the roads become more and more isolated until we enter the national park.

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Being as how it's Memorial Day weekend, 441 has its fair share of traffic. Leaving enough distance to avoid stop-and-go riding minimizes the required effort to keep things running smooth. At first, the congestion is frustrating but then we find out why.

Fog! They don't call them the Smokey Mountains for nothin'. Riding slow, there's no harm in pretending your head's in the clouds. What's more, there are a good many pull-offs where you can stop to look out over the range. "Chimney Tops" is too crowded today, so we roll on to Cherokee.

Cherokee Ice Cream
Cherokee Restaurant

In Cherokee, we're immediately faced with a number of lunch options. What's more important is the ice cream that we'll most certainly demolish afterwards. Sassy Sunflowers Bakery & Café provides the exact atmosphere and menu we're after for the intermission. It's healthy, for one but don't stare at the baked goods for too long or you might not escape another purchase. Even if you do escape said trap, you won't get around Little Princess ice cream shop.

Today's ride is winding down. I know, because my wife has begun referring to every fly she encounters as Jeff Goldbloom. I'm talkin' full blown conversations, folks.

Once we arrive at my parent's house, we're greeted with barbecue, banter and bedding ... an excellent conclusion to our southbound effort.

Ready for more? Day Five: Etowah to Meadows of Dan

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What's Your Favorite Sport Touring Motorcycle Route From Middlesboro To Etowah?

There are many twisty, scenic travel options connecting the two. Which roads do you prefer and why? Where do you like to stop along the way? Your input is invited. Leave a comment and/or write an article!

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Robin Dean

About Robin Dean

Motorcycle advocate, enthusiast and traveler. Founder, The Riding Obsession (2014). MSF RiderCoach credentials: "loosely regarded adult supervisor, probably good enough for rock 'n' roll" ~ Tidal Playlist

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