Meet your guides in Knoxville this morning. A quick transfer takes us to our friend Alex’s farm in the rolling hills east of the city. Here, we’ll get fitted to our bikes and begin riding through Jefferson County’s verdant farmland. Bike along the banks of the Holston River, then loop back to Alex’s farm for a homegrown lunch. After, transfer into the Smoky Mountains and arrive at Blackberry Farm, the Relais & Châteaux resort that will be the center of our trip. Kick things off with a welcome cocktail, then enjoy dinner at Blackberry Farm’s rugged-yet-refined restaurant.

Accomplished: 21 miles / 34 km, elevation gain: 1,309 feet / 399 meters

Longer Option: 31 miles / 50 km, elevation gain: 2,132 feet / 650 meters

Lunch, Dinner, Snack Enjoy breakfast in the peace of the mountain surrounds, then hop on the bike and head into the valley. As we ride through the foothills, the names of the towns are a reminder of the Cherokee people who once called this land home, but were forced to leave along the Trail of Tears. At a local museum and general store, we’ll get to know the owners and have a quick bite over some local lore. Ride back to Blackberry Farm for a full lunch spread, then spend the afternoon however you like: perhaps at the property’s sumptuous spa or sipping farm ales brewed by Blackberry Farm Brewery. Just before dinner, we’ll regroup for a tasting tour of the Farm’s gardens—a sneak preview of the ingredients that will make a starring appearance on tonight’s dinner plates.

Accomplished: 32 miles / 52 km, elevation gain: 2,063 feet / 629 meters

Shorter Option: 25 miles / 41 km, elevation gain: 1,548 feet / 472 meters

Today’s ride is a knockout that takes us around the entire mountain range north of Blackberry Farm. We’ll follow a narrow ribbon of pavement beside a babbling mountain stream, then cruise on traffic-free roads past farmlands and pastures. Pop into a country store to refuel before looping around the far end of the mountains. We’ll share a picnic lunch in the most perfect rural setting, then transfer back to the hotel if you’re beat—or complete the loop and revel in an epic day of riding. Our final dinner is a fond farewell to the exquisite culinary creations that Blackberry Farm has coined “Foothills Cuisine.”

Accomplished: 36 miles / 60 km, elevation gain: 2,538 feet / 774 meters

Longer Option: 47 miles / 76 km, elevation gain: 3,342 feet / 1,019 meters

There’s time this morning for one more ride along the banks of the Little River to Townsend. Stop for a coffee or step into a dulcimer shop to learn about this instrument’s deep roots in the musical traditions of the Great Smoky Mountains—Dolly Parton famously plays it. Finish with a little push up to the mountain meadows of Tuckaleechee before heading back to Blackberry Farm. After one last lunch, we’ll say our farewells and take you back to Knoxville.

Accomplished: 26 miles / 42 km, elevation gain: 1,496 feet / 456 meters

Longer Option: 32 miles / 51 km, elevation gain: 2,027 feet / 618 meters