35 Miles / 2300 Feet of Climbing
Challenge yourself on rolling terrain that will take you through hilly farmland and backwoods hollows before delivering you to a hilltop winery with panoramic mountain views!
Potential Route Modifications: There are multiple ways to shorten this route. Turning left on Acorn Gap Road (instead of right on Kincaid Road) just before mile 8 will shave off a little over 4 miles from the route. Continuing straight on Hiwassee Road at mile 18.9 instead of turning right onto Anderson Road will reduce the route by 3 miles. Skipping the winery and heading straight to Thompson Road via Old Christenburg Road and the shoulder of Hwy 68 (around mile 28) will reduce the route by 3 miles.
This route starts off as a survey of beautiful farmland before turning into a journey through backwoods hollows and finishing with panoramic vistas from a winery. While these three parts are very different in nature, they all share one common characteristic - hills! The rewards are well worth the effort, but be prepared to do some climbing before taking this one on!
Downtown Madisonville has plenty of free parking, so we recommend starting from downtown, which positions you perfectly for a post-ride recovery meal at one of the many restaurants downtown. (If you plan to celebrate your ride with more than a sampling of wine, you might consider starting & finishing at Tsali Notch Vineyard. Just be advised that they don't have food available, so you'll need to pack your own picnic for after the ride. They have plenty of picnic tables available for just that purpose.)
Head east out of downtown on Main Street and take a left on Houston Street which turns into Old Cemetery Road. Although you'll only be on it for little more than a mile, it will give you a good taste of the hilly conditions you'll find on this ride! When you reach Oak Grove Road/Co Rd 337, go straight across as if you're going to Madisonville Middle School. Veer to the right past the school and then exit the school grounds with a left onto Green Road, which will take you up a little climb before dropping you down a steep straight descent that unfortunately ends abruptly at a stop sign.
At the stop sign, turn right onto Dyer Road and slog your way up the half-mile climb to Oak Grove Road/Co Rd 337. Oak Grove Road will have some traffic, so use caution turning onto it and ride single file. While it's impossible to avoid riding on it altogether, we've limited your time on this road to two short stretches. After turning left onto Oak Grove, you'll be on it for less than a mile before turning right onto Fagin Lane.
Fagin Lane will take you downhill, but watch your speed as you'll need to make a hard left after half a mile onto Fagin Road. Fagin Road may not be marked, but you'll know to turn since it's the first opportunity to take a left, and it's at a sharp bend in the road. Fagin Road is a nice little country lane with a few ups and downs and some nice tree cover.
After a little over a mile on Fagin Road, turn left on King Road. As before, this road may not be marked and the intersection is at a downhill bend in the road. But also as before, it's your first opportunity to turn left so you can be confident that it's the appropriate place to turn.
Over the course of a mile, King Road will climb back up to Oak Grove Road, where you'll turn right. Less than a mile later, you'll be done with Oak Grove Road for good as you turn off of it onto Kincaid Road. Kincaid Road offers some nice views of the southern Blue Ridge Mountains in the distance, and even the Smoky Mountains on a clear day. It also gives you a fun descent! Just don't get too carried away with the roller coaster as you'll need to take a left on Lakeside Road, which once again is your first opportunity to turn left.
Despite its name, Lakeside Road won't take you by any lakes. Instead it takes you through gorgeous farmland with some nice views. It will also give you three climbs, each bigger than the last. Such is the nature of this ride!
At the top of the third climb you'll come to an intersection with Summit Road, where you'll turn left and roll down half a mile before turning right onto Old Loudon Road. In another half-mile, you'll come to Oak Grove Road, where you'll go straight across and stay on Old Loudon Road as it rolls along through farm country for the next couple of miles before finishing with a fast descent down to a nicely paved and clearly more traveled road called Cold Stream Farm Road.
Take a left and brace yourself for a long climb! As the name indicates, the road will take you past Cold Stream Farm, which is a pretty massive operation. Once you crest the climb and start to roll down the other side, look to your right for Hudgins Mill Road.
Hudgins Mill Road will take you past some large-acreage residences before coming to a "T" intersection with Short Bark Road where you'll turn right. Unlike most of the riding you will have done up to this point, Short Bark Road, actually has some curves to it, which, combined with a little downhill, makes for a fun change of pace. You'll also see more trees than farmland.
Short Bark Road comes to a "T" intersection with Hiwassee Road, which offers considerably smoother pavement compared to the bumpy road you were just on, along with the potential for faster-moving traffic. So use caution. After turning right on Hiwassee Road you'll travel a little over half a mile before turning right onto Anderson Road.
The first mile of Anderson Road is more beautiful farmland, but then the scenery shifts to woods as you bend around into a legitimate "hollow" that will have you feeling well-removed from civilization!
Anderson Road is a actually a loop that bends its way back around to Hiwassee Road where you'll turn right on Hiwassee Road and then immediately turn left onto Red Ankle Road, which will most likely be unmarked. You'll know you're on the right road because the pavement will be bumpy and will take you into another wooded hollow (as opposed to heading up the hill on the smooth pavement of Hiwassee Road).
Despite the rough pavement, Red Ankle Road is a real treat offering a completely different experience than the first half of the ride as you work your way through the tree tunnel until reaching a "T" intersection with Brummer Road (which will probably be unmarked as well).
Turn right on Brummer Road and follow it a mile until you reach Old Hwy 68. Go straight across Old Hwy 68 and the road changes names to Craighead Road. Both Craighead Road and Brummer Road offer a nice mix of wooded and pastoral settings, along with a few challenging climbs.
Craighead Road finishes with a nice downhill and bottom outs in a small residential area (watch for dogs), which is your cue to look to the right for a turn onto Old Christenburg Road. After turning right onto Old Christenburg immediately take your first left up a short steep ramp to Hwy 68.
Hwy 68 is a major roadway and you will definitely need to ride on the shoulder. Because the road turns uphill to your right, it has an extra lane on the right side, which virtually eliminates the shoulder on that side. So go straight across Hwy 68 and then go uphill on the shoulder. It will feel awkward to be going against traffic, but the shoulder is wide and you can stay well away from traffic.
After about a quarter mile, you'll turn left onto Pumpkin Hollow Road and leave the highway behind. Pumpkin Hollow Road is a quiet shady road, but it has a pretty challenging half-mile climb that gets steeper as you go! Once on the other side, you'll enjoy a nice fast downhill. As you bottom out and start to go uphill again, take a right on Harrison Road. There should be a sign there pointing to Tsali Notch Vineyard.
A little over a quarter mile and you'll see the entrance to Tsali Notch Vineyard on our right. Follow the road past the field of vines until you get to the gravel driveway leading up to the tasting room. Because of the gravel you may opt to walk your bike in the grass.
At the top of the hill you'll find a cute little tasting room cabin, an event space, a fire pit and picnic tables - plus an amazing view of the Southern Blue Ridge Mountains in the distance beyond the field of vines. It's definitely a photo-worthy view!
At this point, you're little more than 5 miles from the end of the ride, so feel free to take some time for a tasting. The vineyard specializes in muscadine grapes, which are unique to the southeastern United States and have a flavor unlike typical wines. The tasting gives you a wide variety of types which is especially fun if you've never tried muscadine wine before.
After getting your fill of the winery, retrace your steps back to where you turned off of Pumpkin Hollow Road and veer to the right which will have you on Liberality Road. Liberality Road is a roller coaster of a road that starts off with a nice descent and a great view of the mountains in the distance.
After a little over a mile, Liberality Road will bring you back to Hwy 68 where you'll simply go straight across. (No riding on the shoulder this time!) The name changes to Thompson Road on the other side of the highway, and unfortunately it takes you uphill on a short but steep climb. A mile after crossing the highway, take your first right off of Thompson Road onto Lake Road.
Continue on Lake Road through the intersection with Hillcrest Road and past the "lake" (more like a pond) on your left. This will take you down to a "T" intersection with Toomey Road where you'll turn left. Toomey Road has a more residential feel (a sign that you're returning to civilization) and will give you one last challenging hill before dropping you down to Warren Street.
Warren Street has the potential to have some traffic, so use caution as you turn left onto it. Less than half a mile later, veer left onto Main Street, which will take you straight into downtown Madisonville and your post-ride meal!