Half of this loop route is on the Natchez Trace Parkway from milepost 391 (intersection with US 412) to milepost 416 (intersection with TN Hwy 7) while the other half travels on lightly traveled country roads through the rural communities of Fly, Water Valley, Williamsport and Hampshire. The mid-section of the route crosses the untamed Duck River twice.

Drivers, motorcyclists and bicyclists will all enjoy the 58-mile-long route. Scenery in every direction around the entire route is nothing short of beautiful and is breath-taking at many locations. The route includes some small hills, a few large hills and also travels atop bluffs overlooking the Duck River Valley. On the 25 mile Natchez Trace section of the route you will see five of our Top 30 Natchez Trace sites!

Photo Gallery of the "off Trace" section of the loop.

Photo Gallery of the "Natchez Trace" section of the loop.

Food, Water, Restrooms

There are two markets available - Williamsport Market & Deli half a mile off the loop at mile 9.5 and Duck River Country Store a mile off the loop at mile 49.0. On the Natchez Trace Parkway there are two restroom stops (Jackson Falls and Gordon House).


There are two B&Bs (Creekview Farm Retreat and Fall Hollow) located on the loop. Bicyclists can bike the loop either in one day or, by staying at one of the B&Bs, in two days. Camping is available at Fall Hollow B&B/Campground and on the Natchez Trace for bicyclists only near the TN 50 intersection and five miles south of the southern end of the loop at the Meriwether Lewis park area (tent and RV camping).


Directions for the route are listed below starting at the north end of the loop and first going south on the "off Trace" country roads half of the route in a "clockwise" direction. You can start anywhere on the loop but we would advise going "clockwise" to make the directions easier to follow. You can also view the route on MapMyRide.com.

Directions Cumulative Miles
Starting at Fly's General Store, 5661 Leipers Creek Road, Santa Fe, TN 0.0
Travel north on TN-7 for 0.5 miles to Leiper's Creek Road and turn left, heading south. 0.5
Travel south on Leiper's Creek Road. After 1.9 miles Creekview Farm Retreat B&B will be on the right. After a total of 3.5 miles you will arrive in the Water Valley community. 4.0
Turn right at the "T" intersection to stay on Leiper's Creek Road. Go half a mile. 4.5
Turn left to stay on Leiper's Creek Road. Travel 3.5 miles to the end of Leiper's Creek Road. 8.0
Turn right onto Snow Creek Road/TN 247 and go west 1.4 miles to TN 50/Williamsport Pike. 9.4

Turn right onto TN 50/Williamsport Pike and travel west .1 miles and turn left onto Greenfield Bend Road.

Optional off route side trip: turn left and travel .5 miles across the Duck River to Williamsport Market and Deli.

Travel west and south on Greenfield Bend Road for 4.6 miles where the road changes names to Kettle Mills Road. 14.1
After .5 miles on Kettle Mills Road you will cross the Duck River. 14.6
Continue on Kettle Mills Road for another 1.9 miles to the top of a hill where there are three roads. She Boss to the right, Old Kettle Mills to the left and Love Branch straight ahead. Take the center road onto Love Branch. 16.5
Travel 2.4 miles to Stephenson Schoolhouse Road. Bear right onto Stephenson Schoolhouse. 18.9
After 1.9 miles there is a one lane bridge. On the other side of the bridge turn right onto Cathey's Creek Road. 20.8
After 1.0 miles Cathey's Creek Road turns right and goes over a bridge. If you miss this turn and stay straight you will be on Dry Creek Road. 21.8

Continue another 6.2 miles to where Cathey's Creek Road ends at Ridgetop Road.

Optional off route side trip: after 1.5 miles turn right onto Keg Springs Road and travel one mile to Keg Springs Winery.


Turn right onto Ridgetop Road and travel 2.2 miles to US 412.

Optional off route side trip: turn left onto Ridgetop Road and travel .5 miles to Amber Falls Winery.


Turn right onto US 412 going west towards Hohenwald, TN. Travel 2.4 miles to the Natchez Trace Parkway.

Fall Hollow B&B and Campground is located at the intersection of US 412 and the Natchez Trace Parkway.


Travel north on the Natchez Trace Parkway. After 16.4 miles the parkway will intersect with TN 50. Along this section of the Trace the most popular stops include Fall Hollow Waterfall, Tobacco Farm and Old Trace Drive, Jackson Falls, Baker Bluff Overlook and Gordon House/Duck River.

Optional off route side trip: travel west on TN 50 1.0 miles to the Duck River Country Store.

Continue north on the Natchez Trace Parkway for 7.9 miles to the intersection with TN 7. Along this section of the Trace you will pass by Water Valley Overlook where you can see where you biked earlier in the route! 56.9
Exit the parkway onto TN 7 and turn left heading southeast for 1.3 miles back to your starting point. 58.2

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