Middleton Loop

Middleton, TN, US

Route Overview

21 mi.
1,078 ft.

The Middleton Loop is a fun little ride on some curvy low-traffic backroads through Southwest Tennessee's agricultural landscape. A few wooded climbs and descents will be rewarded by a post-ride meal in Middleton, Tenn.

Route Details

Potential Route Modifications: Turning right off of Upton Road onto Norton Road at mile 8.4 and skipping the New Hope/Smalley loop reduced the route by nine miles. The route can be ridden in either direction, and you’ll want to sort out your timing and direction to avoid passing by Middleton High School at peak drop-off and pick-up times.

Getting Started:

Beginning from downtown Middleton, Tenn., where the inviting Green Frog Coffee & Grill awaits, we've carefully mapped the ride with a meal in mind. There are free parking options downtown on Dogwood Avenue or at the spacious lot on Beaver Road, just across Hwy 125 (Main Street).

From downtown Middleton, carefully turn left onto Main Street and head south across the train tracks and then turn right onto Florida Street. Florida Street will take you past the Middleton High School before coming to an intersection with Roosevelt Road, where you’ll turn right. Shortly after turning onto Roosevelt, the road will bend to the left and become Bishop Road. In addition to the name change, the scenery will change as well, as you leave the residential area and head into a more rural landscape.

Bishop Road parallels the train tracks for about three quarters of a mile before it curves to the right and crosses the tracks. Don’t continue straight or you’ll end up on Old Enon Road. After crossing the tracks, you’ll be treated to a really pleasant landscape with farmland on your left and trees on your right. Be prepared for this part of this stretch as the pavement is a little rough.

After a couple of miles, you’ll leave the farmland behind and head into the trees and up a hill. The climb is not terribly steep, but you will feel it as you plod along for over a mile before the road starts to level out again.

Just as you start to crest the climb, you’ll take a sharp right turn onto Ferrell Road. Ferrell is a fun road that runs along a ridgeline. It’s tree-lined for the most part, especially at the start, so you don’t have a lot of views, but you can tell that you’re riding a ridge as the topography drops away on both sides. The only downside to the road is the pavement quality, which goes from bad to worse, so you’ll need to keep your speed in check to keep the vibrations to a minimum and watch your lines carefully to avoid potholes.

After winding around for three miles, Ferrell intersects with George West Road and you’ll turn right, which will feel more like a righthand bend in the road than an actual turn. There is an option to turn left on George West, but it’s a dirt road in that direction. George West continues through the trees on bumpy pavement for another half-mile before merging with Bowden Lane, which again will feel like a continuation of the same road).

Almost immediately after this merger, veer to the left onto Upton Road and then stay left a quarter mile later when the road splits to continue on Upton Road. It winds along – with noticeably better pavement – for a little less than two miles before dropping out of the woods on a short descent and into a residential neighborhood.

As the road bottoms out from the descent, you’ll come to a stop sign at New Hope Road. Go straight onto New Hope, which has even smoother pavement, and follow it as it bends to the left and starts to head uphill. After a mile, turn left onto Smalley Road and continue with the gradual climb.

Smalley feels residential at first but then it transitions into pure woods, which makes it a fun little loop. After close to two miles, Smalley brings you back to New Hope Road where you’ll turn right and enjoy a fun mile-long downhill before hitting a short rise coming up from Dry Branch. After making it over the rise, the downhill fun continues as you work your way back to Upton Road.

New Hope Road bends hard to the left at this intersection, but you’ll simply go straight to head back onto Upton Road. Upton will take you back into the woods with a short but tough climb, and a little over a mile later will bring you to a split where you’ll veer left off of Upton and onto Norton Road.

Norton makes for a great finish as it brings you back to town on a scenic three-mile downhill stretch (except for a short rise coming up from Porters Creek). Just before you reach Hwy 125, turn right onto a very narrow little road called Reindeer Street, which becomes Bluebird Avenue on its way to bringing you back to Hwy 125. Carefully turn left onto Hwy 125, cross the railroad tracks, and then turn right onto Dogwood Avenue, which will bring you back to your car and most importantly to your post-ride meal at the Green Frog.

Important Reminders

Bike TN routes often include roads with car and truck traffic. Although the Bikeways are routed on low-traffic and low-speed roads whenever possible, most are designated for cyclists who are comfortable riding in some amount of traffic.

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