The Stevenson - Sewanee Lunch Loop travels roughly 40 miles up to the college/mountain town of Sewanee and 30 miles back down to Stevenson.
Restaurants in Sewanee:
931-598-5434 The Blue Chair Bakery & Coffee Shop
931-598-5774 Shenanigan's
931-598-5000 Mountain Breeze Ice Cream Cafe
931-598-9880 Crust Pizza
Lake Cheston in Sewanee is a worthwhile 2-mile side trip in the summer.
Directions to start:
The ride starts at the Stevenson Middle School located in the small town of Stevenson, Alabama.

From Huntsville, Stevenson is about an hour's drive East on US-72. To exit from US-72 near Stevenson, bear right on the ramp off the highway and turn Left/North onto AL-117. The school is located one mile north, on the left. The school is large and hard to miss, with parking in front.

Miles Turn  Description Leg
0.0 Northwest  from Stevenson Middle School on AL-117 / Kentucky Ave 0.2
0.2 Right  on E 2nd Street 1.6
1.8 Left  on CR-75 5.0
6.8 Left  on Rocky Springs Road / CR-74 3.5
10.3 Continue  Rocky Springs Road becomes AL-2 / CR-74 1.0
11.3 Continue  AL-2 / CR-74 becomes TN-27 / S Cedar Ave at the Tennessee state line 2.3
13.6 Left  on 2nd Street 0.6
14.2 Continue  2nd Street becomes TN-156
Climb 1066' in 2.3 miles, 8.8% average grade
23.2
37.4 Bear Left  on Airport Road 0.6
38.0 Left  on Bike path along US-41 1.2
39.2 Rest Stop  in Sewanee (several options) -
  

Side trip to Lake Cheston

Miles Turn  Description Leg
0.0 North  on University Avenue 0.9
0.9 Left  Texas Avenue 0.4
1.3 Bear Right  on Breakfield Road 0.2
1.5 Left  Crosby Lane 0.3
1.8 Arrive  at Lake Cheston -

Return

Miles Turn  Description Leg
39.2 Southwest  on US-41 0.5
39.7 Left  on Sherwood Road / TN-56 3.6
43.3 Begin descent  1123' in 4.8 miles, 4.4% avg grade 12.8
56.1 Continue  on AL-117 into Alabama 12.0
68.1 Right  on AL-117 / Kentucky Ave 0.4
68.5 Finish  at Stevenson Middle School -