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Tennessee Hills and Stills

Duration
6 nights
BASE PRICE
From $2,579
LEVEL OF DIFFICULTY
Active
Book Tour
type
Supported
DISTANCE
25-37 miles per day

Overview

Few names are as synonymous with Tennessee as Jack Daniel’s. And few parts of the South are as scenic as the landscapes you’ll enjoy on this ride.

From Jack Daniel’s in Lynchburg to George Dickel in Normandy to Nearest Green in Shelbyville, you’ll enjoy slow travel, true southern charm, delicious southern meals, and a landscape rich in culture and natural beauty. 

As you stop in towns–many little more than hamlets–the local folk will welcome you with Southern hospitality and, when you leave, wish you a warm and hearty “Y’all come back!” And they’ll mean it.    

At each day’s end, gracious innkeepers will welcome you home, eager to share your lodging’s rich history. 

For much of the ride, you’ll see a Tennessee that looks much as it did in the late 18th century, when Scottish and Irish immigrants made their way west. Rolling hills draped with forests. Farms sprawling across the flatlands. Brooks and streams filtered by limestone ledges and often overflowing their banks, bringing fresh nutrients to the farmlands. Conditions perfect for settlers who brought with them the distilling practices of their homelands.

Barely a century ago, Tennessee had hundreds of distilleries–most on farms but many of a more “informal” type hidden in the dense forest. (And oh, the stories these backroads could tell!) This ended with Prohibition, and only two whiskey producers–Jack Daniel’s and George Dickel–survived the period. In recent years, thanks to changes in Tennessee law, many smaller distillers have emerged to continue the Tennessee whiskey tradition. And to offer tours and samples to eager visitors.

One of our favorites: Prichard’s Distillery in Kelso, where the family tradition extends back five generations to the 1820s, when Benjamin Prichard passed along his tubs, utensils, still and–most important–his techniques to his son Enoch. Another favorite: Nearest Green Distillery, named for Nathan Green, a former slave credited with teaching Jack Daniel how to make whiskey. If you’re lucky, you may meet Victoria Eady Butler, Green’s great-great-granddaughter and the first female African-American master blender in history.

Highlights

Tours and tastings at four of the finest craft distilleries in South Central Tennessee, home to Jack Daniel's and George Dickel.

Southern hospitality at family owned Bed and Breakfasts

True southern meal at Miss Mary Bobo's

Riding through a landscape rich in history and natural beauty

Tennessee Walking Horse Capital of the world

Difficulty

Rolling hills, paved roads, rural landscape

Itinerary

Scheduled Tours:

Day 1: Arrive in Shelbyville (0 miles)

Arrive in Shelbyville, located 50 miles southeast of Nashville. Rich in both cultural history and natural beauty, the town is known worldwide for the annual Tennessee Walking Horse National Celebration, a prestigious equestrian event dating back to 1939. It’s located along the Duck River in southern Middle Tennessee, where you can choose to fish or float, enjoy a long bike ride through the scenic countryside, ride a horse, enjoy one of their numerous festivals, or explore the beautiful historic downtown. Enjoy dinner on your own in town. 

Lodging: Cinnamon Ridge B&B, a two-story colonial-style house situated in the heart of Tennessee Horse country

Cinnamon Ridge B&B

Day 2: Shelbyville-Bell Buckle-Nearest Green (35 miles)

Enjoy a loop ride from Shelbyville to historic Bell Buckle, a little town with big charm. You’ll find the epitome of “southern charm” here with antique stores, an old fashioned ice cream parlor, southern diner and coffee shop. You’ll have time to enjoy lunch at the Bell Buckle Cafe or Coffee Shop and Book Swap and visit/shop the antique stores before continuing on to the Nearest Green Distillery (tours on weekends only), where, if you’re lucky, you may meet Victoria Eady Butler, Nearest Green’s great-great-granddaughter and the first female African-American master blender in history.

Lodging: Cinnamon Ridge B&B

Day 3: Shelbyville-Wartrace-Cascade Hollow (35 miles)

Today you venture through Cascade Hollow towards the home of George Dickel Whiskey at the Cascade Hollow Distillery. After a tour and tasting, you can enjoy a picnic lunch by the creek before making your way on back roads to Shelbyville. You’ll also pass through Wartrace, home to the Tennessee Walking Horse National Museum

 Lodging: Cinnamon Ridge B&B

 

Day 4 Shelbyville-Lynchburg (25 miles)

Pedal your way through the Tennessee highlands towards Lynchburg, home to the famous Jack Daniel’s Distillery. Enjoy a true southern meal at Miss Mary Bobo’s followed by a distillery tour and tasting at Jack Daniel’s. Overnight accommodations are one mile from downtown, where you can explore shops, a winery, and restaurants on your own. 

Lodging: Tolley House B&B, a Greek Revival home and one of historic Lynchburg’s oldest antebellum homes

Tolley House B&B

 

Day 5: Lynchburg-Kelso-Lynchburg (37 miles)

Ride through rolling back-hills roads into deep Tennessee farm country to Prichard's Distillery, which opened in an old schoolhouse in Kelso in 1997 and was the first new legal distillery to open in the state since the repeal of Prohibition. You can also enjoy rums that come from American molasses sourced from Louisiana as well as a variety of liqueurs. 

Tip 1: Taste Prichard's Double Chocolate Flavored Whiskey, which blends bourbon with artisan chocolate, or Lincoln County Lightning, which was rated by Southern Living as the "#2 Legal Moonshine in the U.S."

Lodging: Tolley House B&B

Jack Daniel's Distillery Entrance

Day 6: Lynchburg Loop - Lynchburg Distillery and Winery (25-47 miles) Opt for a loop ride of your choice ranging from 20-47 miles. Experience one or two distilleries. The longer range will take you to Branch Water Distillery in Winchester, TN. The shorter loop will keep you close to Lynchburg to visit the local Lynchburg Distillery and Winery, not affiliated with Jack Daniel’s. Taste moonshine, wine, vodka, rum and whiskey too at the Lynchburg Winery and Distillery in downtown Lynchburg!

Lodging: Tolley House B&B

Day 7: Departure from Lynchburg - transfer or ride back to Shelbyville. (25 miles)

 

Alternate Daily Program for Private Tours:

Day 1: Shelbyville (0 miles)

Arrive in Shelbyville, located 50 miles southeast of Nashville. Rich in both cultural history and natural beauty, the town is known worldwide for the annual Tennessee Walking Horse National Celebration, a prestigious equestrian event dating back to 1939. It’s located along the Duck River in southern Middle Tennessee, where you can choose to fish or float, enjoy a long bike ride through the scenic countryside, ride a horse, enjoy one of their numerous festivals, or explore the beautiful historic downtown. Enjoy dinner on your own in town. 

Lodging: Cinnamon Ridge B&B, a two-story colonial-style house situated in the heart of Tennessee Horse country

Day 2: Shelbyville to Lynchburg (25 miles)

Pedal your way through the Tennessee highlands towards Lynchburg, home to the famous Jack Daniel’s Distillery. Enjoy a true southern meal at Miss Mary Bobo’s and a distillery tour. Overnight accommodations are one mile from downtown, where you can explore shops, a winery, and restaurants on your own. 

Lodging: Tolley House B&B, a Greek Revival home and one of historic Lynchburg’s oldest antebellum homes,

Tolley House Front Porch

Day 3: Lynchburg-Kelso-Mulberry (25 miles)
Ride through rolling backhills roads into deep Tennessee farm country to Prichard's Distillery, which opened in an old schoolhouse in Kelso in 1997 and was the first new legal distillery to open in the state since the repeal of Prohibition. You can also enjoy rums that come from American molasses sourced from Louisiana as well as a variety of liqueurs. 

Tip 1: Taste Prichard's Double Chocolate Flavored Whiskey, which blends bourbon with artisan chocolate, or Lincoln County Lightning, which was rated by Southern Living as the "#2 Legal Moonshine in the U.S."

Lodging: Mulberry Lavender Farm and B&B, an historic 1860s farmhouse formerly owned by Wiley Daniel, a Civil War hero and brother of Jack. It’s a working farm where horses and sheep outnumber people. The ultimate in farm-to-table dining–and the table’s on the farm!

 Tip 2: Spend an extra night on the farm! Ride, read or count sheep (literally) before napping.

Mullberry Lavender Farm

Day 4: Mulberry to Tullahoma (30 miles)

Ride the open road through rolling hills past Tims Ford Lake into Tullahoma, a small but bustling town that has become a world leader in flight and engineering research. Enjoy coffee shops, breweries, distilleries, restaurants, and numerous lakes and state natural areas.

Lodging: Grand Lux Inn, a fully-remodeled 1905 home. The inn’s magnificent wrap-around porch is great for watching life in the downtown Historic District of Tullahoma.

 

Day 5: Tullahoma to Bell Buckle (23 miles)

Today you venture through Cascade Hollow towards the home of George Dickel Whiskey at the Cascade Hollow Distillery. You can enjoy a picnic lunch by the creek before making your way on back roads to Bell Buckle, a little town with big charm. You’ll find the epitome of “southern charm” here in the main square with antique stores, an old fashioned ice cream parlor, and southern diner and coffee shop all within walking distance of the B&B. 

You’ll also pass through Wartrace, home to the Tennessee Walking Horse National Museum.  

Lodging: Seasons B&B, just steps from the main square, owned and operated by “sisters and best friends” Anita Wade and Marie Pope, who promise to make you feel like family, too.

Bell Buckle Mural

Day 6: Bell Buckle to Shelbyville (22 miles)

On your final day of riding, you’ll visit Nearest Green Distillery (tours on weekends only), where, if you’re lucky, you may meet Victoria Eady Butler, Nearest Green’s great-great-granddaughter and the first female African-American master blender in history.

After a picnic lunch, you make your way back into Shelbyville to complete your Tennessee Still and Hills circuit. 

Day 7: Departure from Shelbyville (0 miles)

Dates & Pricing

Dates:

Scheduled departures: June 3, August 19, September 16, October 21, November 11, 2022 (minimum of 6 participants)

 Daily upon request for groups of 4 or more (subject to availability)

Tennessee Still and Hills is offered daily, on request, subject to availability, to parties of four or more. The itinerary can easily be customized to meet your interests and cycling preferences. It is offered with a support van with driver/bike mechanic, and you can also request a ride-along guide.

The route may be offered in the opposite direction depending on start day to ensure the most open distilleries and restaurants.

Transfers for your party can be arranged from/to Nashville or Chattanooga or other locations.

Pricing:

Scheduled Departures:

$2,597 per person double occupancy

$657 single supplement

$400 e-bike

$250 hybrid bike


Private Departures:

$2,679 per person double occupancy

$607 Single supplement

$400 e-bike

$250 hybrid bike

Van transfers for private groups only: $99 per group roundtrip from Chattanooga, $149 per group roundtrip from Nashville to the starting location.

Inclusions

6 nights lodging

6 breakfasts

3 picnic lunches

Tastings and tours at 4 distilleries

Luggage transfers

Support vehicle with driver/mechanic

GPS files

Map
Gallery

Scheduled Tours:

Day 1: Arrive in Shelbyville (0 miles)

Arrive in Shelbyville, located 50 miles southeast of Nashville. Rich in both cultural history and natural beauty, the town is known worldwide for the annual Tennessee Walking Horse National Celebration, a prestigious equestrian event dating back to 1939. It’s located along the Duck River in southern Middle Tennessee, where you can choose to fish or float, enjoy a long bike ride through the scenic countryside, ride a horse, enjoy one of their numerous festivals, or explore the beautiful historic downtown. Enjoy dinner on your own in town. 

Lodging: Cinnamon Ridge B&B, a two-story colonial-style house situated in the heart of Tennessee Horse country

Cinnamon Ridge B&B

Day 2: Shelbyville-Bell Buckle-Nearest Green (35 miles)

Enjoy a loop ride from Shelbyville to historic Bell Buckle, a little town with big charm. You’ll find the epitome of “southern charm” here with antique stores, an old fashioned ice cream parlor, southern diner and coffee shop. You’ll have time to enjoy lunch at the Bell Buckle Cafe or Coffee Shop and Book Swap and visit/shop the antique stores before continuing on to the Nearest Green Distillery (tours on weekends only), where, if you’re lucky, you may meet Victoria Eady Butler, Nearest Green’s great-great-granddaughter and the first female African-American master blender in history.

Lodging: Cinnamon Ridge B&B

Day 3: Shelbyville-Wartrace-Cascade Hollow (35 miles)

Today you venture through Cascade Hollow towards the home of George Dickel Whiskey at the Cascade Hollow Distillery. After a tour and tasting, you can enjoy a picnic lunch by the creek before making your way on back roads to Shelbyville. You’ll also pass through Wartrace, home to the Tennessee Walking Horse National Museum

 Lodging: Cinnamon Ridge B&B

 

Day 4 Shelbyville-Lynchburg (25 miles)

Pedal your way through the Tennessee highlands towards Lynchburg, home to the famous Jack Daniel’s Distillery. Enjoy a true southern meal at Miss Mary Bobo’s followed by a distillery tour and tasting at Jack Daniel’s. Overnight accommodations are one mile from downtown, where you can explore shops, a winery, and restaurants on your own. 

Lodging: Tolley House B&B, a Greek Revival home and one of historic Lynchburg’s oldest antebellum homes

Tolley House B&B

 

Day 5: Lynchburg-Kelso-Lynchburg (37 miles)

Ride through rolling back-hills roads into deep Tennessee farm country to Prichard's Distillery, which opened in an old schoolhouse in Kelso in 1997 and was the first new legal distillery to open in the state since the repeal of Prohibition. You can also enjoy rums that come from American molasses sourced from Louisiana as well as a variety of liqueurs. 

Tip 1: Taste Prichard's Double Chocolate Flavored Whiskey, which blends bourbon with artisan chocolate, or Lincoln County Lightning, which was rated by Southern Living as the "#2 Legal Moonshine in the U.S."

Lodging: Tolley House B&B

Jack Daniel's Distillery Entrance

Day 6: Lynchburg Loop - Lynchburg Distillery and Winery (25-47 miles) Opt for a loop ride of your choice ranging from 20-47 miles. Experience one or two distilleries. The longer range will take you to Branch Water Distillery in Winchester, TN. The shorter loop will keep you close to Lynchburg to visit the local Lynchburg Distillery and Winery, not affiliated with Jack Daniel’s. Taste moonshine, wine, vodka, rum and whiskey too at the Lynchburg Winery and Distillery in downtown Lynchburg!

Lodging: Tolley House B&B

Day 7: Departure from Lynchburg - transfer or ride back to Shelbyville. (25 miles)

 

Alternate Daily Program for Private Tours:

Day 1: Shelbyville (0 miles)

Arrive in Shelbyville, located 50 miles southeast of Nashville. Rich in both cultural history and natural beauty, the town is known worldwide for the annual Tennessee Walking Horse National Celebration, a prestigious equestrian event dating back to 1939. It’s located along the Duck River in southern Middle Tennessee, where you can choose to fish or float, enjoy a long bike ride through the scenic countryside, ride a horse, enjoy one of their numerous festivals, or explore the beautiful historic downtown. Enjoy dinner on your own in town. 

Lodging: Cinnamon Ridge B&B, a two-story colonial-style house situated in the heart of Tennessee Horse country

Day 2: Shelbyville to Lynchburg (25 miles)

Pedal your way through the Tennessee highlands towards Lynchburg, home to the famous Jack Daniel’s Distillery. Enjoy a true southern meal at Miss Mary Bobo’s and a distillery tour. Overnight accommodations are one mile from downtown, where you can explore shops, a winery, and restaurants on your own. 

Lodging: Tolley House B&B, a Greek Revival home and one of historic Lynchburg’s oldest antebellum homes,

Tolley House Front Porch

Day 3: Lynchburg-Kelso-Mulberry (25 miles)
Ride through rolling backhills roads into deep Tennessee farm country to Prichard's Distillery, which opened in an old schoolhouse in Kelso in 1997 and was the first new legal distillery to open in the state since the repeal of Prohibition. You can also enjoy rums that come from American molasses sourced from Louisiana as well as a variety of liqueurs. 

Tip 1: Taste Prichard's Double Chocolate Flavored Whiskey, which blends bourbon with artisan chocolate, or Lincoln County Lightning, which was rated by Southern Living as the "#2 Legal Moonshine in the U.S."

Lodging: Mulberry Lavender Farm and B&B, an historic 1860s farmhouse formerly owned by Wiley Daniel, a Civil War hero and brother of Jack. It’s a working farm where horses and sheep outnumber people. The ultimate in farm-to-table dining–and the table’s on the farm!

 Tip 2: Spend an extra night on the farm! Ride, read or count sheep (literally) before napping.

Mullberry Lavender Farm

Day 4: Mulberry to Tullahoma (30 miles)

Ride the open road through rolling hills past Tims Ford Lake into Tullahoma, a small but bustling town that has become a world leader in flight and engineering research. Enjoy coffee shops, breweries, distilleries, restaurants, and numerous lakes and state natural areas.

Lodging: Grand Lux Inn, a fully-remodeled 1905 home. The inn’s magnificent wrap-around porch is great for watching life in the downtown Historic District of Tullahoma.

 

Day 5: Tullahoma to Bell Buckle (23 miles)

Today you venture through Cascade Hollow towards the home of George Dickel Whiskey at the Cascade Hollow Distillery. You can enjoy a picnic lunch by the creek before making your way on back roads to Bell Buckle, a little town with big charm. You’ll find the epitome of “southern charm” here in the main square with antique stores, an old fashioned ice cream parlor, and southern diner and coffee shop all within walking distance of the B&B. 

You’ll also pass through Wartrace, home to the Tennessee Walking Horse National Museum.  

Lodging: Seasons B&B, just steps from the main square, owned and operated by “sisters and best friends” Anita Wade and Marie Pope, who promise to make you feel like family, too.

Bell Buckle Mural

Day 6: Bell Buckle to Shelbyville (22 miles)

On your final day of riding, you’ll visit Nearest Green Distillery (tours on weekends only), where, if you’re lucky, you may meet Victoria Eady Butler, Nearest Green’s great-great-granddaughter and the first female African-American master blender in history.

After a picnic lunch, you make your way back into Shelbyville to complete your Tennessee Still and Hills circuit. 

Day 7: Departure from Shelbyville (0 miles)

Tours and tastings at four of the finest craft distilleries in South Central Tennessee, home to Jack Daniel's and George Dickel.

Southern hospitality at family owned Bed and Breakfasts

True southern meal at Miss Mary Bobo's

Riding through a landscape rich in history and natural beauty

Tennessee Walking Horse Capital of the world

Rolling hills, paved roads, rural landscape

Dates:

Scheduled departures: June 3, August 19, September 16, October 21, November 11, 2022 (minimum of 6 participants)

 Daily upon request for groups of 4 or more (subject to availability)

Tennessee Still and Hills is offered daily, on request, subject to availability, to parties of four or more. The itinerary can easily be customized to meet your interests and cycling preferences. It is offered with a support van with driver/bike mechanic, and you can also request a ride-along guide.

The route may be offered in the opposite direction depending on start day to ensure the most open distilleries and restaurants.

Transfers for your party can be arranged from/to Nashville or Chattanooga or other locations.

Pricing:

Scheduled Departures:

$2,597 per person double occupancy

$657 single supplement

$400 e-bike

$250 hybrid bike


Private Departures:

$2,679 per person double occupancy

$607 Single supplement

$400 e-bike

$250 hybrid bike

Van transfers for private groups only: $99 per group roundtrip from Chattanooga, $149 per group roundtrip from Nashville to the starting location.

6 nights lodging

6 breakfasts

3 picnic lunches

Tastings and tours at 4 distilleries

Luggage transfers

Support vehicle with driver/mechanic

GPS files

Maps are for reference only and may not be the actual routes used.
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