The Jack Trail - Sippin' to Saddles

The Jack Daniel's Distillery in Lynchburg serves as the cornerstone of Tennessee's whiskey legacy. Nestled deep in Moore County, the oldest registered distillery in the United States continues to craft its globally celebrated Tennessee Whiskey using the Charcoal Mellowing process that gives it its distinct smooth flavor. Visitors can join guided tours that trace the whiskey's journey from the cave spring water and grain to the charcoal vats and aging barrel houses, culminating in a tasting experience.

Located in the heart of Nashville, the National Museum of African American Music (NMAAM) serves as a powerful tribute to the profound cultural contribution of African Americans across all music genres. This museum is the only facility dedicated to preserving and celebrating the influence of Black artists, covering over 50 styles from spirituals and the blues to jazz, gospel, and hip-hop. Visitors can engage with highly interactive exhibits that trace music’s journey from African origins to its global impact, making it an essential stop for understanding the foundational rhythms of the Jack Trail's music theme.

The Stones River National Battlefield in Murfreesboro offers a sobering historical detour from the trail's musical and spirit-filled focus. The site of one of the Civil War's bloodiest and most pivotal winter battles, the outcome here ensured the Union maintained control of Middle Tennessee. Visitors can explore the expansive, preserved grounds, drive the battlefield tour route, and reflect at the Stones River National Cemetery, one of the oldest in the nation. This solemn stop provides deep context into the strategic importance of the region during the conflict.

Cannonsburgh Village in Murfreesboro offers a quaint step back in time, presenting a preserved and reconstructed glimpse of 19th-century Tennessee life. This charming, historic village features over 20 authentic buildings moved to the site, including a working gristmill, a one-room schoolhouse, a blacksmith shop, a wedding chapel, and several log homes. It serves as a peaceful, walkable retreat where visitors can explore the rustic, pioneering spirit and architecture that defined the homes and communities of the early Tennessee settlers along the Jack Trail.

The Old Stone Fort State Archeological Park in Manchester preserves one of the most mysterious and historically significant sites in Tennessee. The "fort" is not a defensive structure in the traditional sense, but an ancient, 400-foot-long earthen wall enclosure built by Native Americans between 1,000 and 2,000 years ago. This complex was likely used for ceremonial purposes, not military defense, and its walls incorporate the steep bluffs formed by the Duck and Little Duck Rivers. Visitors can hike the beautiful trails that trace the perimeter of the ancient enclosure and lead to stunning waterfalls, connecting the region's deep Indigenous history with its beautiful natural landscape.

For a refreshing break from the trail’s distilleries and historic sites, Machine Falls in the Short Springs Natural Area near Tullahoma offers a picturesque dose of Middle Tennessee's natural beauty. This multi-tiered waterfall is often cited as one of the prettiest in the region, featuring water cascading over a wide, smooth bedrock face. Visitors can hike a moderate loop trail through the forested landscape to reach the base of the falls, providing a tranquil and rewarding outdoor adventure that showcases the stunning natural diversity of the countryside.

The scenic Tims Ford State Park in Winchester offers a tranquil, expansive water escape on one of the most beautiful reservoirs in the state. Centered on the crystal-clear waters of Tims Ford Lake, the park is a premier destination for fishing, boating, and swimming. Beyond the aquatic recreation, visitors can stay in modern cabins, camp, and play the nationally recognized Bear Trace at Tims Ford 18-hole golf course. This popular stop provides a refreshing contrast to the trail's historical sites, showcasing the spectacular natural landscapes of Middle Tennessee.

The Uncle Nearest Distillery in Shelbyville is a key highlight on the Jack Trail, representing a powerful and essential story in the history of Tennessee Whiskey. The distillery is named in honor of Nathan "Nearest" Green, the formerly enslaved man who taught Jack Daniel the art of distilling. This destination celebrates Nearest's legacy as the first known African American master distiller. Visitors can explore the expansive 270-acre farm, tour the world-class facility, and sample the award-winning whiskeys, which are quickly becoming a global icon in the spirits industry. It’s a meaningful stop that connects the trail’s whiskey theme to a crucial piece of American history.

Arrington Vineyards offers a delightful, scenic experience that complements the whiskey theme of the Jack Trail with a different kind of celebrated spirit. Located just south of Nashville, this vineyard and winery, co-owned by country music star Kix Brooks, sits on rolling hills of historic farmland, providing stunning views of the countryside. Visitors can enjoy wine tastings in the rustic barn, purchase a bottle, and picnic on the grounds while taking in the live music and seasonal events. It's an ideal stop to experience the agricultural beauty and refined hospitality of Middle Tennessee.

Lucky Ladd Farms in Eagleville provides a delightful, family-friendly detour that showcases the agricultural heart of the Jack Trail’s countryside. Known as one of Tennessee's largest petting farms, this agritourism destination offers visitors a chance to engage with the region’s rural heritage through hands-on experiences. Children and adults alike can enjoy a massive petting zoo, pony rides, extensive play areas, and popular seasonal attractions like the towering corn maze and pumpkin patch. It’s an engaging, active stop that highlights the beauty of the Middle Tennessee landscape.