A railroad from Bristol to Big Stone Gap was first conceived in the mid-1850s, but construction was postponed by the Civil War until the 1870s, construction aided by convict labor from Richmond. First belonging to the Bristol Coal and Iron Narrow Gauge Railroad Co, passenger and freight service began in May 1890 and flourished on this line, now called the South Atlantic and Ohio Railway (1890) or the Virginia and Southwestern Railway (1899), until service as Southern Railway (U.S.) ceased in 1972.

The last passenger train ran in 1947. In 1951, the last steam engine was retired and replaced by diesel powered engines. In 1970, the last Southern trains ran on this branch. During it's heyday years, the most famous steam train on this route, going all the way to Cincinnati, was the Lonesome Pine Special.

After flooding destroyed trestles in the 1970, the ROW was leased by Southwest Virginia Scenic Railway and passenger excursion trains ran in 1972-75 and 1981. Eventually, around 1987, the decision was made to create the Lonesome Pine Special Trail by The Lonesome Pine Recreation Corporation and tracks were removed, but progress was held up for many years by lawsuits.

Around 2000, The City of Bristol, Virginia purchased much of the land consisting of 14 miles of former railroad right of way with plans to create what would now be know as the Mendota Trail. Quite a few citizens donated money to get that trail off the ground, which the city spent buying the property. The Project was held up for many years by lawsuits and finally Bristol gave up on their Trail effort in 2008.

In 2016, The City of Bristol, Virginia. gave away this land Right of Way to the Mountain Heritage Inc. nonprofit, and a new effort began to make the trail a reality. Although still contested by some adjacent property owners, in a 2007 court document dealing with a review of individual claims against the Mendota Trail project and the possibility of the land reverting to original owners, Circuit Judge C. Randall Lowe wrote “the court finds the deed states if the railroad is built then the possibility of reversion is extinguished. The railroad was built. Therefore, the condition of reversion was satisfied and the railroad and its assigns owned a fee simple interest in the property conveyed.” Thus, the railroad property Mountain Heritage owns in fee simple is no longer public property.
In late 2020 ownership was transfered to the Mendota Trail Conservancy Inc.
While the trail control by the MTC will remain intact, the ownership of the Trail will transfer to Washington County, Virginia in mid 2023, providing much needed resources for the longivity of the trail.

Currently only the first four miles from Mendota south to the Holston River Trestle and up the gorge to Leonards, and the first six miles beginning at Bristol's I-81 to Benhams and through the Cut are open to the public, but other sections are currently being prepped for use.

When complete in the summer of 2023, the trail will extend from Bristol, past the old railroad stops at Walkers Mountain (later called Haskell Station), Benhams, Phillips, Abrams Falls and across the North Fork of the Holston River and end at Mendota.

1900 February first train steamed between Abindgon and Damascus on the Virginia-Carolina Railroad
1912 the V-C railroad was extended to Whitetop Virginia
1918 the line stretched 75 miles to Elkland, NC (now named Todd, NC), and included more than 100 trestles
1957 The last steam engine retired, replaced by Diesels
1977 March 31 After flood damage, Abingdon Branch of the Norfolk & Western Railway abandoned & track removed same year
1977 Summer Washington County Planning Commission discuss Trail possibility
1978 the U.S. Forest Service purchased the 14 mile right-of-way between Damascus and Green Cove for a hiking/biking trail, and soon afterwards, the remaining 4 miles to Whitetop
1982 Abingdon and Damascus purchase entire right of way from N&W, for $13,000. (another $155,000 of State & Federal funds were used for the Trail Project)
1984 Decking work, mostly by Job Corps, completed except for burnt trestle #6
1987 June Virginia Creeper Trail was dedicated as a National Recreation Trail
1989 mid-summer Virginia Creeper Trail was open from Abingdon to Whitetop

1866 East Tennessee & Western North Carolina Railroad granted charter
1882 ET&WNC begins operation of 32-mile narrow-gauge service from Johnson City TN to Cranberry NC
1919 ET&WNC extends tracks to 66 miles for service to Boone, N.C.
1940 August Torrential rains wash away large sections of ET&WNC track ending service to Boone
1950 July 13 ET&WNC abandons route between Elizabethton and Cranberry NC. All Track pulled up and ROW deeded to Carter County
---- Discontinues all narrow-gauge rail service. All of its steam locomotives are scrapped or destroyed, except for locomotive No. 12
1960's Late. Doe River Gorge Playland, a small amusement park laid tracks along three miles of the gorge, became Hillbilly World in 1971
2003 October 10 East Tennessee Railway abandons route between Johnson City and Elizabethton
2005 Organization begins to create a Trail
2011 April Johnson City initiates negotiations with the ET Railroad, and the corridor was successfully railbanked
2012 Rails and ties were removed to make way for the trail. Sponsors found to cover most expenses reduced cost drastically. NO grants were sought in the early phases to reduce the timeline and attached strings/ limits
2013 December Acquisition was complete and the work to build the trail begins
2014 August Tweetsie Trail opens first 5 miles to Elizabethton
2014 September Tweetsie Trail expanded to 7 miles into Elizabethton
2015 August Tweetsie Trail expanded to full 10 miles across Elizabethton
2022 Land donated to expand Tweetsie Trail from Valley Forge to Hampton
2023 April 6.3 million bugeted by TN to expand Tweetsie Trail from Valley Forge to Hampton including trestle at Tunnel #1 and Hampton Watershed Trails Expansion