Big South Fork Railway - Sit back and enjoy the breathtaking scenery of the Big South Fork National River and Recreation Area while the train makes its way through deep gorges and hugs steep cliff lines to take you back into a bygone era of logging and coal mining.

Cumberland Gap General Store - Cumberland Gap General Store is the largest and oldest retail gift outlet in the Historic Towne of Cumberland Gap, TN. The store carries over 6000 items in stock, including household decorative items. The business opened in 1946.

Cumberland Gap National Historical Park - Follow the footsteps of early travelers along the Wilderness Road, experience the stories of the pioneer, the Civil War soldier, the traveler. Historic buildings and sites throughout the park provide opportunities to take a close look at the events that shaped a region and a nation. Tours of the historic Hensley Settlement showcase life in the Southern Appalachian Mountains.

Cumberland Gap Tunnel - The Cumberland Gap Tunnel is a 4-lane twin-bore mountain tunnel that is 4,600 feet long and carries US-25E under Cumberland Gap between Tennessee and Kentucky. It was completed in October 1996 at a cost of $280 million.

Gap Cave - The cave closely resembles its original condition. No electricity - only lanterns light the way. Visitors will discover mammoth rooms and gaze in awe at the walls decorated with delicate stalactites and majestic stalagmites.

Festivals in or near Cumberland Gap:

Rockwood Family Fall Festival - Rock climbing, bungee run, speed pitch cage & radar, velcro wall, cow milking contest, fire truck slide, mechanical bull, 50ft obstacle course and more. For the little ones, petting zoo, pony rides, Mr. Brain and the Boppits. Pretty baby contest all the way up to Miss Rockwood Beauty Pagent. Carriage rides from 11am - 5pm. Festivities start at 10am.