Cowboys Orlando

Originally founded as a small bar named Trailway’s, this family-operated venue has grown into a 20,000-square-foot destination for country music enthusiasts. It is anchored by a massive hardwood dance floor—celebrated as the largest in Orlando—where guests gather for two-stepping and line dancing. The facility includes seven fully stocked liquor bars, billiard tables, and a large outdoor patio area. On Thursday and Friday nights, the staff provides free line dancing lessons to help newcomers learn the ropes. The venue maintains a specific dress code and frequently hosts themed nights focused on classic country hits. Located on South Orange Blossom Trail, the bar sits within fifteen minutes of the city’s major theme parks and the downtown district. On weekend nights, an on-site food truck serves western-style dishes to the late-night crowd.