The Blackjack Trail is one of the two intermediate-level trails at Bales Park alongside the Bootlegger. The rock features, especially on the lower west section, make it challenging. However, it can be fun to ride given that the upper east section is mostly a descent if you through the trail clockwise instead of the other way around.
Also, some people combine it with the other trails at Bales Park since it is pretty short, at 1.61 miles, and will take only a few minutes to complete.
Blackjack is a mid-park trail at the park, so you’ll have to ride to the trailhead using Lookout Ridge Trail. However, you’ll need to get to Bales Park before you can get onto the trail system. If you’re coming from Tulsa, you’ll get on U.S. Route 66 southbound, then past Cherry Creek, take a left onto S Union Avenue. Stay on S Union Avenue for about 1.9 miles, and you should come across the Bales Baseball Park with the parking lot on your left.
Once you take out your bike, a trailhead on the east end of the parking lot puts you on the Lookout Ridge Trail. From there, you’ll head northeast on the trail as it meanders, then turn north near the Okmulgee Expressway. Keep following the trail until you reach a trail hub where Lookout Ridge, Little Rock, Bootlegger, and the Blackjack Loop converge.
The trail furthest to your left is the Blackjack. Most people ride it as part of the Bales Baseball Park outer loop. As such, they ride through Blackjack downhill to the intersection with Little Rock and Bootlegger. From there, they take Little Rock up the hill, which should take them back to the first hub.
This cuts out the Bootlegger Trail from the equation since it cuts between Little Rock and Blackjack.
We noticed that the west section near the Little Rock and Bootlegger intersection is significantly more difficult than what you get near the Lookout Ridge intersection.
Sure, you’re going downhill, but the trail is skinny in some sections with many rocks you can’t avoid. Nevertheless, riding the Blackjack shouldn’t be too difficult for an intermediate-level rider since the entire trail system is relatively small.
Also, for those who skip Bootlegger while going through the outer loop, the other two trails, i.e., Little Rock and Lookout Ridge, are ranked easy.
There aren’t any noteworthy sites at the Bales Baseball Park, although you only need to cross the Okmulgee Expressway to the Turkey Mountain Park, and from there, the Arkansas River is just a short distance away.
10 mi 
