Measure the length of the oak barrel and mark its center. Extend this mark around its center, forming a straight line.
Cut the oak barrel into two halves, using a handsaw and applying steady pressure while cutting over the chalk line. The base of the barrel serves as the base of one planter, while the top of the barrel forms the base of the second planter. Smooth out sharp edges or splinters on the tops of the two planters, using sandpaper.
Bore four to six 1/2- to 1-inch evenly spaced drainage holes through the base of each oak barrel planter. Set each barrel planter over the spot where you want to display the container garden. Make sure it receives the amount of sunlight required for the plants it will contain. Set three to four bricks on the ground and center the base of the barrel planter on them. Raising the base of the barrel planter higher than the ground prevents drainage problems.
Pack the barrel with quality potting soil amended with organic matter such as compost or manure until it's two inches below its rim. Alternatively, create your own growing medium by mixing equal amounts of peat moss, sand, compost and potting soil, and pouring it into each barrel planter. Smooth the top of the soil medium with your hand.
Plant seeds or seedlings of the desired plant varieties in the planters, following label directions for spacing and depth. Insert stakes, trellises or commercial cages to support growing plants. Secure growing tendrils of vining plants to the support structures with elastic ties or soft cord.