Hawaii is home to some of the worlds most exciting outdoor activities due to it’s year round perfect weather. Skateboarding is easily one of the best ways to pass the time in Hawaii with the amount of concrete that is on Oahu along with the surfing atmosphere. In reality there are many streets and roads that are great for downhill skateboarding in Hawaii and listing the best on one list is virtually impossible. Best way to experience these roads is to grab your board and cruise around the town because you’re bound to stumble upon a road, street, or alley that meets all of your needs. Oahu is home to awesome roads and streets for downhill skateboarding enthusiasts and the surfer who enjoys a good cruise on a longboard when the swell is absent.

5. Round Top Drive (Tantalus)

Located on the backside of Tantalus, Round Top Drive offers a challenge to even the most experienced of downhill skateboarders. This winding, curving road is the epitome of a “hairpin turn,” which gives a regular footed (left foot forward) skateboarder the opportunity for an extremely fast right carve directly in front of a lookout where that kind friend of yours can sit with your camera and get a perfect shot. For goofy footed (right foot forward) skateboarders, this spot presents the challenge because rarely you’ll find someone who likes making a turn going in the direction that their back is turned. The chance of catching an edge of a wheel and going flying forward is always a possibility when making such a turn. If he or she knows how to do a front side slide to fakie (when your dominant foot is leading) it probably your best bet at making this turn.

This spot gets a four on a scale of one to five for danger due to the curvy nature of the roads and the amount of traffic that goes through the spot. Tantalus has amazing views of the sunset over Honolulu, which makes it an ideal location for a group to go skate as long as they are cautious of the traffic in the area.

4. Diamond Head Road (Honolulu)

The lookouts at Diamond Head offer some of the best views of surfers from the comfort of an extinct volcano. Skating down the side of an extinct volcano is an amazing experience especially on Diamond Head Road where one will find smooth black pavement that presents itself parallel to the ocean and a series of parks and crashing waves. This road gets a two on a scale of one to five for danger because there is a bike lane and the road flattens out at the bottom, which gives riders plenty of time to slide their front foot along the ground to slow down before the intersection. Overall the only fear at this spot is gaining too much speed, resulting in the speed wobbles.

3. Wilhelmina Rise (Kaimuki)

This spot is very dangerous. On a scale of one to five for danger it gets a solid five. Wilhelmina Rise is extremely steep and is a straight downward slope that has parked cars along one side of the old cracked road. Board slides to slow down are mandatory on this hill, and if one is not used to board slides I would recommend trying a less steep hill. If anything start from a third of the way up and drop into it from there, speed builds up faster than you expect on this road and cracks pop out of nowhere.

2.Kapahulu Avenue (Honolulu)

One of the longest rides that one can get on the South Shore of Oahu is Kapahulu from the H1 overpass all the way to the Waikiki Fire Station. This 1.5-mile ride is riddled with stoplights and tourists driving rental cars who are not the safe drivers. If one is looking for an interactive skateboard ride, Kapahulu is the road for you because where the sidewalks meet the roads there are little slopes that allow one to gain more speed. On a scale of one to five for danger it gets a five due to the amount of traffic flow that is on this road. Be careful and don’t fly through red lights, you will get hit.

1. 10^th Ave (Palolo Valley)

The longest, fastest, safest road for downhill skateboarding on the South Shore of Oahu is 10^th Avenue from the back of Palolo Valley all the way to the intersection at Waialae Avenue. It is safer for runners to run against traffic in order to see the cars coming toward them so they do not have to worry about getting hit from behind. If one employs this philosophy on 10^th Avenue one can cruise at high speeds in the bike lane going against traffic for roughly five minutes. The best time to skate this road is in the early morning before the huge rush of traffic to work. The road will be empty the entire way to Waialae, and it will really emulate the experience of an extremely long wave.