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Hi Lauren, I am doing the DitR race this year but have done the Williamsburg Olympic probably the last 5 years and its a great fun course. The bike is about as fast abnd flat as it gets. Long stretches coming back in the tall pines that is straigth as the arrow goes. The only hills really is the bridge over and back the Chickahomony river which you swim in. The swim is usually fast and short due the tides going out in the morning and river current. I hit my best swim times here even slogging through the muck near the shore. Definitely a good race. Can be a little humid there in July so train in the heat which here in DC isn’t very hard to find. OH and treat yourself to dinner in Colonial Willamsburg after the race at one of the historic taverns. Lots of fun.