What Is The Best “Old School” Trail Race

March 9, 2014 in Article by Eric Eagan

The Trail Runner Blog Symposium is ripe for debate this month  – I figured I would chime in for my ultimate “Old School” trail race. I know for one, that each of the #TrailsRoc board members who have access to this page will likely have a different answer – That is part of what is so great about our sport, the fact that there are so many amazing races – and even many that qualify as Old School.

This race is literally the oldest trail race in North America and still requires mail in registration.

Think about that for a second – We live squarely in the height of the internet era and the online world and yet registration is done first come, first served via paper mail in registration. None of this lottery, none of this “hope your internet connection is fast and working” the minute registration opens.

Just an old school trail race with a crazy system for entry that favors locals, cares about the environment and has a crazy handicapping system that enables an 8 year old to girl to hold off every runner in the field to run to victory in 2011. 

I am writing about the top race on my bucket list – The Dipsea Race. First run in 1905 – the Dipsea race automatically qualifies as old school. It is in fact the oldest of Old School. There is an aura about this race – It’s impossibly hard to enter for a guy from Western NY. It’s care for the environment, but most of all the trail and the terrain.

Trail stairways as high as 50 story buildings. Running into the John Muir Woods, can anyone say Redwoods? A trail named cardiac and best of all “Insult Hill” – A steep incline that does what it sounds like, insults  you. You pretty much end in the Pacific Ocean – which I have only seen one time in my life for 10 minutes.

Dipsea is as classic and old school as it gets – I encourage you to take a look – Add it to your list but more importantly, join the conversation. Leave us a comment – what do you think is the best old school trail race – 




Eric Eagan Eric Eagan (53 Posts)

Eric Eagan is is an avid and passionate runner living in Greece, NY. Eric tells his stories about the Western NY running scene in a unique way while sprinkling in his goals of motivating others to start running, keep running, and love running.When Eric is not running or writing about running, he is hiking the Adirondak Mountains, the Finger Lakes Trail, snowshoeing the trails and hills of Western NY, or canoeing the waterways of New York State.