How to carve out a niche of challenging mountain races

By Henry Howard

Steven Estremera has created a niche of trail and ultra running in upstate New York, focusing on challenging mountain races. While his courses are challenging and offer significant vert they aren’t necessarily super long.

Case in point: his Plattekill Mountain Race is only 6.5 miles but offers 3,500 feet of gain. Beyond creating challenging courses for the athletes, Estremera also makes it a priority to “give the runners the best experience you can.”

For his contributions to the trail and ultra running community he is my featured race director for June. In January 2024, I kicked off this monthly feature to pay tribute to the trail and ultra race directors who make the sport great. To see previous RDs featured, they are all available here. If you have any nominations, feel free to email me here or fill out this form.

Meet Steven Estremera, Conquer the World race director

Question: Why did you get into race directing?

Answer: When we started there was a hole for trail racing in the area (Dutchess County, N.Y.). We wanted to give people a platform to experience their first trail or ultra race and build a strong trail running community. Seeing runners come out for their first trail race, their PR, the struggle and sense of accomplishment on their faces when they finish is what drives me to keep doing this.

Question: How did you get your start as an RD?

Answer: I race directed a 5K while in college, and a classmate and professor of mine had an idea to start a company to host trail and ultra races and CTW Endurance was born. It's not our main career but something we enjoy and will keep doing.

Question: What's the most interesting thing you've learned about yourself since you became an RD?

Answer: That I truly love making courses challenging. I look for the most efficient way to incorporate as much vert as possible in the trails I have to work with.

Question: What's your best piece of advice for someone who wants to become an RD?

Answer: It's a lot of work, but it's rewarding on race day. Don't go half ass on any aspect of a race. Give the runners the best experience you can.

Question: What's your favorite race to direct?

Answer: The Plattekill Mountain Race. (6.5 miles and 3,500 feet of gain). It's a brutal course and our first "mountain race" so I love seeing the runners come out for the challenge.

Question: What's your favorite race to run?

Answer: The Breakneck Half Marathon in Cold Spring, N.Y., is probably my favorite race to run.

Question: Tell me about a funny experience as an RD and what you learned from it.

Answer: No matter how many times you think you marked the course correctly or effort you put into course marking someone always misses a turn. It's just funny and frustrating at the same time. Ha ha.

Question: If a runner can only do one of your races ever, it would be ...

Answer The Pawling 24 hour Trail Running Festival. It's a cool experience on a half paved/half trail loop where runners see how far they can go in 24, 12, 6 or 3 hours. We have only had a few people break 100 miles so it is a great challenge and experience

Question: What exciting project do you have in the works?

Answer: We are in early talks for some big adventures up north.

Question: Where can runners find out more about your races?

Answer: https://ultrasignup.com/groups.aspx?gid=421