Calling Drew Sheppard’s goals “ambitious” is like calling his hometown New York City Marathon a local fun run. While many people treat the distance as a one-and-done bucket-list endeavor, Drew’s first marathon opened the door to bigger and bolder challenges, most notably his triumphant 16-year mission to complete a remarkable triad: running a marathon in all 50 U.S. states and on all seven continents, along with the six World Marathon Majors (Berlin, Boston, Chicago, London, New York City and Tokyo).
A marketing executive and long-time RaceRaves member, Drew showed unwavering resolve throughout his quest despite setbacks that included a global pandemic. And while countless hours spent training alongside his New York Road Runners and Galloway NYC Running Club teammates prepared him both physically and mentally, the real secret to Drew’s success may lie in the upbeat attitude and positive mindset he brings to each and every start line.
RR: Are you a life-long runner? What inspired your ambitious (some may say crazy!) goal to run all six World Marathon Majors, plus a marathon in each of the 50 States and on all 7 continents?
DS: I am not a life-long runner! In high school I went out for Winter Track my sophomore year. For tryouts the coach made us run two laps of the track and I struggled. I don’t think that anyone expected me to come back the next day, but I did and I stuck with it for the next three years. While I liked being on a team, I never actually enjoyed running back then. Once I graduated in 1989, I stopped running completely.
When I moved to NYC after college, I created a bucket list of things I wanted to do as a New Yorker—for example, go to the Village Halloween Parade, take a horse carriage ride in Central Park, and see a taping of Saturday Night Live (which is still on the list 30 years later—I haven’t been able to get tickets yet!). In the mid 2000s I added “Run the NYC Marathon” to the list. The marathon goal was meant to be a one-and-done thing. I got in for November 2007 and did zero training, so I deferred to 2008.
I then set about looking for help to get me to the starting line. I started with New York Road Runners Group Training classes twice a week. There I started to learn the basics about running—the right shoes & clothes, the correct running form, and how to breathe properly. That was hugely valuable. I also met the most amazing person—M’Shell Patterson—who introduced me to the Galloway NYC Running Club, and that completely changed my life.
I attended their marathon training kickoff session where a member (Elvia Negron-Perez) stood up and talked about how she was on a quest to run a marathon in every state, and I thought that was the coolest goal! I hadn’t run one marathon yet, but I was already thinking “Hey, I want to do that, too!” So initially my goal was “just” the states.
As a new marathon runner, I was consuming all the information I could get. Eventually I heard about the Antarctica Marathon and knew that I had to do that, too. So then the goal expanded to all the states plus all the continents.
From there, I realized that if I ran Tokyo as my Asian marathon and London plus one “extra” (Berlin) for my European marathon, I could knock out the six Abbott World Marathon Majors as well (as long as I did NYC, Chicago, and Boston for their respective states).
RR: Any of your three achievements by itself would be a bucket-list goal, but if you could do it all over again and conquer just one of the three, which would you choose and why?
DS: It was pretty amazing to do all 7 continents, but if I had to pick just one of the three, it would be the 50 states.
This is such a beautiful country! I knew that the Maui Oceanfront Marathon (Hawaii) and the Big Sur International Marathon (California) would be great trips, but I was surprised by how spectacular the Anchorage Mayor’s Marathon (Alaska) trip was.
Also, I loved seeing Mount Rushmore (Run Crazy Horse), the Gateway Arch (Greater St. Louis Marathon), and Graceland (St. Jude Memphis Marathon) to name just a few of the many attractions on my marathon journey.
Additionally, I met so many wonderful people. Despite all the talk about the polarization of the country, that has not been my experience. Traveling around meeting other runners with all different backgrounds, I found that people are basically good, with all of us just trying to do our best.
RR: By design, you completed your 50th state and 6th Major in one fell swoop at last month’s Boston Marathon, after completing your 7th continent (Asia) in Tokyo in 2023. Of all the races you’ve run, I think we can agree Boston is a uniquely overwhelming experience. So what were you feeling after crossing the actual finish line in Boston as well as the figurative finish line to an amazing personal journey?
DS: The day was everything I wanted it to be. It was the first of my 62 marathons where I started the race completely free of anxiety. Normally I have nervous jitters at the start. Not this time. I was just so happy to be there, and I felt so supported.
I had family there (Mom, Dad, and Aunt) as well as several friends from NYC—including a couple of running coaches—and local Boston friends from college. M’Shell Patterson (mentioned above) was volunteering that day, as she does every year. She escorted me onto the runner bus in Boston Common in the morning and was the first person I saw when I crossed the finish line on Boylston Street—bookending my day in addition to bookending my entire marathon journey.
I definitely shed tears of joy. Plus, I received two medals—the Boston Marathon medal and the Abbott World Marathon Majors Six Star Medal. It was a perfect day! To be clear, the weather was too warm and it was a tough course, but neither of those facts took away from the specialness of the day for me.
RR: With so many marathons run across the U.S. and around the world, are there one or two (aside from Boston) that really stand out in your mind? How about a hidden gem or two everyone should know about?
DS: For me, it was always about more than just the race—it was about the whole weekend experience. I definitely ran and enjoyed a lot of the popular marathons (including Grandma’s, Flying Pig and Fargo), but two of my favorite trips were the Prairie Fire Marathon in Wichita, Kansas and the Queenstown Marathon in Queenstown, New Zealand.
I did the Prairie Fire Marathon with my friend Lynn Pelowski, and it was the most fun finish-line experience I’ve ever had. When I went to New Zealand I really pushed myself out of my comfort zone, including ziplining for the first time (I hate heights).
RR: Besides a wildly impressive collection of medals, what was the most rewarding aspect of your 50 States/7 Continents/6 Majors journey?
DS: I love that I found my inner athlete when I was 37 years old. For most runners, being asked “How’d the race go?” really means “How’d you feel about your performance?” rather than “Did you win?” The sport welcomes people of all ages and abilities. It’s also a great way to explore a new place as you can literally do it anywhere.
RR: Speaking of medals, we’re always open to new ideas so we have to ask—do you store yours in the closet, display them on a wall, or something else?
DS: I am VERY proud of my medal display! I have a narrow entryway to my apartment which is perfect for my wall display. I have shelves with shadow boxes for each marathon. Each shadow box includes the marathon medal, date of the marathon, and my finish time. My half marathon medals hang on bars below the marathon shelves.
RR: A goal like 50/7/6 requires an inordinate amount of planning, patience and flexibility, both mental and physical. No doubt the pandemic threw a monkey wrench in your plans, but were there any other notable setbacks (i.e. injury, loss of motivation) along the way?
DS: The original goal was to complete this quest the year I turned 50 (2021). COVID obviously changed the timetable, but I never lost the motivation.
I had a couple of injuries along the way, the biggest requiring wrist surgery in 2012. I had to cancel the spring marathons I had registered for, but I added replacement races later that year so I still completed four marathons as originally planned.
As I neared the completion of my goal, I also experienced my first-ever DNF (Did Not Finish) at the Big Five Marathon in South Africa when I got pulled at mile 17. It was the right call, as I wasn’t doing well, but it was a humbling moment that made me a little apprehensive for my next marathon. I knew that I had to sign up for a replacement immediately so that I could quash any doubts I had.
Four months later I went back to South Africa to run the Cape Town Marathon. It was a good life lesson in perseverance and determination. I would have preferred to learn the lesson closer to home (say, Connecticut, just a train ride away) versus halfway across the globe, but what can you do?
“I love that I found my inner athlete when I was 37 years old.”
RR: Anyone who’s tackled an audacious goal like yours knows that no man (or woman) is an island, and success requires support far beyond the best aid stations. Who has been your support crew throughout your journey?
DS: I feel so blessed to have so many people in my corner. First and foremost are my parents. They came to watch me run the Walt Disney World Marathon in 2009, and then they went from spectators to participants. My Mom has since run two half marathons, nearly a dozen 10Ks, and over 100 5Ks. My Dad has accompanied me on many of my running adventures and has participated in a handful of 5Ks himself.
Both my NYRR Group Training and Galloway NYC Running Club groups have been incredibly supportive and were key to helping me retain the joy on this journey. I’m also grateful to Marathon Tours & Travel, with whom I traveled for most of my international marathons. Turning over some of the travel logistics on this quest was hugely beneficial.
RR: You’ve proudly called Boston your 62nd and final marathon. Now that you’ve had some time to reflect on, process and savor your achievement, what’s next in your running career?
DS: I love running and will continue to do so. The half marathon is my favorite distance. Eventually I’ll complete a half marathon in all the states as I want my RaceRaves map to be completely green (I’m currently at 27 states plus DC)!
I will also continue to combine running and travel—there are so many places that I want to visit! Someone just told me about the SuperHalfs Series (Lisbon, Prague, Berlin, Copenhagen, Cardiff and Valencia), and I’ve completed one of the six (Prague) so I’m intrigued….
RR: What advice—race day, travel, or otherwise—would you give someone who thinks they may want to follow in your (many) footsteps, but who isn’t sure how to approach such an expansive and long-term goal as running in all 50 states or on all 7 continents?
DS: I love a detailed spreadsheet, and that’s how I began! I suggest starting with a clearly defined North Star—the ambitious and overarching multi-year goal. Then:
- Break down the goal to the more immediate term and get specific about the next year or two.
- Be open to changes, and prepare for the occasional setback. Life will happen. Flexibility is important. Races get canceled, family events get scheduled that require adjusting previously set plans, injuries occur, etc.
- Do the research (RaceRaves is a great resource 😀).
- Identify your support crew—family, running clubs, coaches, physical therapists—who will help you achieve your goal.
- Do the work, and frequently evaluate how things are going to identify what is working and what needs to change.
👉 Follow (and contact) Drew on RaceRaves to stay updated on all his racing adventures, including his quest to run a half marathon in all 50 states!
Looking for more running events? Search for races by state/city or month, and try our handy Find a Race tool to search for events by name, date range, distance, location, terrain & more. Then sign up for a free account to build your wish list and start coloring in your 50 States Map!
Author: Mike Sohaskey
Mike Sohaskey is the co-founder of RaceRaves, the premier online reviews community for runners to share their race experiences and find their next challenge. Mike honed his creative and critical thinking skills as a research scientist, earning a Ph.D. in Cancer Biology from Stanford. He’s also completed over 100 races — including 50+ marathons and ultras — in locations ranging from Antarctica to Zimbabwe.
Other RaceRaves articles you’ll enjoy (trust us!)
Lunatic Spotlight: More Alike than Different
Lunatic Spotlight: One Year, 100+ Races
Lunatic Spotlight: 50 States the Hard(er) Way
Lunatic Spotlight: Unbreakable
Lunatic Spotlight: Racking up the (s)miles
Lunatic Spotlight: A Race Of Her Own
And for more helpful articles, check out our blog!
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