Living in the age of AI has its benefits: a rookie like me can access advice to pursue what might otherwise be out of reach. How do you define a dream? It scares me, it thrills me, and I’ve already started self-sabotaging by not biking at all since Labor Day weekend. So, it’s probably a dream. And how does an accountant get started on a dream? With a spreadsheet, of course. How else does one schedule or organize anything…
I clearly know what I’m doing, so I’ll start by asking Google: how do I create a bicycle road race schedule for a season? Google AI Overview (which machine is this anyway? Gemini? ChatGPT?) gave me this sage advice:
- Set your goals
- Map out your annual calendar
- Plan your training phases
- Strategize your race blocks
- Find events and track your progress.
Does that seem obvious? Yes. Absolutely. Now I feel boldly capable of developing a schedule that is likely biting off way more than I can chew… Ok I’ll read these articles Google scrounged up for me. Planning the Year of Cycling Racing and Training and 7 Tips for Planning Your Race Calendar. Thank you, internet! My initial impression of the first article is to be pumped that its featured photo is of female cyclists racing. I’m encouraged that I’m part of their targeted demographic.
Key takeaways: come up with a dream list of races, identify your priority (“A”) races, training (“B” and “C”) races, slash and schedule the list, plan rest in your training schedule, and seriously consider finding a coach or trainer to work with. From here the next step is fun… I get to go window shopping for bike races! What are the most interesting races out there? Time to check out usacycling.org.
Here’s what seemed interesting, and some ideas are waaaaay out of my comfort zone.
- Gran Fondo Florida – March 22, 2026 – 98 miles, 3063’
- 2026 Garden State Road Race – April 18-19, 2026 – TT (6 mi), Road Race (30 mi), and Circuit (17 mi)
- Crazy 8 2026 – May 24, 2026 – 108 miles, 14500’ gravel ride
- Killington Stage Race – late May – is this happening in 2026??
- Vermont Gran Fondo – late June 2026 – 109 miles, 9800’
- Training ride idea – 200 miles: all of route 100 in Vermont
- 2 Days of Buffalo – August 1 & 2, 2026 – stage race with TT & crit on day 1, road race on day 2
- Tour de Wyoming – July 12-17 (gathering on July 11) – not a race, but training opportunity
Now I have so many more questions and I’m a little overwhelmed. Also, I’ve had friends mention earning points at various races throughout the season to improve their category for racing. This is beneficial especially in criterium races, which, quite frankly, scare the daylights out of me. I’m going to have to turn to my community for more information! I’ll keep you posted as I learn more.




