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Some people plan romantic getaways for their wedding anniversary. For my 19th, I registered for a cycling hill climb on Saturday, August 15, 2026. The guys at Bike Doctor Annapolis made me do it, I swear. :)

If you know me, you know I love cars and driving just as much as bikes and climbing — which makes this especially intriguing. The race goes up Mount Washington’s famous Auto Road: a 7.6-mile, grind to the highest peak in the Northeast. Many consider it the steepest cycling race in the world, and VeloNews dubbed it a “Ride of a Lifetime.”

Fun fact: Mount Washington is home to some of the worst weather ever recorded on Earth, including a 231 mph wind speed at the summit. Hurricane-force winds show up about 100 days a year. Fingers crossed no weather issues this year.

Even better, the climb is a fundraiser for Tin Mountain Conservation Center (TMCC), which has provided environmental education to more than 75,000 students across Northern New Hampshire and western Maine over the past 34 years. You can see some of their great work on the TMCC YouTube channel.

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