A Tale of Two Tecumsehs (A Would You Rather style game to choose your own adventure)

I felt a little guilty with how Tecumseh and I left things on my hike last week, and from your feedback I learned that:

1. My big bum would prefer butt sledding this trail in the winter
2. The trail on the Tripoli side is the preferred route
3. I should probably start seeing a therapist to work out my anger issues

Well, since mountain therapy is far cheaper than actual therapy, I opted to give Tecumseh a second chance – this time over on the Tripoli side – and it was WILD, as in wildly good! No stairway to death, just a lovely walk in the woods – but yes, same bleh summit.

That being said, I know that some of you psychos out there really love Tecumseh from the Waterville Valley side, so I thought we would play a little game of Would You Rather to help you figure out which Tecumseh is right for you:

(photos in this post are from the Tripoli side trail, and featuring my trail pup Teddy – no stink face selfies of my ugly mug on this hike!)

Would You Rather….
A. Drive down a well-paved road while being assaulted by Waterville Valley tourism signs? Then after you have parked – in the admittedly ample-sized parking lot – wander around in circles trying to figure out where the actual trail starts?
(note for the directionally challenged: the trail is across the street from the parking lot)
B. Or travel the amusement park ride that is Tripoli Road, bumpin’ and swervin’ around aggressive potholes, campers from Mass, and narrowly escaping a hawk taking a dump on your (open) sunroof?

Would You Rather…
A. Stomp up and down stairs continuously for 5-miles because monotony is fun – and besides, who needs knees anyway!?
B. Or experience a variety of terrain from moderate forest-walking to some rocky patches with a few fun little scrambles along the way?

Would You Rather…
A. Hike less miles with more elevation gain per mile cause you need extra gainz for dat keto life brah!?
B. Or add a mile to your hike in exchange for more moderate grades, because you’re a reasonable person and know that balance is key in both in hiking and in life?

One of many butterflies I saw on this hike!

Would You Rather…
A. Be chased up and down the trail by mosquitoes and black flies, and get your fastest hiking time yet with a side of West Nile virus?
B. Or peacefully coexist with – surprisingly friendly – spiders (whose webs you will inevitably knock down), and a shit ton of butterflies who will flutter around you happily like you’re a mutha fuckin’ Disney princess?

Would You Rather…
A. Be constantly passing people going up and down the trail, who – like you – are all going through some stage of existential hiking crisis, and having to do the awkward “No, after you” hiking dance, when all you really want to do is bum rush past them and get this hike over with?
B. Or experience the quiet solitude of hiking alone, because (for you) Covid times were the best of times and you’ve completely forgotten what (little) social skills you had to begin with?

If you answered mostly A’s: They say that the definition of insanity is repeating the same thing over and over again and expecting a different result. You value ample parking space over healthy joints, and find monotonous trails oddly soothing. Congratulations, you’re insane! And, Tecumseh via Waterville Valley is the trail for you!

If you answered mostly B’s: Who needs shocks on your car when you can experience butterfly kisses and a remote trail that you’ll likely have all to yourself. You’re wild, and you most likely don’t really like people all that much. Tecumseh via the Tripoli Road side is the trail for you, lone wanderer!

How did you do? Comment below with your result!


  1. Jackie
    June 25, 2021

    I definitely would have gone all Disney Princess!
    This was hilarious and very clever. Loved this blog!!

    1. Jennifer Crossett
      June 25, 2021

      YAS! Important question: which Disney princess is your spirit animal? I’m an Ariel! ?‍♀️

  2. Rich C
    September 16, 2023

    Fully agree. I only do the Waterville side when required (winter). B all day!


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