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Muskoka 70.3 Bike Course, in musical terms.
T1 to Britannia - Any track by The Doors, but probably Roadhouse Blues. Try to get in a rhythm. There are precious few stretches on this course that will allow you to get in a rhythm.
Britannia - Early Godspeed! You Black Emperor. It feels long and changes volume a lot. Try to time the song in your head to peak at the top of the big climb.
South Portage Road - Some shitty Spotify commercials because you are too cheap to pay for a subscription. Boring and uneventful.
Dwight Beach Road first 2 km - Imagine you are driving a late 80s Pontiac Tempest when your favourite road trip mixed tape is chewed up by your car stereo, ejected, and your radio spontaneously tunes to frequency just adjacent to a Christian preacher radio show with loads of static, cranked to maximum volume through those old 8" oval 3-way speakers with the paper cones. Alternate: the sound of crappy carbon rims exploding in potholes, interspersed by the screams of triathletes absorbing gravel into their bloodstream. This stretch is not in good shape.
Rest of Dwight Beach Road - Margaritaville
Hwy 35 to Dorset - The sexiest R&B you can find. It's foreplay for the rest of the ride, and thinking about the effect of Marvin Gaye or old Diana Ross on your significant other will help you to forget about the heat and large trucks blowing past on rolling, shoulderless roads.
The climb out of Dorset - Probably "Life is a Highway" by Tom Cochrane. Not that shitty version by some country band. This song actually has little to do with this leg searing hill, but there is a 99.2% chance that someone will be blaring it from their boat or car as you ride through town, so why fight it.
Highway 117 to Baysville - Your favourite road trip album. Slap it in the big ring and enjoy. You will pay the price later, but who cares?
Brunel Rd to T2 - I would lean towards some Pantera or other popular metal or thrash, just to keep the adrenaline going on this rolling, curvy stretch, but since you probably overcooked at least 40% of the bike, some songs about regret might be appropriate as you dump into the granny gear to get over very small lumps in the road. Towards the end of the road, definitely "My Way" - either Frank's version, Sid's version, or that awful Bono/Frank remix - depending on how you paced the race to this point.