After an unfortunate incident very similar to the OP, Malkin and I ALWAYS walk unfamiliar obstacles like railroad tracks and broken-up asphalt. We also walk obstacles that we know all too well. This gives us practice on starting and stopping, and avoids pinch flats and bent wheels.
Cheers!
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2008 Red Co-Motion Speedster Co-pilot (Redster)
2009 Surly LHT (captain's commuter)
2009 Surly Crosscheck (stoker's road bike)
2007 Giant FCR2W (stoker's commuter)
1980's NOS Legnano (stoker's toy)
1970's Stella rebuilt as fixed-gear (captain's toy)