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I would have loved to have time to get a ride in like that!!
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The hard part is just commiting to do it. The rest is details. It requires a little planning, perhaps some begging and wife bribery (ok maybe more than 'some'), but in the end it comes down to making the time for it. You don't even have to go far. I went on about 3 excursions last year; two were simple day trips. Grand Manan was the only 'overnighter' and none required me to go farther than about 2-3 hours from home.
It's amazing the stuff you can find in your own backyard if you're looking. I hear the cruiser crowd talk about the 'Freedom of the Road'. Nowadays you're not going anywhere on a Harley, Goldwing, etc... that you couldn't take a minivan. Dual-sport is the real freedom of the road because it allows you to leave it. Now with the Chinese DS bikes its affordable for the masses. You see a trail/path/road, you take it. It's amazing the trails we pass everyday on the way to work that we haven't explored.