It’s possible. We take two boys, one with each of us. I take the big (3.75 years) boy on a bike seat on the Surly and my wife takes the little (20 months) boy in the Burly trailer attached to her old Cannondale racing bike. The destination was set by the big boy - the train at the end of the Minuteman bike path. He loves trains. We both have racing triples so getting up the big hill on the way home is possible, though not fast.
The little boy likes the trailer, or at least tolerates it in ways that the big boy never did. The big boy likes to talk and you can’t hear him in the trailer until he cries. The little boy is less of a talker right now so he doesn’t seem to mind. And there is plenty of room in the trailer for toys and food and falling asleep. The little boy has tried the bike seat once and really enjoyed it and nearly fell asleep in the seat at the end of the ride, going up the big hill. We had rode over to Ride/Studio/Cafe. The cafe was cranking with a ride coming in and another going. Best coffee anywhere near my house and it was worth the wait since the little boy was patient.
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