Might be the wrong time of year to start this, but we often stop at nice little restaurants with outdoor patios. In Maryland, and a number of other states, restaurants can (but don't have to) allow dogs on the patio while their owners are dining.
If you try a park with a dog park, distance would be your friend and short duration would work. Farmer's markets are nice too and the outskirts of a fall town fair. Too late in the season for outdoor concerts, and probably too long for a young dog, but I've done that successfully in the past.
Patton CGC BH
Chief fetch fanatic
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