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Stay inside Dulles - it's not worth the possiblity of missing your connection (due to sudden long lines to get back through security or inability to get a cab in time, etc.). Buy something to read, have a meal at one of the previous posters' recommendations, and enjoy being relaxed vs totally stressed out trying to get back into the inner security sanctum!
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I wouldn't risk the departing flight. Dulles has been improving the options available. Below is a link to a more complete list, but there's Harry's Tap Room, Gordon Beirsch, and Matsutake. There are a couple of others on the list I have never heard about but sound like they would be interesting to peruse on a layover.
http://www.ifly.com/washington-dulles-international-airport/shops-stores
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re: Dennis S
I'm one of those guys who always arrives way too early for his flight.
Matsutake Sushi on Concourse A serves food court style, but the sushi chef is very good.
Vino Volo at Gate C3 is a high-end place, always packed with first-class type passengers.
Gordon Biersch at Gate D12 is not a fancy atmosphere but the menu is great.
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re: GraydonCarter
Vino Volo was closed last time we were there, but it must have been a temporary thing because IAD is still listed on its website. In that case, I'd recommend it to the OP with the caveat that my judgment might have been clouded by a flight of champagne prior to a Valentine's Day trip to Paris. :-) It's not cheap, though, but you know, nothing in an airport really is.
And I'm with the others, don't bother trying to leave.
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The timing will indeed be tight. Herndon/Reston might be your best bet. Hama Sushi is decent and has the benefit of being fairly fast and right off the toll road. (2415 Centreville Road Herndon). Reston Town Center has a Ruth's Chris, a Morton's, and the outstanding Passionfish. You would need to let all 3 of those know about your time constraints.
Dulles has improved its security lines tremendously, but I still leave myself a good 90 minutes thanks to some hour-long security line experiences.
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