...prize included two plane tickets to anywhere in the lower 48 and a $500 hotel voucher...
Unless you can easily afford to add a lot of your own personal funds to this, it would be crazy to squander such a modest budget in a big city or popular tourist destination.
Instead
look outside the box, perhaps a charming, affordable bed and breakfast arrangement; cycling through scenic areas unlike your normal day to day surroundings; day hikes or short backpacking excursions; rented rowboat rides; photographic opportunities... something where you can make the most of available funds. Consider areas seasonally out of current favor.
Whatever you decide on, make memories and enjoy the hell out of it.
