Dearest fellow travelers, I need your advice. Yes, instead of me imparting pearls of wisdom to you, this time I’d like some insight from your fine selves. This fall, my sisters and I are going on a weeklong trip, but we have no idea where to go.

We were meant to meet up in Portland for an event and travel around for a bit, but the event got canceled, so now we’re not tied to any specific location and we’re thinking of going somewhere less expensive to get to. When we realized we had the whole US of A to choose from, we got a little overwhelmed. I’ve traveled to at least two places outside of my state every year since college, but on each of those occasions, I was visiting someone for at least part of the time. The last time I traveled anywhere just because it looked like fun, and not because I knew someone who lived there, was in 2002, when my boyfriend and I drove to New Orleans for spring break our freshman year of college. (Side note: we were so naive and law-abiding that we didn’t even try to buy alcohol, although clearly we could have walked down the street with a giant margarita in each hand and no one would have blinked.)

If you could go anywhere in the US east of the Mississippi for a vacation with beloved family members, where would it be and why? If you’ve already been to great places and have tips on why we should go there, share that too! Drop hints, links, places NOT to go, etc. in the comments below.

Here are the requirements:

• Must not be more than $300 round-trip from Chicago, Michigan, or New York in late September.
• Must be gay-friendly.
• Must be east of the Mississippi River.
• Must have a balance of city/country life within a couple of hours’ driving distance (we’re going to rent a car). We’ll need to be able to go to a sports bar, take a hike in some mountains or stroll around a big park, visit a museum or cultural attraction, and relax in a cheap but tasty restaurant. (We have many interests.)

And… GO! Thanks in advance for your help!