Let's suppose you're thinking of organising a trip to see your favourite sports team play in another city. Your travelling group includes:
a 33yo who can't drive (but can ride, walk, take public transit, etc)
a 64 yo who has some sight issues (but can drive, walk, ride public transit),
and a 98 yo who loves to travel but has multiple challenges (hearing loss, walks with a wheelled walker, needs to rest regularly, best not to take public transit).
All are avid baseball fans.
The group may also include a 33yo and 64 yo who *can* drive, and 3.5 yo kids. (But those people would not be attending the game; they'd go elsewhere for amusement.)

This summer, your team is playing in: Detroit, Cleveland, New York, Chicago, Baltimore, Anaheim, Oakland, Kansas City, Arlington (TX), Seattle.

You are within 5 hours' driving distance of Detroit and Cleveland.
You are within a 10 hours' driving distance (or a short cheap flight) of New York, Boston, Chicago and Baltimore.
All other locations require a modest-to-expensive flight.
(There are other elements but those are the big ones)

Where would you go, and why? Trip is likely to be an extended weekend visit in the summer/early fall.

I would stay home

Sorry - after my snotty answer, I would immediately rule out Boston. Tickets to Fenway are incredibly expensive and the creature comforts are few. Parking is horrible near ballpark and there is no way 98 year old could navigate him/herself into the stands - no railings, uneven terrain. A wheelchair in handicapped seats is the only way it would work.

Of the other parks that I have been to, Iwould pick Baltimore. Camden Yards, being a newer park is much more accessible and Inner Harbor area of Baltimore is a nice place to visit for a weekend.

But I still might stay home - in my own family trips like this start out with the best of intentions and end up as horrors.

On third thought - this is your first post - I may have just been conned by a troll!

I'd go to Anaheim to see the Angels and how they react when Benjie Molina is announced in the lineup.

Gail, nope, no troll -- sadly we didn't make any trip with my grandmother before she moved into the retirement home (she did continue to go to Cuba with my aunt for a while....). We have, however, done some extended family trips since then.
For instance, I rediscovered the forums when I was researching our upcoming trip to Scandinavia (my parents and one of my inlaws are accompanying us on a cruise with one day pre and post in Copenhagen; we;re staying on for another 5 days to hang out on our own - with the kids).