This one will likely be split up. The initial plan was to fly to Detroit for a Tigers game then drive through Canada to Niagara Falls. From there, I hit Presque Isle (Lake Erie) and Cuyahoga NP on the way to Cleveland. I'd see a ballgame there as well as the Rock n Roll HOF. After all that, I would drive back to Detroit for a flight home. Definitely a bucket list trip.
Trip 1- My mother lives in Pittsburgh, PA and I'm looking for any excuse to come for a visit while she is still relatively healthy. I "might could" swing it next month. If I fly to Pittsburgh, the airport is west of town and just 2 hours from Cleveland. If it's a night game in Cleveland, I should have time for both the RNR HOF and Cuyahoga NP on the way up. There is also the Pro Football HOF in Canton, OH but I've already been there. After my Cleveland adventures are over, it's 2.5 hours to Mom's place. Since I'll have my rental car, I won't have to worry about her driving to and from the airport to pick me up. If the weather is questionable, I can flip it and see Mom first.
Trip 2- Pittsburgh is less than 4 hours from Niagara Falls, which is closer than I thought. Presque Isle is on the way and I wouldn't mind doing a Buffalo Bills stadium tour as well. I can't expect any surf in the summer but I might get lucky. I can simply walk across the pedestrian bridge to Canada for better views of the Falls or I could go deeper into Canada with my car. Hamilton is less than an hour away and I'd like to see another CFL game. London is about an hour and a half from Hamilton. The only negative is that it's a long way back to Pittsburgh from there. Hamilton is probably as far as I'd go.
Trip 3- Fly to Detroit as planned for the Tigers game but this time, I have some flexibility. I do not cross the border into Ontario but that's okay. Last time I used that border crossing, my entire car was searched. I was pleasantly surprised by the beaches in Chicago and I've heard that the ones in Michigan are even better. The North Coast is an underrated summer destination. It's about a 3 hour ride from Detroit to the Lake Michigan beaches and I can flip it based on the weather. Unfortunately, a stop in Pittsburgh would probably be too far.

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