The big autumn festival here in Garrett County/Deep Creek is 'Autumn Glory' which last year fell over Columbus Day weekend (I think). They haven't announced dates this year on their website but I would guess it's likely the same time. I looked back at my weather station which I installed on Oct. 13, 2018 and highs that month were generally in the upper 40s/50s, with a few days near 60/low 60s. Last October was way warmer, with early October featuring a few low 80 degree days followed by upper 50s/60s around Columbus Day (and some 70s after that). So basically, yes it certainly can feature warm weather here in early/mid October. For awareness, average temps here start in the low 60s the early part of October.
That's probably a long-winded way of saying that yes, Columbus Day on average should feature temps that are warm enough to do things outside (hike/boat/etc) and you could also time it with Autumn Glory where generally foliage should be at/near peak unless we have a warmer fall.
But then again, warm is relative to people - so if you want to have a better chance of warmer weather, do late September. I have some family members that like to b&tch, so I try to keep them happier for my sanity but to each their own
Happy to help with recommendations, etc!