it sounds like a great getaway! i don't know southwest or any seat tricks or even how far connecticut would be, but everything i see and read about your TSA is super strict and specific (and before we were married and visited the US, DH and I were randomly selected on each internal flight for a special search; we felt so welcome and only wished we could be that lucky with the $ kind of lottery) but the weight limit thing is always weirdly lacking in US travel advice- i don't understand how they can be all 'if you can cram and carry 100kg in your certain sized bag, all good', surely if everyone packs an elephant, the plane wn't get off the ground. Anyway that's so not the case here - weight limits on carry-on are possibly the strictest thing here apart from liquids (i can't remember US specific liquid stuff b/c ounces don't compute mentally for me and i don't know if you plan to take paint with you but obviously that's a liquid) but we're used to weighing bags and keeping a buffer because the scales aren't always calibrated great (there was a NZ airport article by a journalist recently comparing the same bag at various 'check your bag weight here' points in one of their airports, and then the extra one at the gate that is the point at which they'd tell you 'nope it's too heavy, that has to get checked, pay for a checked bag now', (which is around $AUD70) and none of the scales measured the bag the same but what they say at the gate is just how it is sadly. Our next booked flights are 5kg in one carry-on bag only, no personal item so it's really limiting but ok back on track ....
like everyone said a refillable water bottle is a must - i would add to that one with some kind of handle you can carabiner to your bag ideally so it doesn't fall out of a pocket, or so it takes up less space if you don't have a specific waterbottle pocket on your bag (hope that makes sense). I love my camera bag but it doesn't have a dedicated waterbottle pocket, but carabiners clipped to the side come in handy to attach like your jacket to as well (through the hangy loop most jackets have around the neckline) if you take it off at the airport or on the plane, it stays with your bag, no risk of falling off if you just placed it over it while you check your phone or under the seat etc.
Wearing layers including a scarf that can almost double as a blanket is the only other thing because it always feels super cold to me with the plane aircon but i imagine it's Fall there so you're already dressing in layers. That also means if you have a jacket with decent pockets, if you need to take some of the weight out of your luggage, you can potentially 'wear it' while boarding by putting them in your pockets, depending on the item.
Happy creating!
) Are there any traveling tips you guys have for me? I just know my suitcase is going to be overweight, so I'm not taking my shampoo/conditioner/soap stuff and will just use what they provide at the bed and breakfast. I'm also going to leave my hair dryer home. {gasp} My hair ought to be a crazy curly hot mess all week. 
