The answer to “why”? I used to stay at one B&B and venture out to all reaches of Vermont from my home base. Sometimes it was hard to meet up with my VT friends who lived far or to meet a traveling SOV forum friend who was on the other side of the state. Honestly, it got boring for me staying in one place. In the past 3 years, I've actually started inn hopping again and I absolutely love it! It's like an adventure in so many ways. I've met countless new folks, listened to so many stories from travelers from afar as well as the innkeepers' insider recommendations. With more time on my hands, I've been able to explore new areas surrounding my lodging without rushing back before dark. I've also had time to discover so many new back roads, towns and villages that I would not have done if I had remained in one place. And not to mention all the new restaurant venues!
Never knowing what to expect when I reach my next destination is an absolute thrill for me! The unknown basically is my motivation. In retrospect, I've been rewarded with spectacular lodging and many new friends along the way in each of my locales. So, with a lot of boundless energy and a love for the social aspect of inn hopping, this is the “why” part of my madness!
Ahhhh, back to getting ready!
Preparation takes time. I just don't want to forget anything which might take away from my very busy itinerary and time with my friends up there. And, I don't like to be shopping for the basics that I may have forgotten at home! So, starting after Labor Day, the grand uploading of stuff for my trip starts to accumulate in my dining room. (I also have to think about getting it all into my SUV! And it does fit!) When my Vermont friends come and pick me up with simply a dog earred Jimapco and an empty car they are aghast staring at the trunk!
So here's what I do!
●First, one pile is all the things my sweet dog needs for boarding: food, toys, bedding, instructions and contact information of all sorts!
●Second, a pile of my horseback riding gear, hiking shoes, back packs, hiking maps, bug sprays, sunscreen and caps! A case of water. I'm still hoping to get my hiking poles before I leave!
●Third, a large duffle bag containing all my warm jackets, vests, rain gear, hats, gloves, scarf, fleece, etc. for those cold mornings hiking or for a trip to the mountain summits on the lift rides where the weather can be in the 30's with a wind chill! Lots of layering type clothing in this pile! I'm always hoping for colder weather. Sometimes, it's been so warm in Vermont, I never opened the duffle. But I am prepared nonetheless!
●Forth, small luggage with basic clothing for the two weeks.
●Fifth, a small bag to carry my Jimapco, Delorme and Cartographic, and printouts for all my adventures scheduled for the two weeks, laptop and tablet and cords and chargers galore! And a trash bag.
●Finally, a rolling carry on packed with random toiletries and clothes for the next few days. This is all I take up to the inn! I put that at the end of the trunk and change out whatever I need for the next day. I never have to carry much into the inns where I am staying.
My friend looks at the dining room and says, “You're really taking all this? Are you taking the kitchen sink too?”
Does this sound like a lot of work? Maybe initially, but the night before the SUV is prepped and at the break of dawn I'm off! 
When I cross that border into Vermont my excitement builds and that ear to ear smile of complete satisfaction, happiness and anticipation appears! The music is on, my adrenaline is in full gear, my sunroof is open (optimistically hoping for a sunshiny day) and thoughts of autumn in Vermont 2019 take over my soul!
Time to focus on nothing but fun and adventure and fall foliage! Vermont here I come!
(Hmmmmm, did I forget anything?)
I put all my fall decorations out today not only because I am ready for them but I want to have plenty of time in September to focus on my trip. The suitcases came out of the basement and are now upstairs just waiting to be packed. I'm just like you, the more organized and prepared I am the better the trip. My daughter asked me why we cant just wing it. My response was because I don't want to miss anything 
Everyday I find new things to to add to our list. Have to also agree with staying in different locations. Thats what makes it fun! Im most excited about our stay in Woodstock this year!