I think how much one brings back and forth depends on a few things -

1) how much "stuff" one has available and if one has the money available to have duplicate sets of rulers, mats, and
cutters?

2) does one have a "permanent" place to migrate to - or does one need to rent a different space each year?

3) how important is it to have quilting supplies with one?

Start slow and you'll learn as time goes by. I started my very first quilt on a trip to our cabin in N. Minnesota about 5 yrs. ago. I packed the quilt pattern, fabric, rotary cutter & mat, needles, thread, scissors (not the batting as I wouldn't get that far that weekend), and that was probably about it. I mentally retraced my needs for that trip and starting that first quilt. Yup, I was certain I had everything I would need for that trip. Oh my, I forgot to pack my clothes. Thought of it half way through the trip! It all turned out fine. Hubby & I had a few good laughs over that one. Enjoy your 2nd home and your quilt adventures!

We haven't done the snowbird thing yet, but in my mind I see myself piecing and making tops in one location, then sandwiching and quilting in the other. Supplies for those activities would be in that location. I buy most of my supplies online anyway.

I used to go for days in my caravan. I had a bag which contained all my mats rotary cutter and notions and patterns I would needed. Then when I came home anything I had forgotten went in. This bag became my away bag and items in it I felt would never be used came out. Fabric was a different matter. I tried to get each project in some kind of box ( couldn't afford new boxes) with required fabric and pattern plus any essential notion, interfacing etc to complete. Sewing machine had its own bag, full of threads bobbins needles etc which stayed together.
i took time filling the boxes and bags and ended up with a complete second set of equipment which was also useful to take to classes.

I'm not sure where you are going in Maine, but where I live there are 3 or 4 quilt shops within a 30 minute drive and a Joann's.

Although I don't move from one state to another, we live on an island during the summer months (off the coast of Maine) and so I do have duplicates of my regular tools, cutting mat, rulers, seam ripper etc... so that I don't have to transport items back and forth. Since I have less time to quilt in the summer, I have already prepared a few projects that I can work on. I hope you enjoy your road trip. Maine's quilt show is the last weekend of July in Augusta.

I also forgot to bring the extra clothing - that was back in the day when DH and four kids would go "camping" with some of the rest of the family! It was a cold, rainy, miserable weekend - and my boys had to wear their girl cousins things.

I love the stories about forgetting clothes! Before I retired, I got a second machine that is the clone of my original one so I have machines in both places. I also scored a second Arrow table on sale and with a gift certificate at Joann's a year ago that is already up there. I have cutting mats in both places. I left some fabric in Maine. I won't have as much of a dedicated space up there (more company, more often) so I'll need to be more efficient. I'm starting to think that using a few under the bed boxes might be the best way to store fabric and notions etc.
The cottage has been in the family for a long time. We've shared it for quite some time but now own it solely. So now I can have more than just a tote and a machine up there. I'm getting excited!
JMoore, if there was a Joann's in North Conway, I'd be all set! Love the Maine Quilt Show too and am planning to demo there for a friend.
Hopefully our car won't look too much like the Clampett's truck from the Beverly Hillbillies!
Thanks for all of your suggestions. I've been able to empty some plastic boxes to pack up a few projects that are already started.

I have a cottage on the river we stay at most of the summer. I have duplicate mats, cutters, blades etc there. I decided to take just charm square packs, fat quarters and solid yardage to the cottage with patterns for projects. I made two quilt tops last year while working to renovate it. I met other full timers and the quilters packed up their projects in bags and boxes for when they couldn't get to a quilt store. Good luck.

We have a vacation location but don't move there for months at a time, so I just take along the specific project I want to work on while there.

My best suggestion is to make a master list. Keep updating the list with what you wish you had brought along. If you check it while you're packing, those things you know you won't need this time can just be crossed off, but if they aren't on the list, you could easily forget them. I keep my list(s) on the computer and edit out what I won't need before I print it out for packing. I section my list off ... clothes/food/craft supplies, etc. with specific notes of what to take to certain locations, like when we visit DDs.

Enjoy your retirement!

I usually ship fabric or projects down. We fly and just do carry ons. I always end up sending fabric back north. Any quilts go in my carry on. There are such wonderful quilt shops here that I can never resist adding to my stash. Next year I am planning on bringing down an extra machine and my extra surger. Those I will package good and check them in. I have a few outfits that I bring back and forth. Have a wonderful summer!