I was the co-director TCT end-to-end for 10 years. It began as a hike, but morphed into more of a speed hike and then a race for some after I was involved with the event.
Unless you're set on doing it piecemeal or on your own, I think the best way to do it is by signing up early enough to get one of the limited available slots for the organized event. That provides much of the support.
The End to End begins at Berry Pond in the Pittsfield State Forest and ends in S Vermont.
How we ran it, the volunteers used to prepare breakfast before sunup and would move your vehicle to the end. You could prepare lunches or beverages and the volunteers would meet along the way for you to pick up your package.
The event is not 37 miles, it's the traditional 29miler that the Taconic Hiking Club has run for decades.
We served hot dogs and beverages at the the N terminus.
I can't say how any of this may have changed.
Tips for hiking/running the TCT: It's a series of ups and downs, ups and downs, from MA to VT. Almost the entire distance you're in deciduous forest and hiking it in spring is best done when the leaves are out as it can hot without canopy. Autumn is a good time, maybe one of the nicest times to hike part or all of it.
A few years ago the Taconic Hiking Club commissioned cartographer Liz Cruz to design a map. Even if Liz hadn't designed the maps for my two books and numerous articles, I'd tell you her TCT map is a beauty. Shows all the side trails, proper elevations, private property and much more. You can use the map to plan an end to end or section hikes. You may want to have 2 vehicles if you're looking to section hike. Depending on section, some of the trails to the hollows (the cols) come from dirt roads that involve car spots or dropoffs.
Berlin Mt, the highest point of the TCT is nearby and one of my favorite hikes.