Because you’ll be on trail for a few weeks, you won’t be able to carry all your food at once – you’ll need to stop and resupply periodically. Most people resupply 4-6 times, but there are a decent amount of road crossings and opportunities to get into town along the trail. So resupplying often can be easy if you want to cut down on food weight in your pack. Just be aware that town stops can be expensive and tend to take a lot of time. You’ll need to balance the convenience of carrying less food against the time it takes to make stops.
You can resupply by mailing boxes ahead of time to a post office or a place in town that offers to hold boxes for hikers (like a hostel), having a friend or family member meet you at road crossings with fresh supplies (hikers who travel with a dogs often choose this option), or getting a ride into a nearby town for the grocery store. If your resupply plan involves mailing packages, you’ll want to ship them well in advance to make sure they arrive in time for you to pick them up.
If you’re mailing your resupply boxes to a post office (make sure the PO in your target town accepts general delivery), this is how you’ll want to address your box:
c/o General Delivery
Town Name, VT 01234
Arriving By: ETA
It’s also a good idea to write your name or put a special marker (like colorful doodles or stickers) on all sides of the box to make it easier for postal workers to find it amongst the hoards of other boxes.