Looking for a couple of routes for a VT Backpacking trip

Hi there,

I used to be an avid backpacker but it's been many years.  I'd like another go at it this summer.  I'd like to do a 2 day (overnight) trip as a trial run, then a longer, 3 night/4 day trip.  I'm interested in VT.  I'm in reasonable shape and would like to challenge myself a bit, but I also think I should take it slow and go for an easy to moderate route that I can enjoy.  

What are your thoughts/ideas about trails/loops I could take?

Thanks much.

pick any of the good sections of the Long Trail that have some above treeline hiking - Monroe Skyline, Mansfield/Smugglers Notch area, etc. Very easy to do an overnight on any of sections with shelters/tent platforms in close proximity to where you want to end hiking for the night.

One issue with VT backpacking is that our primary backpacking trail, the LT, is just a single line , with some tributaries leading off to various other trailheads. Therefore its hard to find many loops of of the length you'd want for multiple day hikes. To solve this, you can either use two cars, or stash bikes. Stashing bikes works really well. Then hike any section  of the LT which is quite nice. Or, look at NH which has a lot of nice 30-50 mile loops, and higher mountains which equal less bugs and more views.

The southern terminus of the Long trail/AT in Mass. to RT9 just outside of Bennington is very nice and has public transit into town and back to Mass. (At least they did last year). If 3-4 Day's is more your liking, then continue to Kelly Strand Road, just before Stratton Mt. it's 36.9 Miles and wonderful. Plenty of shelters..although with Covid it is recommended to Stealth camp (Many area's available for both Tent and Hammock set ups). This route will require a pick up most likely at Kelly Strand Road, as it is remote and the usual hitchhiking is likewise not recommended in covid times. This was my first multi-day on the Long Trail and is a nice intro.

If you want a bit more challenge (And FANTASTIC VIEWS) , then try the northbound route from the Winooski River Bridge to Vt. Rt 108 of the Long Trail , it's around 22.9 miles includes the Mansfield Summit and ends in Smugg's /Near Stowe. More up hill than the first route and a pick up or car spotting would be required. The huts are super nice (Again closed due to covid) and stealth camping might be a bit more tricky.
Have Fun , The Long Trail is the BEST !
If only one car is possible and your solo, consider halving these suggestions and reversing your path , back to car !