Ride suggestion from NYC
 

Hi everyone, I'm new here and have a question. I have six free days soon from work and want to go on a camping ride by myself from NYC. Ideally I'd like to go as far as possible and then take a train back on the last day. I thought of "trying" to cross the border with Canada by taking route 9 as far as I can go. But then I thought that I should ask you guys what are some other nice trips worth doing alone for a few days.
I know it all depends what pace I'm looking to establish and though I cycle a lot I'm not a racer.

How many miles do you want to put in a day?

I would consider heading up to the Catskills and onto the Adirodacks. You could easily spend three days in the Adirondacks. No sure about the trains getting back though.

You could ride up to Ward Pond Ridge or look into Fahnstock (may have been renamed). I think Fahnstock has camping. Look into Bear Mountain. You may need a train pass for the Metro North Train (i think they are free). Keep in mind that not all Amtrack trains have baggage cars for bicycles, so coming back by train from Canada may pose a problem. You could take the North & South County trails as far North as possible, and head east towards Southbury Ct to Kettletown State Park for camping

The amtrak from the adirondacks that I took in the summer a while ago (before I had started biking and when I was about 7) had a lot of space for bicycles. Then again, there was a tour that weekend and most of the bikes stored seemed to be from people who knew each other, so it may have been a party thing. You should be able to just call in advance though,

We had friend​ vist last summer who did a solo tour. He didn't camp but stayed in various B&B's. He took the LIRR from Bayshore where he was visiting and met us in the city. We escorted him from Manhattan to Haverstraw where he spent the night in a B&B. From there he crossed the Bear Mt Bridge and stopped in Rhinebeck. Day 3 took him to Hudson NY. Day 4 into the Berkshires in Mass. Day 5 into Connecticut. Day 6 the ferry from Bridgeport to Pt Jefferson and back to Bayshore.
If you plan on camping the NYS Parks website can give you list of NY campsites. Camping - NYS Parks, Recreation & Historic Preservation
A train pass good for both Metro North and LIRR is $5