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Help selecting a moderate difficulty 7 day section within New York, Connecticut and Massachusetts the first week of October

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    • Help selecting a moderate difficulty 7 day section within New York, Connecticut and Massachusetts the first week of October

      I am a new backpacker. What is a moderate difficulty 7-8 day section through New York, Connecticut and Massachusetts? I plan to do this the first week of October. I had planned to start just inside New York, go through Connecticut and end up just inside Massachusetts. I had thought there were mostly 10 mile sections which seems doable for me in the shorter days of the fall. However, I recently read that there are some very challenging portions in Connecticut. Help!

      The post was edited 1 time, last by Counselorman ().

    • Hello Counselorman, welcome to the Cafe.

      I have only done short, weekend hikes in CT. I cannot advise on the entirety. Anyone else?

      One CT section I did had some pretty steep climbs, but they were of a reasonably short duration. No big mountains. Connecticut also has some easy strolling sections along the Housatonic River.

      I would think the hike you are suggesting would be a great section to start, especially if you plan on averaging a ten-mile pace. Where in NY did you plan to start your hike?
      “Of all sad words of tongue or pen,
      the saddest are these, 'It might have been.”


      John Greenleaf Whittier
    • We had a small group of Scouts many years ago that did the whole CT section as a 50 miler (done over 5 days of 10 miles, plus a bit since the section is 52 and you can't exactly stop at the CT/MA line, as that isn't at a road like the NY/CT one is).

      We've also had a few Scouts doing Hiking MB do their 20 mile day hike starting from the CT/NY line, since that allows the end of that 20 miles to be the about 5 miles that parallels the Housatonic (and has a total elevation change of about 100 feet over the stretch).

      There is one fairly steep downhill just before you hit the flat stretch and there are climbs here & there, but given that the leader who was leading/suggesting these hikes was fairly familiar with most of the trail in both CT & MA, I suspect that these were easier sections to offset the longer distance of either the 20 miles in a day or backpacking 5 days straight carrying everything (except some water, which was delivered by a parent due to dry conditions that year).
    • Is a place to park a car or access to public transportation an issue? That might influence where you start or stop your hike.
      That'll be a great time of year to be in that area as the leaves should be in great color.
      CT would be a good first section of the AT to hike and you'd have one entire state finished.
      " I recently read that there are some very challenging portions in Connecticut" As I remember there's 2 challenging parts, Bear Mountain and Saint John Ledges. How challenging is a matter of personal perspective. There are also some great places to camp, in particular I'm thinking of the Silver Springs campsite and a shelter area ( I don't remember the name off the top of my head ) that most people never go to because it's a 1/2 mile down hill from the AT.

      Welcome to the cafe and I'd love to hear how your trip goes in the end.
    • Looking back through my section hiking list, I can offer the following suggestions.

      NY Route 52 to CT Route 341 (Kent, CT) - 3 days
      CT Route 341 to CT Route 41 (Salisbury) - 3 days
      CT Route 41 to Jerusalem Road in Mass - 5 days
      Jerusalem Road to Dalton MA - 3 days

      Note that most of these sections were finished early on the last day. So stringing a few of them together would save a day or two. My buddy and I also had our young boys along for a few of these sections, so we weren't tearing up the miles each day.

      Have fun!
      Trudgin' along the AT since 2003. Completed Sections: Springer Mountain to Winding Stair Gap NC, and Max Patch NC to Carter Notch NH