« on: August 21, 2013, 01:48:37 pm »
Check out the Atlantic Coastal Route, which goes across the new "Walkway on the Hudson" bridge but used to go across the Mid-Hudson Bridge, between Lloyd, NY and Poughkeepsie. Then moseyed north towards Rhinebeck before turning east towards Millerton, NY. You could certainly use the Atlantic Coastal Route to get from Red Hook which isn't far from Rhinebeck towards Great Barrington. If you don't want to go south and then east, you could certainly use google to find a good route east, the roads once you get north of Poughkeepsie will get a lot more quieter... You could simply take 44/55 towards Amenia, NY and hop on the Harlem Valley Railtrail north to Millerton and then use SR22 towards Hillsdale since there is a section on unfinished trail between Copake and Millerton (I think, unless this has changed). From Hillsdale, you can simply take SR23 past Catamount Ski area into GB. There is a nice hill to climb but its certainly doable and it's easier than trying to cut through Bash Bish Falls into Mass.
Going across Dutchess County will be hilly but doable and nice. Great Barrington downtown, you will find parked cars and 2 lanes in each direction which might have moving traffic at rush hour, but there are backroads to use. If you have time in GB, check out Soco Creamery for some good ice cream and the big candy store, as well as Baba Louies for good sourdough pizza. Lots of good places to eat in GB too...