This is a terrific starter trip for anyone wanting to get into multi-day, self-contained touring. It starts with Metro North to Wassaic. First day uses rail trail for first half, then rolling hills with a climb or two over to Hudson, NY - a charming town on the river with very good restaurants, antique shops, a professional theatre and many restored late 19th/early 20th century homes. Second day begins with back roads (including 1/2 mile of hard pack - very doable on road bike) and cute towns, and ends with 11 miles on Rte. 9 past such sites as the Vanderbilt Mansion National Historic Site and the Franklin D. Roosevelt Presidential Library and Museum. From Poughkeepsie, take Metro North back to NYC.
Each day is roughly 50 miles with a little less than 2,000 vertical feet on the first day and about 2,500 vertical on the second day, so not particularly difficult. This trip can easily be done on a standard road bike with a seatpost rack (do not use a carbon seatpost, use a steel post) and a large rack pack; or you can use a medium or large Carradice saddlebag.
When I did this tour in 2010, we stayed at the St. Charles Hotel in Hudson. It’s not elegant, but we were able to keep the bikes in our room, and the hotel is in walking distance of downtown and excellent restaurants. There are several B & B’s in Hudson, but they are considerably more expensive.
GPS links: https://ridewithgps.com/routes/33504105 Day 1
https://ridewithgps.com/routes/33504091 Day 2
cw 11/20/13 Rev. 7/2020