I visited some friends near Ithaca a couple week ago. I took rt 23 almost the whole way there. I live just south of rt 23 near the Van Winkle Bridge. The Rip crosses the Hudson between Catskill and Hudson. FRom the river you can go east through some farm land into Massachusetts. Right on the NY/MA boarder is Bish Bash Falls. A waterfall worth a stop on a summer day.
From the falls you can take rt 23 into Great Barrington. A cool little Bershire town that offers good food, a movie theatre and cute little B&B's that are right up our alley. Bizen Sushi is one of the best sushi places east of Japan (I'll right a separate post about them later).
If you take rt 23 east over the Rip Van Winkle you head towards the Catskills and Windham Mountain.
On the way are a couple of vista points you can pull off into as well as the Point Look Out Inn and Rose Restaurant. On a clear day you can see five states New Hampshire, Vermont, Mass., Conn, & NY.
Continue east and you keep heading up into the catskills. roads there can be a little rough in spots, but its nothing that should deter any rider. Coming out of the catskills you enter farmland for the most part. This section is my favorite. It has long swooping twisting with straights that invite you to crack the throttle. Rt 23 winds through little country towns. there is a really great army navy store somewhere out there too. The road head up and through Oneonta. It crosses US 84 on Oneonta's outskirts and heads back into farm land. From here you can pick up rt 28 and head into Cooperstown. Home of baseball hall of fame and more importantly Omegang Brewery.
RT 23 continues for another 50 miles or so from Oneonta and ends on rt 26. you can take rt 26 south to US 81. I was headed for Ithaca so I took rt 26 south to rt 41 north towards Cortland.
All in all rt 23 offers some good and varied riding. It is in pretty decent shape and runs from Great Barrington, MA west for almost 200 miles to the center of NY. It has a lot of off shoots into the Berkshires, Catskills and farmland of south central NY.