Being an avid hiker in upstate NY, I'm familiar with the area. Breakneck Ridge is very popular with hikers, so much so that it has its own railstop on the Metro North rail line. Its certainly not an easy hike...The first "stop" on the hike, with appreciable views, is at about 700 feet above the Hudson River. The rocky trail climbs steeply over and around boulders, continuing to the summit at about 1,300 feet. The entire trail is about 5 miles long, but the climb to the summit is only about 3/4 mile (its that steep). And yes, there are plenty of opportunities to fall great distances at several points along the trail.
Breakneck Ridge is located near Mount Taurus (also known as Bull Hill). According to local legend, the Taurus got its name from a bull that was chased by farmers until it fell to its death from Breakneck (giving both mountains their names.)
Rt 9D passes right by the base of Breakneck Ridge, and in fact passes through a short tunnel which bisects the Putnam/Dutchess county line.
Rt 9D can be followed south to Rt 9, which parallels the Hudson River all the way south into Manhattan. Followed north, Rt 9D intersects I-84, which travels east-west (west through Newburgh NY and into PA, east into CT).
Weather reports indicate the temperature on the 12th (a Friday) topped out at 60 degrees, with just over a half-inch of rain recorded for the 24-hour period. The weather on Saturday remained around 60 with only a trace of rain recorded for the day.
My first thought on that date was that it would have been Columbus Day weekend, but that actually occured the previous weekend (being celebrated on Monday the 8th).
The victim seems to have been appropriately dressed for a visit/dayhike to the area, though the choice of an umbrella over a rainsuit might indicate a lack of familiarity with the trails (if she indeed were there hiking). Holding an umbrella on those rocks, especially when rain-slickened, would be courting disaster. She had in her possession a small flashlight, a small compass...Not the equipment an experienced hiker would typically carry, but possibly someone accustomed to infrequent hikes or strolls.
The victim was also carrying several hygiene items, items that one wouldnt typically bring along for just a short outing. Makes me think she was carrying with her whatever she had brought from home...And that she may have been staying at a local hotel or B&B. The possibility occurs to me that she may have had her ID, credit cards, phone, and money (bills) in a wallet that might have been inadvertently left on the train, bus, taxi, or whatever conveyance she took to the trail. (I've seen it happen on occasion, hikers will remove a wallet or small case from their packs to make a cell call, stick the phone in a pocket and walk off without the wallet).
This makes three UIDs found in parks in NY in recent years. The remains of a male were found in Bear Mountain State Park in 1991; and remains of another male were found in Sterling Forest State Park in 2005. (All of which I've hiked...Ive learned to keep my eyes open).