I know a thing or two about Hudson river crossings over my 42 years of driving. I've waited in jams on the G Dub & Tappan Zee bridges to choking on fumes in the Lincoln Tunnel, I don't want to think of how many times.
BUT, by far the most enjoyable and ironically the shortest Hudson River crossing is the Bear Mountain Bridge. The surrounding area are wonderful vista up and down the river, nice Hudson Valley "mountains" with precipitous cliffs to the river below. There's even a lookout on the Westchester side to look at MORE. Cause that's what New York is about... more.
Regardless of which direction you are traveling, the Bear Mountain bridge kinda, dumps you in the middle of nowhere and unless you know where you're going, there's a distinct likelihood you'll get lost. Oh, yea... your iPhone GPS will help, sure. Not so fast Martha, you have found the only place (save Armonk NY) where cell service stinks. SO, pick your poison until it kicks in and turn around casue you went the wrong way !
The bridge was built privately way back when and if you drive past the "Toll House" that's where they collected your toll to cross it. The Bear Mtn bridge is also located next to the Bear Mountain state park and Lodge, a charming throwback lodge with restaraunts and even a tapas "bistro", such as it is. Christmas and Thanksgiving dinners must be experienced for the fare and fantastic memories, I know, I've gone there since 1959 as a kid and it never, NEVER gets old. The lodge also has one of the biggest Fireplace you will ever see on the 2nd floor bar area, it's worth it for a nice hot tottie and take in the views .
There are piles of hiking trails in and around that area and other okay restaurants and up the road in Cold Spring some outstanding dining.
This part of Not-so-upsate is 25 miles from the city (if that) and easily an enjoyable weekend to explore the surrounding area (and leave Woodbury Commons for a more self loathing experience). This time is for a nice "Adirondack" type adventure without driving for 6 hours.
The Bridge ? yep the bridge is cool. read more