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When I lived in Manhattan, would occasionally go to the Cold Spring Depot in Cold Spring. Take the saw mill or taconic north and then head west. Could come down the NJ side on your way home depending on where you are in NYC. Lived in NJ for almost 10 years now, but a quick Google indicates that the restaurant is still open with good reviews.
Not sure we're you're at in the city, but there are amazing driving roads on the both sides of the river, so it's hard to chose, excuse the starting point. I'm biased to Northern Dutchess/Columbia county roads personally -
Nicest lunch also IMO is the Golden Russet -
You could also cut out the northern route towards Hudson and coming back down and just come through Kingston, that would save a considerable amount of time depending on how far you'd like to drive.
If you're looking to go that far north, there's some great roads near Mohonk Mountain (new New Paltz).
Someone sent me this once.
Starting from Warwick Ny take 17A to RT17 (17A ends @ 17)stay straight on Rt106 (this is Harriman State park a very windy road caution lots of hikers and bicycles and park police are strict) continue to traffic circle 3/4 around circle take Seven Lakes Dr north to Rt6 west follow signs to I 87 North to I 84 west to Rt 208 north through Wallkill (note in Wallkill there is a Stewerts shop that has non-ethanol gas) continue on 208 to Rt 44/55over Mohonk Mt to Rt 209 / 55 west follow Rt 55 to to RT 97 ( Sholola ) take RT 97 South along the Delaware through Hawks Nest and on to Port Jervis. From there the best way home for you is probably I 84.
As in, Long Island? Nah. I would not come TO LI for roads. Too crowded here. And while there are some nice droves around the North Shore, those wealthy areas are also heavily patrolled by their own police departments who don't take kindly to non-residents speeding through their expensive neighborhoods.
That corner of NJ north and west of 94 all the way up to High Point. Lunch at Buck Hill Brewery. Return on 80.
Play up and around Vernon, NJ. The roads have more elevation changes than turns, but some beautiful scenery. Lunch at Crystal Springs or any of the many local spots.
Avoid Bear Mountain! Unless it is 10a on a weekday, Bear Mountain is loaded with bikes, pedestrians and the necessary police. Tuesday around 10a and you are good to go.
Not going to give out my best drives. Though, I will hint that water tends to make nearby roads interesting.
If you're looking to go that far north, there's some great roads near Mohonk Mountain (new New Paltz).
Someone sent me this once.
Starting from Warwick Ny take 17A to RT17 (17A ends @ 17)stay straight on Rt106 (this is Harriman State park a very windy road caution lots of hikers and bicycles and park police are strict) continue to traffic circle 3/4 around circle take Seven Lakes Dr north to Rt6 west follow signs to I 87 North to I 84 west to Rt 208 north through Wallkill (note in Wallkill there is a Stewerts shop that has non-ethanol gas) continue on 208 to Rt 44/55over Mohonk Mt to Rt 209 / 55 west follow Rt 55 to to RT 97 ( Sholola ) take RT 97 South along the Delaware through Hawks Nest and on to Port Jervis. From there the best way home for you is probably I 84.
That's starting on Arden Valley which is amazing to drive -
Woodstock, NY for lunch at Cucina
Westchester for lunch at Inn at Pound Ridge
Salisbury, CT for lunch at White Hart Inn / swing by Lime Rock
Kent, CT for lunch and shops
Beacon, NY for lunch and DIA Beacon contemporary art museum
Great Barrington, MA for lunch and shops (up RT 7)