Driving to Montreal from New York City, presents several choices. The most obvious (and easiest) is to stay on the interstate 87, the New York State Thruway, which goes almost straight north from New York City to Montreal. The 200 miles north of Albany to the Canadian border, the Adirondack Northway section of interstate 87, is toll free. Exits on I - 87 are numbered sequentially and not by distance.
A scenic alternative is the 9W highway with views of the Hudson River, which follows I 87 almost entirely. It's best to avoid the 9W south of Poughkeepsie, however, as it is bordered by an endless string of strip malls. 9D is a scenic alternative as are the Palisades and Taconic Parkways which forbid trucks.
The parkways were constructed with lowered bridges and overpasses as Robert Moses wanted to discourage bus loads of immigrants from visiting the state parks.
Stopping in the Hudson River Valley is an absolute must. The following recommended sites are all within a one and a half to two hour drive from New York City (three + hours to Montreal) and are easily accessible from the routes mentioned above.
Kingston, NY, the state's first capital, and site of the largest Dutch settlement in the state is at exit 19. The historic stockade district is well worth a walking tour, which can be completed in an hour or less. Highlights include the Dutch Reformist church (open on Sundays) and the beautifully preserved Hoffman House Tavern. With its intimate stone and dark wood interior and pretty garden terrace, the Hoffman House Tavern is a good lunch stop.
Beacon, NY is home to the 300,000 square foot DIA Galleries that houses a huge collection of contemporary art from the 1960's to present day. Highlights include permanent works by Richard Serra and temporary exhibits of Sol Lewitt's drawings. The naturally lit space is a reclaimed Nabisco factory.
Art lovers can check out the big names in contemporary sculpture found at the Storm King Art Center in Mountainview, off 9W. Most of the large works are outdoors and can be seen from a guided trolley tour. The Edward Hopper house in Nyack is worth a peek, though none of his works are housed here.
Architecture fans will want to check out the Greek Revival church dating from 1835 that overlooks the Hudson in New Burgh. The Boscobel House, in Garrison, just off 9D, is a good example of the Federal style and makes for a pleasant visit and picnic with great views of the Hudson. The ample grounds also host concerts and Shakespearean theater.
Just outside Poughkeepsie, stop at the C.I.A. (Culinary Institute of America)for a meal and a tour. Reservations are recommended at their French and American fine dining restaurants. The new Marriott Courtyard 15 minutes away makes a good overnight stop. If it's good enough for Dick Cheney...
For overnight or day visits, nothing beats the Mohonk Mountain House outside New Paltz in Ulster County. The inspiration for "The Shining", this "house" is more of a castle complete with spa, glacial lake, forested hiking trails and a tricky nine hole golf course. Private balconies and wood fireplaces complete the getaway.