There are no "big" cities in Vermont. Our biggest city is Burlington, which is only 50,000 people.
If you are driving to Montreal from NYC via VT, there are two basic ways to travel: up Interstate Highway 91 from Brattleboro to White River Junction, connecting to Interstate 89 all the way to the Canadian border.....or, taking Vermont Route 7 from Bennington all the way north to Burlington.
Other folks here may have some good alternative suggestions, too, beyond that which I've described here, these are by no means the only interesting places....especially if you want to travel off the beaten path a little bit and see the gorgeous interior of Vermont, towns like Chester, Weston, Rochester, etc.
Woodstock is a great place to stop a while, relax and hopefully you will decide to stay? Depending on which route you are coming up from New York, (I91 or I87?) it is very accessable (I91 is the easiest) and full of history, food and lodging operations and independent stores.
Check out the village web site at www.woodstockvt.com and see everything from a National Park you can walk into (Mount Tom) the museum at Marsh Billings Rockefeller estate and much much more including a covered bridge right in the centre of the village.
The village has the Vermont Hospitality Councils 2007 Restaurant of the Year and 2006 Bed & Breakfast innkeepers of the year located in the centre and also houses 2 of the top 6 Trip Advisor rated B & B/Inns in the whole State.
Chester is a lovely place to stop on route and is only 10 miles from I-91. Chester also has B&B in the tripadvisor top for the state and USA. If your driving by in the next few weeks then you could get to see a new Hallmark Christmas movie being filmed in town with Tom Arnold as Santa Clause!
If you choose the RT7 route to Montreal, the village of North Bennington is a convenient yet rural and quaint stopover, just 3 hours from NYC. Restaurants (casual to fine dining) are within walking distance of 2 out of 3 B&Bs. You can rest & save gas. Also, there is a gas station in North Bennington. If you time it right, there might be live entertainment in the evening sponsored by the Vermont Arts Exchange at the old Sage Mill.
The most direct route from NYC bypasses VT, going straight up the NY Thruway, Route 87. Rt 7 in Vermont is a pretty, but slower 2-lane road with a 50 MPH speed limit. If you want to visit Burlington (a very pretty little city with a nice music and art scene), there are a couple of ways to go:
1. Drive up Rt 87 in NY to Port Kent (a bit east of 87), and take a ferry across Lake Champlain directly to Burlington. The ferry takes ~1 hour & is very pretty during the day (in nice weather).
2. Rt 87 to the Lake George area in NY, then take Rt. 149 to Rt 4 to Rt 22A to Rt 7 to Burlington. This is the most direct route. Driving time from NYC to Burlington is ~6 hours.
3. From NYC, go east thru Conneticut (I can't recall the road, but it's obvious on a map), then I-91 to I-89 to Burlington. This is a nice scenic highway drive all the way and takes ~6.5 hours. If you want to see Stowe, it's on the way, about 20 minutes' drive off I-89, ~30 miles prior to Burlington.
You'll find lots of information on things to see and do in Burlington (or Stowe, Woodstock, etc..) by doing a few searches in this forum.
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