I don't know if there's anything in particular going on, but it's a nice time to be in the Hudson Valley, which is very close to you. I'd go there, perhaps staying in a nice B&B in the Rheinbeck area. There are some great restaurants all over the area, though I know the area around Hudson the best (it's about 25 miles north of Rhinebeck) and probably closer to you.

But for that kind of money, you could come to NYC for a couple of nights in a nice hotel.

You could look at Sagamore on Lake George. Foliage this weekend should be perfect. I'll be up that way for a long bike ride around the lake.

Setting is beautiful. If weather is nice you could still go out on the lake in a boat (power, canoe, kayak). I can't speak to the quality of restaurants in that part of Lake George.

It's about 2.5hrs from Danbury to that area.

Since it's foliage season, you may have a hard time getting someplace in northern New England, but look at Woodstock Vt, Lyme NH, and other small towns in NH & Vt. If you want a more urban, somewhat European feeling destination, Montreal is fabulous.

It's already gorgeous here in NH. The Warner NH Fall Foliage Festival will be this weekend. Sort of old-fashioned. Parades, craft fair, farmers market. Last year the Warner food tent was all local food. The organizer did a fantastic job. Most upscale might be the Centennial Inn in Concord. I haven't eaten there nor stayed there (too close to home). Concord restaurants aren't too bad but you would do better in Manchester except Concord has a nicer downtown. The Concord location also puts you close to I89 for a quick trip over to VT and the towns zootsi describes. I would try not to be on the road southbound on Sunday afternoon but keep in mind you can take some alternate routes to NW CT such as going west to the Keene NH/Brattleboro VT area than south on I91 which should be a pretty ride.

Thanks all for your responses.
After looking at the weather report we are sad to see its going to rain most of Sunday.
Thinking of spending two nights in NYC, although we aren't necccesarily city people. Looking for suggestions for a romantic itinerary.

Along the Hudson to Sleepy Hollow( Tarrytown NY) Leaves, tours and Scary...

Look at the Watch Hill Hotel in Watch Hill RI

The OP has started a new thread about traveling to NYC.

emalloy are you thinking of The Ocean House which was recently rebuilt. Interesting back story and project

http://oceanhouseri.com/about/history/

Good suggestion, and you could explore Mystic/Stonington area

Exploring Tarrytown/Sleepy Hollow is great this time of year. You could drive up Bear Mountain/7Lakes Drive, explore one of the estates, go to one of the CIA restaurants, check out a band at Tarrytown Music Hall.

http://www.hudsonvalley.org/events

There are some beautiful places to stay in Lenox and the Berkshires, drive up to Mount Greylock, have a picnic on the grounds of Tanglewood, explore Great Barrington.

http://www.mass.gov/dcr/parks/mtGreylock/multimedia.htm

The Paradise City Arts festival is this weekend in Northampton MA. You'll find plenty of top-notch restaurants, too. But I can't think of any hotel that expensive around there.

For a destination resort hotel, check out the Mohonk Mountain House. I've always wanted to stay there -- foliage should be gorgeous this weekend.

The Orchard-Williamstown, MA

Lookin_Glass, yes it is the Ocean House Hotel in Watch Hill, RI. I think they might have rooms that are close to the price the OP indicated and it is a beautiful location.

Ok, so we went totally off the wall. Vermont and the leaf peeping areas seemed so busy, and NYC was so expensive and the truth is we are just not really city people ... so we decided to go the other direction.
We are booked for Long Island Wine Country. Wish me luck (and if anyone has been suggestions!)