Fall Vacation Help-- interesting sm town near larger city?

[BeachBum]

Our 5 yr anniversary is in Mid-October. DH and I decided we would rather do a longer trip with DS, than a 1 or 2 nighter near home w/o him. So I'm on the hunt for something fun!

We typically like small towns with a nice main street, cafes, shopping, light easy hiking, biking etc. DS will be 13 mo and is walking. We would also like to maybe pick apples, visit a pumpkin patch, etc. We just don't have those "fall" opportunities where we live.

I don't need a hotel/Inn with babysitting or kids programs, but I do need one where they are nice to kids and he is welcome at breakfast/dinner etc. I'm not opposed to a kid "resort" I just suspect that will be harder to find?

We've never been to Boston, and it just seems like a "fall" kind of place? I thought somewhere nearby where we could do a couple of nights in Boston, and a couple of nights nearby in a smaller town might be fun. But I am no way tied to that idea.

The only other real stipulation is that I'd like to stick to the east coast/ or south just to keep the flight times reasonable.

Any suggestions--specific hotels/resorts or towns are appreciated!

[boolady]

My DH and I have twice been to Tarrytown/Sleepy Hollow NY the last weekend in October for their fall/Halloween thing called Legend Weekend. Let me start by saying that I am not a "themey" kind of person, but it's also just beautiful, with nice towns to walk in, etc. They always have a bunch of activities for Legend Weekend, and it is really nice- you can tour the cemetery of the church where the Headless Horseman is supposedly buried, you go to Legend readings in the church, and at night, they have the whole Legend thing where you can walk around outside and it's all candlelit, etc. The Croton Dam is nearby, which is amazing if you've never seen it, and there are lots of historic houses in the area you can tour, if you're interested-- Kykuit, the Rockefeller estate, Sunnyside, Washington Irving's house, and Jay Gould's house, which I can't remember the name of at this moment. Sunnyside and the Gould place are near the aquaduct, from what I remember, and you can do some nice fall walking there. You can also drive up to Rhinebeck, which is an adorable town for walking, shopping, lunch, etc. or Cold Spring, which is the same. We just always have a really nice time and have already pegged it as a place we can definitely go with our child when she's born. You see lots of families and kids. There may even be more family-friendly activities that we're not aware of because we've never had reason to pay much attention, until now! :)

This is a link to the main Legend Weekend site, but if you do some hunting, you'll find that there are lots of sites about things in the area. Also, we've always stayed at a B&B in Croton-on-Hudson, but already know we would not stay there with kids. There are lots of other hotels/motels around. Good luck!
http://www.sleepyhollowhalloween.org/legend.htm

[Fairy]

Ok, well, this is off your location mark, but otherwise, you describe Galena, Illinois to a Tee. And it's so close to Chicago (well, far if you're from chicago; close if you're visiting from elsewhere), you can also see my great town! But honestly, you can spend a good chunk of time relaxing in Galena, and around October it's even better. http://www.galena.org/

[overcome]

The Poconos?

There is a huge hotel called Great Wolf Lodge, which is totally geared toward kids. Not only are the rooms kid friendly, they also have a huge indoor water park for hotel guests only.
http://www.greatwolflodge.com/Locations/Poconos/

In additionm, it is 5 min away from Camelback Ski Area.
winter
http://www.skicamelback.com/
summer
http://www.camelbeach.com/

Also 5 minutes from The Crossings Outlet stores
http://www.premiumoutlets.com/outlets/outlet.asp?id=59

Pocono Mt Vacation Bureau
http://www.800poconos.com/
There will be pumpkin patch activities as fall approaches. Plus we are only 2 hours from Philadelphia and NYC.

Good luck!