WhineConnoisseur

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!

Kerry392

What about Montreal? My husband and I went last Christmas and had a blast. I think it would be perfect in October.

ingridshawn

If you want to plan it before it gets too cold, Montreal would be great. It is beautiful and most of the B&B's like children (as long as they are behaved); another option would be upstate NY. There are lots of quaint towns in NY which offer not only apple and pumpkin carving, but also wine tours, carriage rides, etc. Cooperstown has the Baseball Hall of Fame.
New England is soooooo beautiful in the Fall I doubt you will be disappointed where ever you go.
Best of luck

cantstayhome

Since Boston is my town and I've got a kiddo (just turned 2), I would definitely recommend it! If you want to get out of town for a couple of nights, you could do the coast. Rockport, Gloucester, Salem are all options. You could also do day trips to those locations.

Some of my favorite fall afternoons have been spent in Concord and Lexington. Not exactly a top vacation destination, but a place that seems to fill your criteria is Andover. Cute little town with nearby orchards, pumpkin patch options, some shopping and endless light hiking trails.

As for hotel recommendations, not really sure as I live here, so not much need for hotels. I have taken my son to breakfast/brunch at the Colonnade hotel (Brasserie Jo) and never felt that he was unwelcome. It is a noisy place - may not be the best pick for dinner, but that depends on your kid. There is a mall across the street with numerous restaurant options (as well as many others that are not in the mall).

Also, Boston is a great place for the wee one if the weather does not cooperate. The Childrens Museum and Science Museum come to mind. My son has enjoyed the MFA, as well. If you end up staying on the coast (north shore) there are quite a few indoor playground options, too. I'm sure there are some south, but I just don't know them.

Be aware, however, that Head of the Charles is the third weekend of October and the city fills up for the event.

Good luck!

cantstayhome

Could also do a Cape/Boston trip. There is a resort in Hyannis, I think, that is supposed to be a great place for kids. Great indoor pool area. Can't remember the name, but I'm sure you can find it here.

Underhill

The area around Concord would, I think, be very nice. Concord itself has a very nice downtown segment, and you can visit the Louisa May Alcott house and the serene Sleepy Hollow cemetery, where some of the great names of American literature are resting. We stayed at the Concord Inn, which was very nice.

Another excellent choice would be Longfellow's Wayside Inn, in Sudbury. There you can visit the schoolhouse where Mary's little lamb followed her, and there's a working grist mill. Lots of beautiful countryside, too, and the food at the Inn is terrific: classic American. Oh, those corn muffins!