hi - we're in our late 20s, looking for a town with a funky artsy atmosphere, and a nice (not cheesy!) bed and breakfast to stay as we spend some time outside, roaming town, hiking, checking out the leaves. any suggestions on locations/places to stay (mid october)? many thanks!

Are you looking for anywhere in the US, or did you have a particular state in mind? Though you may have selected a state "search category", all the posts dump into the US board with no state attached, so it's difficult to tell.

If you're open to anywhere, check out Saugatuck, Michigan.

ooh sorry to leave out that major detail - we're looking in new england (a weekend trip from NYC)

Awww you sweet young couple!!
How about Rhinebeck? About 2 hours north on the Taconic, apple picking, B&Bs and and old Inn (The Beekman Arms) which also has huge four poster beds and a fireplace..cozy and romantic. A good French restaurant across the street. The Vanderbilt Mansion not far away for long walks on the grounds and a picnic if you wish.
Drive to Hudson NY and do some antiquing.
We used to do it every single Oct..brought home tons of apples and pumpkins, sigh, I miss NY

Have you considered Northampton, Mass.? There is more to the town than the college, but Smith helps mold its aura. It has more than its fair share of art, funk, dining and atmosphere. The town is postioned well for a quick getaway from NY and is within easy reach of the Berkshires, VT, Deerfield, Hartford & environs.

The Northampton area is stupendous when dressed in autumn colors.

You guys are spot-on...I've considered both Rhinebeck and Northampton. Not sure where would be good to stay in Northampton though - any suggestions??

Have you looked at the Red Lion Inn -- Stockbridge, MA.. A real Norman Rockwell type place.

Sorry, this is where the research branches out to you, and you alone. Being from NY as you are, I assumed you knew advance prep was to be expected in New England during prime foliage season (mid October, you state). People from the four corners of the earth will descend upon the area in a good year (which this is purported to be).

This is 02 October, start calling around and emailing to see if anything in the way of good lodging might still be available.

As an alternative, if you miss peak season (surely within the next three weeks) the "after-season" until early November can be pleasant and way less crowded. There will be remnants of the colors and still that good fall-feel.

Good luck.

It is a bit late, especially if you were thinking of Columbus weekend. Here are a few older threads with some more ideas

http://www.fodors.com/forums/threads...1&tid=34528190
fall foliage in Hudson Valley

http://www.fodors.com/forums/threads...1&tid=34511101
suggestions for a long weekend in New England

http://www.fodors.com/forums/threads...=1&tid=1323436
fall colors in NY (dates from 2001)

The Weathervane Inn in Egremont is worth trying. Nice area of the Berkshires.