NYC to Maine, via Berkshires

My boyfriend and I are planning a summer road trip. We're coming from NYC, where we living in Brooklyn, and hope to end up in Portland, Maine.
His folks have a timeshare in the Berkshires the week we are travelling, so we are planning to stop over there for a day or two (we've been there twice before and love Mass MOCA and one of our favorite restaurants EVER, Nudel, as well as Tanglewood and...well, we love the area!).

Our interests are architecture, food (not volume, but rather really good regional specialties, inovative recipes, farmers' markets, etc.) maybe some beach(! I am the one excited about that!) hiking (glorified walking - not packs!) festivals, concerts, a combo of cheap motels and a few romantic and nice bed and breakfasts/inns.

We're from NYC, so we are going to eliminate anything between NYC and the Berkshires to do on other trips, as well as Cape Cod. Boston can be missed as well. We're looking for cool offbeat experiences, great restaurants and a few nice places to stay.

Any advice? Right now the plan is to drive up to the Berkshires from NYC, then to Portland. Maybe we'll go up to Acadia, but that's not a fixed idea.

Sounds like a winning idea for a road trip vacation, and a nice way to get out of the The City. You did not say how long you are able to be on the trip, and if you were on relaxed or strict budget. Festivals and concerts, as you know, are almost something you have to schedule yourself around. It's rare to be able to arrive at a place and find something going on unless you plan it that way.

Acadia - it's been years since I've been there, but I remember that as being gorgeous. Thunder Hole has to be the one that sticks in my memory.

Anyway, welcome aboard!


Donna

Welcome aboard the RoadTrip America Forums!

Well, the 'obvious' choice for your drive from the Lenox area to the Maine coast would be to take the Mohawk Trail across Massachusetts. Where possible, take MA-2A, the old road, rather than the freeway MA-2. There are plenty of small state forests along there that would offer opportunities for short hikes, including Mohawk, Erving, Harvard, Templeton and Leominster. for something on an architectural bent, make a stop at Gardner Heritage State Park. Around Leominster, you'll want to turn north rather than continue east into the urbanized Merimac Valley (Lowell, Lawrence, Haverford) and take roads like MA-13 and NH-101 to the New Hampshire seacoast and the Portsmouth area. Odiorne Point is another great place to take a hike, and Portsmouth, particularly Market Square and Strawbery Banke is an architectural wonder. Then on your way down east be sure to take as many of the shorefront roads as you can to places like the Nubble.

AZBuck