noknees438 Loc: NYC

Not exactly "nearby" but if you're willing to drive east and west, there's Howe Caverns to the west in NY and to the east there is the Sudbury Inn (aka Longfellow's Wayside Inn), the oldest operating inn in the US in Sudbury, MA. They serve excellent food and good photo ops on the grounds

Cape Codder Loc: Cape Cod

Just on the line between NY and Mass near Copake NY is Bash Bish Falls. It is a not a far hike to them from the parking lot. Spectacular falls and pool beneath them. (No swimming, but wading allowed.

Bartholomew's Cobble in Ashley Falls (part of Sheffield) has a lot of wonderful scenery. Pastures with cows grazing, birds in the woods and fields, wild flowers. Just down the road is the Col. Ashley House (google for times of opening and directions) a house from before Revolution, an interesting glimpse into living in those days and an interesting story of Mumbet whose grave is in the Sedgwick lot in Stockbridge.

Travel down 183 from Stockbridge to Great Barrington. Great views of the Housatonic River. In the village of Housatonic lots of art galleries and fun to just walk around photographing architectural details.

Great Barrington has an uglified business strip on its northside on rte 7 (but there is a wonderful bookstore in the plaza and next to the plaza a super chocolate shop (chocolates hand dipped and fudge whirled up on premises.)
Downtown great Barrington has lots of interesting little shops and is an interesting place to wander and take pictures. The river walk is a short stroll along the water's edge.

South of GB on 7 is another chain grocery store and then what you might call "Antiques Alley" if that is your pleasure. Lots of farm fields and views of the hills, etc.

Have a great time!

bobmcculloch Loc: NYC, NY

Just visited Howe, wide angle, wide open, ISO 3200, still some softness, had to manual focus some times, mixed flash and available darkness, different shots , some better as flash some without, guide there suggests best times and days, Monday thru Thursday, before 11AM or after 3PM, cafe food not bad, didn't stay at their motel but it's right next door.

Hunakai

Bash Bish Falls State Park.

rdgreenwood Loc: Kennett Square, Pennsylvania

Pittsfield is my hometown, so I've been reading this with interest. If you have a clear day, make sure you drive up the road to the top of Mt. Greylock. The view is spectacular. Near Pontoosic Lake, find the amazing Balance Rock and get your snapshots taken. As far as food goes, find Teo's for lunch and order five hotdogs with everything. (They're tiny, so you won't have to risk stomach pumping.)

I haven't driven the Mohawk Trail in many years, but I recall it being lovely. Finally, the Berkshires run north into Vermont, so don't let a border slow you down.

Have a great trip.

rehess Loc: South Bend, Indiana, USA

But do slow down if you drive into VT. Many years ago I discovered by experience that some small towns in VT use through traffic to balance the town's budget

See above.
In 1984, the Town Constable in Plymouth VT managed to ruin my day.

rdgreenwood Loc: Kennett Square, Pennsylvania

1984, huh... You need to put it behind you. That Constable's probably retired by now.

OP, drive carefully and enjoy.

rehess Loc: South Bend, Indiana, USA

No bumper sticker.

The approach to Coolidge's home is on a wide highway, with lots of signs on the left side of the road telling you of an upcoming left turn to get to his home. What they didn't warn of was the stop sign on the right side of the road partially hidden by plants ... and the town constable who apparently spent his day down by the sign (he went back to that spot after writing out our ticket).

soxrul Loc: ct

Rdgreenwood, Pittsfield is my hometown too (PHS class of 1965) and I agree 100% with your 3 suggestions. 5 Teo's dogs is the perfect number.

yrral

Take a walking tour of downtown Stockbridge Mass....Norman Rockwell territory.

rdgreenwood Loc: Kennett Square, Pennsylvania

Alas, I only did elementary school in Pittsfield--Crane, Mercer, Russell--but it's still home. Tell me, should I have mentioned Angelina's?

Buildrt Loc: Sarasota Fl

I'am displaced Vermonter so I'm familiar with that area. I don't know if it's true or not but someone told me that the state has stopped that practice by requiring all traffic violation money go to the state and not the locals. I think it would be good practice for all states to adopt.

rehess Loc: South Bend, Indiana, USA

I have heard that south east states, where speed traps were once the normal way of raising money, have also stomped on that practice, because at the state level they understood that practice was harmful to their tourism ambitions.

In the case I was talking about, we did visit the Coolidge stuff, but then made a beeline for NY and didn't spend another cent in VT. The day before, I had picked up two film mailers in South Conway, NH; I used the one from CT, but I trashed the one from VT.

525erving

Stanley Park westfield

drivered Loc: Capital District, NY

If you are in Stockbridge be sure to have a lunch at the Red Lion Inn. A great place to visit and eat.