wanderer1

No, not really (the casinos).

So the short list is now Lenox/Stockbridge MA, Essex CT, and Newport, RI.

What is "off-season" in the berkshires?

Thanks to the person who suggested Amtrak for Newport. That would be an easy way to do it (I would think) and if it were me, I'd do that over driving.

Does anyone have any thoughts on Chester, CT?

wanderer1

p.s. Which would be better to stay - Lenox or Stockbridge?

persimmondeb

I don't think there really is an off-season in the Berkshires, but my sister went to school in Great Barrington, and I would find myself there at all times of year, so I may have an odd perspective. I have no opinion on Lenox, but Stockbridge is always nice.

djkbooks

There are more places to stay and more shops and restaurants in Lenox. Lenox and Stockbridge are only 7 miles apart.

Edith Wharten's estate and gardens are a fantastic place to visit.

Williamstown is also very nice. The Clark Institute is magnificent.

Rates for accomodations will increase significantly when Tanglewood gets underway.

abigailwest

Playing on emcash's comments... I love quiant little westbrook with the best restaurant no one knows about Cafe Routier. Westbrook also has a terrific little B&B called the Captain Stannard house. And the outlets in Clinton and westbrook have a lot to offer.

china_cat

I think "on season" for the Berkshires equates to when Tanglewood is in session. So I would say the high season is roughly July 4th-Labor Day. Most of the other artistic offerings overlap with this (Williamstown Theater Festival, Shakespeare Company, Jacobs ladder, Berkshires Chamber Music festival, Theater at the Mount).

you might be surprised at how close to equal the driving time is. Driving up to Western MA from NYC doesn't take as long as I thought, when you come up the Taconic. It will be apretty drive for your friend, too.

steviegene

chester is very cute, but very small.
I think your other choices would offer more to do, and more options for shopping, dining, etc.

Bluehour

As others have pointed out, Amtrak does not go straight to Newport, it just goes to Providence or Kingston.

Both have their advantages. Not all trains stop at Kingston, which is a tiny, old-fashioned country station near the University of Rhode Island campus. (It's so scenic, Richard Gere is currently shooting a movie there.)
So yes, it's closer to Newport, but you might actually have an easier time arranging transportation from Providence. RIPTA buses leave from Kennedy Plaza, which is a safe five minute walk across Waterplace Park from the Amtrak station. The bus takes about an hour, right down Route 95. (By car it's about 45 mins.)

Or meet in Providence, have a drink/coffee/meal, the mall with parking is right across the street, right off the highway (95), then go off together. You can also take a ferry from Providence to Newport. It takes, I think, an hour and a half? Leaves from the ferry landing downtown. You'd need to catch a short cab ride across town.

You could probably arrange a car, or pick her up in Kingston (if you go to uri.edu, I'm sure there's a map of transport in the area, maybe even bus and cab information for students and visitors). You wouldn't get lost: Just follow Route 138 between Kingston and Newport.

It just depends on what you're comfortable with.

hipahkkid

Mystic Connecticut is only 110 miles south of Boston (1hr 35 minute drive). It has quaint little shops like Main Street USA but also about dozen restaurants/bars/pubs. There is a Seaport, beaches, etc. There is the Foxwoods Casino 25 minutes in one direction and Mohegan Sun Casino 20 minutes in the other direction. Mohegan Ithink is better, not just for gambling, but for nightlife/clubs/shopping restaurants/concerts/shows/sporting events. There are also 2 Factory Outlet Malls about 40 minutes south of Mystic. One has outlets for stores like Levis/Reebok/Bali/Fila the other outlet is for designer stuff like Versace/Hilfiger/Donna Karen/D&G/ etc.