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Late October in Stockbridge - Any Suggestions?

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Dublin, Ireland
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Late October in Stockbridge - Any Suggestions?

My wife and I are planning a two day trip to Stockbridge at the end of October (I know it's not exactly the best time of year, but it's the only time we can travel).

Can anyone give us some suggestions and ideas as to what to see and do? We will obviously be going to the Norman Rockwell Museum, but anything further afield of off the beaten track would be good to hear about. We'll have a rental car, so travelling is not a major obstacle.

Thanks in advance for any help and ideas.

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1. Re: Late October in Stockbridge - Any Suggestions?

I'ds suggest you try the Shelburne Falls area - just over the hills from Stockbridge - much less crowded, less expensive, yet still 45 minutes to North Adams, Williamstown, Mass MOCA, Clark Art Museum. There is lots to do around historic Deerfield, great restaurants (Gypsy Apple, Tusk N Rattle, Cafe Martin for starters) and B&Bs (try Kenburn Orchards B&B for availability) many local crafts people and artists, great scenery (foliage will be past peak) Worth a look!

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2. Re: Late October in Stockbridge - Any Suggestions?

What do you enjoy doing? Cultural activities or adventure/active type activities?

You will be arriving on the tail end of foliage season, but personally, I enjoy a walk through the woods with dry leaves on the ground too!

There is a water fall at Bash Bish Falls in Mount Washington, Mass. That is in the south west corner of Massachusetts. Monument Mountain in Great Barrington is supposed to be a nice hiking spot in Great Barrington. Jiminy Peak ski area in Hancock has an alpine slide and "mountain coaster". I believe these are only open if it is good weather. You may want to check on that. Also in the area is the Ashuwilltucook "rail trail". This is a paved, 8 foot wide bike/hike/roller blade/ jogging trail that runs from the southern entrance to the Berkshire Mall in Lanesboro on route 8, 11 miles north into Adams. You could rent bicycles, or walk that. Another water fall that I recently visited is Sanderson Falls, at Sanderson Falls Brook state park in Chester. That is about a 1 mile hike from the parking lot.


Hancock Shaker Village in Hancock, on the Pittsfield town line is a "living museum" which you may enjoy.

Chesterwood, a museum where sculptor Daniel French (I hope I got the name right) did some work. He designed the Lincoln Memorial in Washington DC. That museum is in Stockbridge.

Sterling Clark art Museum in in Williamstown.

Mass MOCA (Massachusetts Museum of Contemporary Art) is in North Adams Massachusetts.

The Red Lion Inn is on Main Street in Stockbridge. It is an old historic inn with lots of character. You may want to go have a drink there and stop into the Lion's Den.

Check out a couple of theathers in Pittsfield to see if there is anything you would like to see. The Colonial Theatre on South Street is a beautifully restored 100+ year old theater. Find their web site at www.thecolonialtheatre.org Another theather is the Barrington Stage Company in Pittsfield. www.barringtonstageco.org

There are a number of golf courses in the area you may enjoy, or you could rent a canoe or kayak and go out on one of the local lakes.

I hope something above helps!


Annapolis, Maryland
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3. Re: Late October in Stockbridge - Any Suggestions?

We are traveling to Stockbridge late Oct 08 and wondered what your experience was like and whether you can recommend a good B&B or inn and restaurants? Anything in particular we should do or skip? Thanks!

Dublin, Ireland
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4. Re: Late October in Stockbridge - Any Suggestions?


We had a great time in the whole Berkshires area. In the end, we stayed in an inn in Lee, not too far away from Stockbridge. It ws called the Chambery Inn (hope I spelled that correctly!) and it was really nice - huge rooms, comfy beds and breakfast delivered in a basket each morning. The only thing that wasn't great about it was the absence of people to speak to - it was almost like they would run and hide when you walked-in!

Round and about the area, just driving and experiencing the countryside was great, but a definite must-see is the Norman Rockwell Museum. As a pair of Irish visitors, we got a great kick out of the place, so I'm sure as Americans, it must be a completely different experience - don't miss it.

There are so many small towns dotted around that you can just go from place to place and take it at a slow pace.

It's all good!

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5. Re: Late October in Stockbridge - Any Suggestions?

In Williamstown Mass the Clark Sterling Museum is a little gem that we love. Williamstown is a college town and is near to the Hancock Shaker Village.

6. Re: Late October in Stockbridge - Any Suggestions?

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