Imagine if you could be whisked away to the Berkshires. What would you do? Well, this is what we’d do. Although we call this “an ideal day,” doing everything in this narrative would require more than a day, and maybe even have to be done during different seasons for the best experience. Read on and envision yourself at each stop.

We’ll start in the Northwest corner of the county in Williamstown, home of Williams College, where we will take in a performance at the Williamstown Theatre Festival. From there we’ll check out the latest exhibition at The Sterling and Francine Clark Art Institute.

Since we’re looking at art, the galleries at Mass MoCA – The Massachusetts Museum of Contemporary Art – in North Adams will be our next stop. A drive to the summit of Mt. Greylock will follow, where we’ll pick up the Appalachian Trail and hike south into Cheshire.

At the Trail’s intersection with the Ashuwilticook Rail Trail we’ll hop on our bicycles and pedal south along the shore of Cheshire Reservoir (interested in lakefront property? contact us). In Pittsfield we’ll swim, fish and boat on Onota and Pontoosuc Lakes and follow that up with a tour of Arrowhead, the home of Herman Melville, author of Moby Dick.

Next we have tickets to the latest offerings at both Barrington Stage Company and the Colonial Theater. While still in Pittsfield we’ll see exhibitions and engage in the activities at the Berkshire Museum. Since there’s good snow cover, before we leave Pittsfield we’ll try our hand at downhill skiing and snowboarding at Bousquet Mountain.

The skis are still on the roof of the car and there’s still snow so the slopes at Jiminy Peak Mountain Resort in Hancock are the next stop. We’ll see baby animals, participate in a workshop and go to a country fair at the Hancock Shaker Village before moving onto Lenox and visiting Edith Wharton’s The Mount, an historical reminder of the continuing pull of the Berkshires to those involved in the arts. For a more contemporary example of that pull, we’ll have a picnic on the great lawn at Tanglewood while listening to the Boston Symphony Orchestra.

Moving on, the Berkshire’s pull on old art and new artists will be on display at the Shakespeare & Company performance we’re going to next, maybe we’ll get lucky and see A Midsummer’s Night Dream before we go to Stockbridge. The first stop in Stockbridge will be the Berkshire Botanical Gardens because we like gardens. We’ll fit the Norman Rockwell Museum between our tours of the Gilded Age residences, Naumkeag & Chesterwood and finish Stockbridge by attending a performance at the Berkshire Theater Festival.

It’s almost time for lunch and we’re in Great Barrington where there are over fifty restaurants for us to choose from. Something interesting is always going on at the Mahaiwe Performing Arts Center and we’re going to go. On the way out of town, since there’s snow again, we’ll take the skis off the car and test the slopes at Ski Butternut. In Monterey we have appointments with a Realtor to see lakefront property on Lakes Buel, Garfield and Stephens (interested? call us 413-250-6149). There are a lot of lakes and a lot of lakefront property in Otis where we’ll water ski on Otis Reservoir, kayak on Big Pond and ice fish on Benton Pond. In Becket, continuing our lake viewings, we’ll see what Center and Yokum Ponds have to offer. No trip to Becket would be complete without taking in a performance at Jacobs Pillow Dance Festival – I’ve never understood how they do the things they do – followed by dinner at the Dream Away Lodge.

A long dirt road through State Forest will get us to Tyringham where we’ll hike the Tyringham Cobble, pick up the Appalachian Trail and follow it to Goose Pond and the town of Lee. It’s the end of our imaginary day and we’re going to finish it with some shopping at the Lee Premium Outlets. The entrance ramp to the Massachusetts Turnpike is here and maybe it will take us home. We’ve seen a lot but we’ve missed even more – there is still much left to do and see on the next trip to the Berkshires.