redlioninnAbout eight years ago, when my husband and I were first dating, we took a trip to Stockbridge, Massachusetts. I can’t recall where we stayed or much of what we did, other than visiting to the Normal Rockwell Museum.

But what I did remember is how absolutely quaint and beautiful the town is, so quintessential New England. Happily, as we discovered during a recent visit with our two kids, it’s hardly changed. We stayed at The Red Lion Inn, a historical 108-room hotel that’s been operating since the late 18th century (rates start at $130 a night, depending on the time of year).

We got a suite, with a separate area that had a pull-out couch for the kids…who ended up crashing with us, anyway. We all adored the clawfoot tub (“FEET!” said my seven-year-old, Max, pointing to the tub’s base), as well as the walk-in shower with dual showerheads. Max enjoyed the room so much he insisted on room service for breakfast.


The hotel’s retained its historical feel—you feel as if you are staying in a beloved grandmother’s enormous home, a grandmother with excellent taste. Lounging is encouraged: There’s a porch with rocking chairs, a parlor with comfy couches and a charming Main Dining Room, where my daughter and I ate breakfast. It has a special sustainable menu featuring local delicacies; the granola was heavenly. 

There’s history everywhere, with antiques and vintage photos lining the hallways (although there are computer areas with Wi-Fi for guests who can’t resist the siren call of modern-day technology). Our kids were fascinated by the beautiful brass elevator, operated by a hotel staffer who kindly took us up and down a handful of times, pointing out the majestic elevator weights that flew by. 

We were in town for two days. We arrived in the afternoon and wandered around the village, window shopping and grabbingcoffee and scones at Daily Bread Bakery. That night, we headed over to the Dakota Steakhouse in Pittsfield, MA, a family-friendly place that looks like a wooded lodge. I’d originally visited as a teen with my family and it was just as tasty as I remembered—warm honey-wheat bread, delicious seafood and steaks, and a great salad bar. The kids got a kick out of the lobster tank, and the waiter manning it gladly introduced them to “Bob” and several other creepy crawlers.

normanrockwellmuseumThe next day, we hit the Normal Rockwell Museum (adults, $15.00 each; anyone under 18, free). Founded in 1969, it houses the world’s largest collection of the artist’s work. My kids are seven and five, and I wasn’t sure they’d have the patience for it, but they enjoyed looking at the numerous paintings involving children, dogs and doctors. Max even noticed The Red Lion Inn pictured in Christmas at Main Street (there it is, in the far right of the painting). The bucolic property also houses Rockwell’s studio, moved over from its location in town, down to the empty Coke bottle on his table.

berkshirebotanicalgarden2Later that day, we spent a couple of hours roaming around the lush and serene Berkshire Botanical Garden (well, it was serene until my kids arrived). My little girl, Sabrina, loved the Hogworts Garden, with its magical bench formed entirely out of branches. The garden was filled with herbs used in past times as elixirs, potions and cures for ailments. berkshirebotanicalgarden4The flowers are magnificent, and there’s a wide expanse of lush lawn where my husband decided to take an afternoon nap, lucky guy. 

The area has several good galleries, antique and crafts shop, but with the kids, we opted out. If we’d had more time we would have also visited Lenox to see The Mount, Edith Wharton’s Estate and Gardens; taken a ride on the Berkshire Scenic Railway Museum; and done a classical music concert at Tanglewood. There’s definitely enough to see and do in the area for several days—but be sure to carve out time for sitting on a porch. 

Ellen blogs daily at Love That Max.