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Wines on the Wing

Perks in the Berks for Families

by Carley Wade

Jul 28, 2018

© The Red Lion Inn

Destinations / North America

When’s the last time you had crispy, local bacon slabs, grilled onions and creamy blue cheese all atop griddled ciabatta bread? Didn’t think so … but sounds pretty good, right?

The recent inventive special that will have you asking yourself why no one’s ever thought of that as an open-faced sandwich is part of the new menu from executive chef Max Kiperman at the Red Lion Inn in the heart of the Berkshires. About halfway between Boston and New York City, foodie epicenters in their own right, (Kiperman comes with a pedigree straight from the former’s Back Bay neighborhood) dairy and vegetable farms abound here in this bucolic enclave — making for lots of scenic pastures and tasty plates.

Dining at the Red Lion Inn © The Red Lion Inn

Dining at the Red Lion Inn © The Red Lion Inn

Red Lion’s menu uses locally raised Berkshire pork loin; ingredients from High Lawn Dairy in adjacent Lee; bread baskets abound with Berkshire Mountain Bakery loaves; and desserts are served with Great Barrington’s SoCo Ice Cream a la mode at the resort’s four dining options. Rather than just the most “formal” main dining room, there’s the Lion’s Den pub with live music; an outdoor Courtyard; and Widow Bingham’s Tavern. From the mix of millennials, Boomers and just-turned-21s in each, it’s pretty clear this isn’t your Grandma’s B&B anymore (although you can still order mainstays like roasted turkey and prime rib year-round).

The revamp holds true in other parts of the property, where the Maple Glen guesthouse kicks it up a notch from the main guesthouse’s Colonial air; an artful mix of antiques and a modern color palette with large spa bathrooms in each is comfortable while striking the right combination of contemporary. A common area features couches and a library, and it’s not uncommon to see local theater groups rehearsing here despite not being guests.

“We are Stockbridge,” says the concierge checking you in, who points out the Red Lion complex in the center of town, where resident Norman Rockwell once painted Main Street scapes that have since become part of the American Everytown, U.S.A. psyche. If you want to grab a stool where he once did, trot down the street to Main Street Café or, for a bit more elevated fare, the Lenox Patisserie calls. Savory soups and Parisian pastries (including delectable gluten-free chocolate cakes) beckon or, in nearby Beckett, check out Jacob’s Pillow for free dance performances in the summertime. Art-lovers can check out Rockwell’s home, now a museum, or writer Edith Wharton’s home, The Mount. Shakespeare & Co. present the best of the Bard a few times a year or classical music fans can take a more relaxed approach with lawn concerts, courtesy of the Boston Symphony Orchestra summer residence at Tanglewood, an outdoor amphitheater just right for the wine-and-cheese picnic set.

Red Lion Inn © The Red Lion Inn

Red Lion Inn © The Red Lion Inn

Nearby, Great Barrington is where it’s at for a bit of younger fun and, while its blue-collar soul feels a bit more gentrified to a public-works project that removed many of the shade-bearing trees downtown, there’s still plenty of earthy-crunchy vibe to spare (not unlike the locally made granola at Fuel coffeehouse’s new location). Two toy stores, plenty of clothing shops featuring local designers and high-end labels at expanded boutiques like Louisa Ellis, along with a slew of fun restaurants, like The Well pub and Prairie Whale (don’t miss fried chicken at brunch or cornhole while you wait), make for some fun afternoons of strolling and noshing.

In for more activity? Try hiking Monument Mountain for stunning views of Housatonic River Valley or head on over to Bash Bish Falls for an easier walk to Massachusetts’ highest waterfall. It’s just a short walk to Taconic State Park in New York and, despite these two states’ famed baseball rivalries, all’s copacetic at this border beauty.


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