A 3-Day Guide to the Berkshires, From Someone Who Called It Home

Historic main streets, farm-to-table cuisine, and outdoor splendor are what define the Berkshires of western Massachusetts. I lived here for nearly two decades, and whenever I go back, these are the places I return to — the ones that feel like home and remind me why this corner of New England draws visitors year after year.

Day 1: Stockbridge and Surrounds

I always like to start in Stockbridge, with a walk down Norman Rockwell’s Main Street. Rockwell spent the latter half of his life here, and the town still carries his imprint. The red-and-white firehouse that shows up in The New American LaFrance is Here! looks almost unchanged today.

For lunch, I’ll stop at Theresa’s Stockbridge Café — the original location of Alice’s Restaurant, immortalized by Arlo Guthrie — or linger in the courtyard of The Red Lion Inn. On summer afternoons, the Inn’s famous porch is still one of the best seats in town.

If I’m visiting between June and October, I make time for Naumkeag. The Gilded Age estate and gardens, designed by Fletcher Steele over 30 years, are a lesson in grandeur and whimsy. On a hot afternoon, I’ll head indoors instead: the Norman Rockwell Museum is a short drive down the road, and it never fails to surprise me with the breadth of its rotating exhibitions. Around the holidays, Stockbridge recreates Rockwell’s Main Street at Christmas — and it really does feel like stepping into the painting.

Day 2: Lenox and Tanglewood

Heading north, I always pull over at Olivia’s Overlook. It’s a trailhead for six miles of hiking, but even if I’m not up for a walk, I’ll bring a picnic and take in the view over the Stockbridge Bowl.

Lenox is a small town with outsized charm. I’ll wander downtown, browse the shops, and if I’m there in theater season, I never pass up Shakespeare & Company. Dinner at Cello is a must. Chef-driven and seasonal, it keeps the spirit of inventive Berkshire dining alive, with menus that shift with the farms and fields around it.

If it’s summer, the evening belongs to Tanglewood. Whether it’s a Boston Symphony Orchestra performance or a John Williams night under the stars, I still get goosebumps every time. Afterwards, I’ll duck into Brava wine bar for Spanish tapas and a glass of something interesting before calling it a night.

Day 3: North County Adventures

On my last day, I like to head north to Mount Greylock. At 3,491 feet, it’s the highest peak in Massachusetts, and the views are staggering — five states on a clear day. I’ve hiked it, I’ve driven it, and both are worth it. Lunch at Bascom Lodge, nine miles from the summit, is a ritual: the WPA-era building itself is a beauty, and the kitchen takes pride in local sourcing. In October, there’s no better place to take in the foliage.

In the afternoon, I’ll trade mountaintops for art. MASS MoCA in North Adams is one of my favorite museums anywhere, set inside a sprawling 19th-century factory complex. I still get lost wandering through Sol LeWitt’s wall drawings — a retrospective so vast it will be up until 2043. The museum’s app makes it easy to navigate, but half the fun is stumbling upon unexpected installations.

Before heading out, I’ll grab brisket at A-OK Berkshire Barbecue and a beer across the way at Bright Ideas Brewery — the perfect send-off before the drive home.

Essentials

• When to go: The Berkshires shine in every season: arts and hiking in summer, foliage in fall, skiing in winter.
• Getting around: Towns are walkable once you’re there, but a car makes exploring easier. Rideshares exist, but not at city scale. Biking is also a beautiful way to see the region.
• Currency & language: U.S. dollar, English.