By Lauren Matison Photographs by Tony Cenicola

Lauren Matison, a regular contributor to New York Times Travel, lives in the foothills of the Berkshire Mountains and has been writing about the region for more than 10 years.

Start your Berkshires weekend in the town of Great Barrington, in the region’s south. Railroad Street, named for a 19th-century former depot, is a charming microcosm of the Berkshires’ renaissance. Pick up a maple latte ($5.25) at Marjoram + Roux, then peruse Railroad St. Collective, which spotlights works by regional artisans, including Cheryl Pagano’s plant-based textiles and Aaron Meshon’s whimsical illustrations. Pop into Bon Dimanche, a new boutique with screen-printed apparel and affordable décor (fellow small businesses raised funds to save the store after it fell victim to a cyberscam this year). In the alley, don’t miss two giant murals honoring the N.A.A.C.P. co-founder and Great Barrington native W.E.B. Du Bois, painted by the Railroad Street Youth Project.

Beyond Great Barrington’s trendy shops and rainbow crosswalks are remnants of a rich and complex history. Follow a free self-guided audio tour that begins at the Mason Library, which features a free exhibit on local civil rights activists. Crisscrossing downtown, the full tour may take around an hour. One notable stop is the Clinton A.M.E. Zion Church, where Du Bois attended services; it is set to be restored as the Du Bois Freedom Center by 2027.

When Julie and Stephen Browning opened No Comply Foods, their brick-and-mortar restaurant, in April, there was a collective cheer in town: no more waiting until the Saturday pop-up at the Great Barrington Farmers Market for a golden milk latte ($6) or loaded Japanese sweet potato drizzled with olive oil, tahini and house-made chile crisp ($14). The light-filled space with funky art, flower-topped tables and corner booths offers a daily changing menu (the sweet potato is a constant) that champions local farms and inventive, veggie-heavy food. (Stephen was formerly the executive chef at the nearby farm-to-table institution Prairie Whale.) The restaurant is counter-service only, a leaner business model that its owners say allows them to pay its smaller staff better wages. (There is also a no-tipping policy.)

Music lovers have been flocking to the Berkshires for decades to hear the greats, including Louis Armstrong, Janis Joplin, Bob Marley and James Taylor (who just celebrated 50 years of performing at Tanglewood). The Barn, a short drive from Great Barrington in the town of South Egremont, keeps the beat going year-round in a space with a wabi-sabi feel and a big, glowing peace sign. The co-owner Jenny Rubin programs acts that pack a full house, be it a Grateful Dead cover band, a New Orleans-style blues outfit or the celebrated local jazz singer Wanda Houston (tickets around $20). Take your post-concert high a few minutes down the road to the newly opened Hys Fried for fried chicken and a biscuit ($14) and dancing to vinyl records on the red-and-black checkerboard floor.

The Mount, the summertime retreat of the Pulitzer Prize-winning author Edith Wharton, sits on a 50-acre public park.

At No. Six Depot, a cafe in an 1834 train station in the town of West Stockbridge, sip a cappuccino ($4.50) on the porch overlooking Lenox Mountain and the peaceful flow of cyclists and plein air artists. Up the street is the 16-acre TurnPark Art Space (adult entry $14, free under 12), a former marble quarry turned lush art park. Meander on and off the trails, spying contemporary pieces amid a vast grassy field — like the Austria-based Vadim Kosmatschof’s towering mirror sculpture, reflecting the autumnal blaze. West Stockbridge’s crown jewel is Shaker Mill Books, which had to expand into the historic gristmill next door to house its eclectic collection of more than 30,000 used, out-of-print, new and rare books, many offered at a bargain price.

In 1902, Edith Wharton, the first woman to receive a Pulitzer Prize, moved into the Mount, a 17,000-square-foot neo-Classical mansion that she designed and had built against a rocky knoll in the town of Lenox. On a one-hour guided tour (included in entry; $20 for adults, under 18 free), learn about her writing habits (in bed) and how she defied Gilded Age expectations of women, traveled abroad annually and published 40 books in the 40 years between 1897 and 1937, including “The Age of Innocence” and “The House of Mirth.” Until Oct. 20, the Sculpture at the Mount exhibition showcases 27 art pieces throughout the gardens and hiking trails, and you can have your spine tingled year-round with evening ghost tours ($30) that Wharton, who feared phantoms yet wrote about them, would most likely skip.

In a region bubbling over with talented pizzaiolos, one of the hottest pizza scenes is in Lenox. Molly Lyon-Joseph opened Pizzeria Boema, a wood-fired Neapolitan-style pizza joint in the midst of the pandemic — and while running its sister restaurant Frankie’s next door. Take a seat in the cozy art-filled space or century-old barn to try the popular buffalo-mozzarella margherita ($21) or one of many vegan options: One comes with wild mushrooms, arugula and plant-based mozzarella on a thin cauliflower crust ($20). Fall pies include the Bianca ($20) with butternut squash, Gorgonzola, walnuts and kale, and the Bresaola ($22) with dried figs and stracciatella. After lunch, check out the backyard cornhole (you can always come back for s’mores by the fire pit in the evenings).

In Lenox, all roads lead to Kennedy Park. Just north of the town center, the 500-acre hardwood forest has vernal pools (temporary ponds that are vital wildlife habitats), colorful canopies of oak, ash and beech trees, and more than 15 well-groomed miles of hiking and biking trails — including old carriage paths traveled by Theodore Roosevelt and Franklin D. Roosevelt while staying at the prominent Aspinwall Hotel (which burned down in 1931). Get a free trail map at Arcadian Shop on the eastern edge. Then, for a relaxing under-three-miles-round-trip jaunt, follow the Woolsey Trail to the lookout gazebo, with views of Mount Greylock. From there, take the Coakley Trail south to the Kennedy Park Belvedere overlook, via the Picnic side trail, to admire the mountain vistas and Housatonic River Valley.

Hot Plate Brewing Co. an inclusive and community-driven seven-barrel brewhouse and taproom that opened in 2023, is hopping with people gathered for live music and great beer (from $3 for five ounces, $7 for a pint). Try the Capable of Anything, a chamomile blonde ale, or the Kardia, a habanero chocolate stout inspired by the co-owner Sarah Real’s Mexican heritage. This fall and winter, proceeds from sales of Kardia will be donated to the Pittsfield Area Council of Congregations, to help provide heat for low-income households.

A ski jump’s distance from Jiminy Peak Mountain Resort in the town of Hancock, Bluebird & Co. is the latest restaurant from Nancy Thomas and Bo Peabody (of the wildly popular Mezze Bistro & Bar in nearby Williamstown). Opened in July 2023 with a local, seasonal ethos, the restaurant leans in to an après-ski vibe with cozy booths, wood-paneled walls, vintage black-and-white portraits of people from the Berkshires, a bar area with sports playing quietly on the two TVs and a groovy playlist peppered with the likes of Brenton Wood and Creedence Clearwater Revival. Bluebird’s regulars come back for the double-patty Okie burger with fried onions ($17) and the braised chickpeas with green harissa, labneh, mint and parsley ($12).

Along the Mohawk Trail — one of the country’s first scenic byways, originally used by Native Americans as a trade and travel route — is the Tourists hotel, remodeled from the 1960s Redwood Motel. Its wood-beamed lounge looks as if it was designed for autumn getaways and midcentury-modern enthusiasts. Post up next to staycationing locals and order a Sumac Spritz ($15), made with blanc vermouth, prosecco and sumac, picked from the property’s 80-acre forest. Ask for one of a dozen board games at the bar, then sink into a leather couch by the fire. If the Sing for Your Slumber live-music series has the night off, you can count on a soundtrack of 1960s country-blues and psychedelic folk troubadours. The only reason to move will be for s’mores ($7 per kit) around the fire pit outside.

The Hoosic River and the Ashuwillticook Rail Trail in Adams.

In the town of North Adams, explore Greylock Works, a 240,000-square-foot former cotton mill, now home to shops, artists’ studios, a distillery, a cafe and, more recently, loft condos. Before they sell out, order a pistachio sweet roll or a feta-and-hot-honey croissant (around $6 each) at the newly opened State Food + Drink. Then shop for potted plants, abstract paintings and Vietnamese condiments at the 328North Studio (owned by State’s chef Tu Le), before heading next door to Your Neighbor Studio, a used-clothing and furniture shop. Its owners live part time in Brooklyn, so the space runs on an honor system when it’s unstaffed, although fellow shopkeepers look in (simply Venmo them for the Picasso print or Issey Miyake leather jacket you might find there). Douglas Gilbert, another New York transplant, offers drawing classes in his studio, which is lined with his crosshatch artwork.

Like Herman Melville, who wrote “Moby-Dick” in the whale-shaped shadow of Mount Greylock, countless others have discovered the region’s wellspring of creativity by taking a hike. Just outside downtown North Adams, the Cascades Trail (one of around 250 hiking trails in the Berkshires, according to the new outdoor resource BerkshiresOutside.org) is a roughly two-mile out-and-back trip that would have vanished if not for a community petition in 1938 that saved the area from deforestation. Infused with the scent of pine and wet rocks, the path meanders along Notch Brook and up verdant woods tinged with gold leaves. Stepping over roots and muddy patches, you’ll climb a short bend and suddenly see a deep gorge and a 45-foot waterfall. Even on a spectacular fall day, you will most likely have the glen all to yourself.

How do you represent 25 years of a museum’s journey? MASS MoCA, which opened in a complex of abandoned mill buildings in downtown North Adams in 1999, has grown into one of North America’s largest contemporary art museums. The anniversary exhibition “MASS M0CA by the NUMB3R5” (through May 2025) presents a dazzling display of data, including 8,640 gallons of paint used in exhibitions, the 5,750 pencils Sol LeWitt used for 105 large-scale drawings, and 2.5 million attendance stickers issued. Also don’t miss Gunnar Schonbeck’s interactive “No Experience Required” music room; Amy Podmore’s blinking “Audience,” in which motorized eyeballs hold your gaze; Louise Bourgeois’s “Untitled” marble sculpture, a U.S. debut; and a James Turrell retrospective that includes a 40-by-40-foot freestanding Skyspace, the largest of the artist’s series of immersive light chambers around the world, built beside the Hoosic River.