Joshua James, owner of San Francisco’s Ocean Beach Café and a former bartender and beer brewer, sees that shift reflected across age groups. “The big surprise was the industry didn’t get their guaranteed 21-year-old customer in this era,” he tells Observer, referring to the assumption that once someone reaches the legal drinking age, they become a reliable consumer. Instead, drinking patterns now diverge more sharply by generation, with younger adults opting out earlier and older groups reassessing habits shaped over decades, per James.

Alongside spirit-free cocktails built in familiar formats to traditional boozy drinks, many zero-proof bars now offer drinks made with adaptogens, kava or hemp-derived ingredients like CBD. That approach has helped zero-proof bars take hold as places people actually want to spend time, built around thoughtful drinks and social energy rather than abstinence alone. From San Francisco to New York, these are the zero-proof bars across the country leading that shift.

Sans Bar

• 918 Congress Ave., Austin, TX 78701

Long before “zero-proof” became a well-known category, Sans Bar was already operating as a dedicated non-alcoholic bar in downtown Austin. Founded in 2017, it’s widely regarded as one of the first of its kind in North America. The bar’s programming—pop-ups, collaborations and rotating menus—has been influential in shaping the broader sober-curious movement, particularly in Texas. Specific menu highlights include a pecan praline old-fashioned, a spirit-free Mezcal Ranch Water and the Ume Moon, featuring non-alcoholic bourbon, caramelized fig syrup, white truffle, lemon and ume spritz.

Ocean Beach Café

• 734 La Playa St, San Francisco, CA 94121

Ocean Beach Café was intentionally framed as a café, not a bar—a decision James says was meant to lower barriers and encourage sampling. “I absolutely called it a cafe to create the maximum amount of impact through awareness, free samples and social cocktails that are beautiful, functional and for adults,” he tells Observer. In addition to casual daytime fare like sandwiches and salads, the menu prioritizes non-alcoholic spirits and functional ingredients, including Good Buzz Daisy, made with non-alcoholic mezcal, Bonbuz adaptogenic elixir, Dhos Orange, lime and agave.

Gratitude Zero-Proof Beverages & Kava

• 2752 Colorado Ave, Colorado Springs, CO 80904

Colorado Springs’ first entirely non-alcoholic bar takes an apothecary-driven approach to drinking, with house-made syrups and ginger beer forming the backbone of the menu. Herbs, roots and spices are used with intention, resulting in handcrafted mocktails that prioritize flavor as much as function. The lineup includes a carrot-ginger margarita finished with black lava salt, a zero-proof mule built on house ginger beer and fresh mint grown on-site and a sparkling, brut-based option that leans celebratory without feeling (or tasting) overly sweet.

Dry Spokes

• 1901 Leavenworth St, Omaha, NE 68102

Dry Spokes began as a mobile pop-up before opening a brick-and-mortar space just outside downtown Omaha in early 2023. Operated by married duo Leah Wright and Mi-Ya Mata, the veteran-, female-, Indigenous- and LGBTQ-owned bar adapts familiar cocktail formats to non-alcoholic spirits, with drinks like an old-fashioned, Peachy Keen and Italian Smoke paired with lighter, nostalgia-inducing options like Cotton Candy. There’s also a “Surprise Me” offering that lets bartenders build drinks based on guest preferences.

Mockingbird

• 213 7th Ave, Brooklyn, NY 11215

In Park Slope, Mockingbird pairs creative non-alcoholic cocktails with what it bills as New York City’s largest selection of NA beers and wines. Food plays a supporting role, with light bites like garlic-parmesan popcorn and truffle pretzel bites, plus weekend brunch and daytime café service using beans from local micro- and nano-roasters. One of the bar’s signature drinks, The Litmus Theory, uses butterfly pea flower, Sobreo Black Cardamom and sparkling non-alcoholic wine; its color shifts from blue to purple when acid is added.

Club Seltzer

• 500 Bellevue Way NE floor 2, Bellevue, WA 98004

Inside Lincoln Square South Food Hall, Club Seltzer takes a different tack from cocktail-first zero-proof bars, focusing instead on adaptogen-infused seltzers. The Pacific Northwest’s first seltzer-focused, alcohol-free bar crafts drinks with sparkling water and real fruit, much of which is dehydrated on-site. Offerings include the Ruby Refresher and Banana Havana, with most drinks customizable through add-ins such as matcha, blue spirulina, aloe and probiotics.

Nightshade 

• 32 Banks Ave #105, Asheville, NC 28801

Nightshade is a late-night lounge in Asheville’s South Slope where music, not alcohol, sets the tone. Open since September 2025, the space hosts a rotating line-up of DJs and live sets spanning house, funk, techno and disco. The drink menu moves between zero-proof classics, like a dirty martini and old-fashioned, plus more experimental builds like St. Winter’s Roar, an Irish iced coffee with espresso and non-alcoholic whiskey. Functional drinks are also central to the list, from adaptogenic seltzers like Uplift (a mango-flavored option with CBD, lion’s mane and vitamin B12) to cannabis shots.

No More Cafe

• 352 E 13th St, New York, NY 10003

No More Cafe opened in the East Village in April 2024, serving as both an all-day café and a non-alcoholic cocktail bar. Coffee, tea and matcha flow through the morning, while afternoons and evenings feature a rotating list of house NA cocktails alongside non-alcoholic beer and wine. Drinks, like The Urban Illusion—a dark-cherry-forward cocktail with vermouth-style botanicals and bitters—are made sans extracts, preservatives or artificial flavors, ensuring the highest quality ingredients (and experience). Guests can also add functional elements à la carte, including special blends focused on energy and focus or on calm and relaxation.

Good News Bar

• 3821 Park Blvd, San Diego, CA 92103

Named after Mac Miller’s “Good News,” this San Diego spot offers health- and wellness-centric mocktails and spirit-free drinks modeled on classic formats. Expect to see plenty of adaptogens, herbs, kava and CBD, alongside standard mocktails designed for guests who avoid functional ingredients. Flying Away, a cold-brew-based concoction with cardamom, orange, aromatic bitters and a hemp-based botanical spirit, captures that balance clearly. Here, coffee and pastries give way to evening cocktails, NA beer and de-alcoholized wine.

Whether it’s a fireside fondue table, a heated rooftop chalet or a private furnished igloo, these winter pop-ups are as much about atmosphere as they are about food and drink. Some are meant for lingering, with comfortable seating, limited tables, and multi-course menus ideal for long meals, while others are louder and more social, attracting a see-and-be-seen crowd. Either way, they give people somewhere to go during the dead of winter and give restaurants the flexibility to try ideas that wouldn’t usually make sense the rest of the year. Below, a guide to the New York City winter pop-ups worth seeking out this season.

Winter House at elNico

• 288 N 8th St, Brooklyn, NY 11211
• Williamsburg
• Runs through: February 2026

The rooftop greenhouse atop The Penny Williamsburg, elNico, adapts to winter without sacrificing its original appeal. Through February, the vibrant space stays bright and plant-forward, with greenery and warm lighting in lieu of over-the-top seasonal décor. The kitchen sticks to what it already does well—mole tastings, esquites and tacos—while the cocktail list leans agave-forward with a few cold-weather adjustments. Don’t miss the ElNicocoa, a spiced Mexican hot chocolate finished with cinnamon whip and a churro-style pastry. 

Fireside Fondue at Society Café

• 52 West 13th Street, New York, NY 10011
• Greenwich Village
• Runs through: February 2026

While you may not be able to sit down to fondue or raclette in the Swiss Alps, Society Café’s Fireside Fondue setup comes close enough, sans the plane ticket. Set just off the lobby at Walker Hotel Greenwich Village, the experience revolves around a single table positioned beside a working fireplace. Only a handful of parties are booked each night through February, keeping the scale intentionally small. Diners can indulge in Swiss cheese fondue with toasted sourdough and sausage, followed by chocolate fondue with fruit and housemade sweets. Live jazz plays quietly while hot toddies and hot chocolate circulate.

Rooftop Igloos at Public Hotel

• 215 Chrystie St, New York, NY 10002
• Lower East Side
• Runs through: Winter 2026

Public’s rooftop igloos are geared toward groups rather than seclusion. The structures open toward the skyline and sit close enough to the surrounding bar to maintain a sense of shared energy rather than total privacy. Inside, the igloos are outfitted with candles and faux-fur throws to stay warm while feasting on cold-weather staples, such as cheese and chocolate fondues and spiked hot chocolate. Reservations follow a tiered pricing structure by day and time, and igloos accommodate up to 10 guests, making them best suited to group dinners and planned nights out.

Lindens Winter Village

• 2 Renwick St, New York, NY 10013
• SoHo
• Runs through: March 2026

Lindens Winter Village takes over the courtyard at Arlo SoHo with three fully enclosed, heated yurts running through March. Interiors are kept simple—soft lighting, practical furnishings, and restrained seasonal touches—so the focus remains on comfort rather than kitschy theme. Guests can opt for a structured four-course menu at brunch, lunch or dinner, or take a more flexible route with a tableside cocktail journey featuring Lindens’ winter drinks alongside the full menu to share.

Haven Ski Chalet at Haven Rooftop

• 132 W 47th St, New York, NY 10036
• Times Square
• Runs through: March 2026

Located atop the Sanctuary Hotel, Haven Rooftop fully leans into its ski chalet setup, dressing the space with evergreen garlands, cranberry bundles, flannel pillows and twinkling string lights. Unlike many winter pop-ups that save their energy for late nights, this one is squarely a daytime affair. From late morning through early afternoon, guests book chalet-style brunch tables, with bottomless mimosas or bellinis included alongside an entrée. The restaurant stays intentionally buzzy, offering warmth and seasonal atmosphere as a complement to Times Square’s constant motion—not an escape from it. It’s best suited to brunch plans that benefit from a festive winter backdrop and a little crowd buzz.

Snow Lodge at The William Vale

• 111 N 12th St, Brooklyn, NY 11249
• Williamsburg, Brooklyn
• Runs through: Winter 2026

Westlight at The William Vale trades its open-air rooftop feel for a fully heated winter setup, where snow-capped trees, faux-fur throws and low lighting frame expansive skyline views. The menu leans Alpine-adjacent, with cheese fondue, oversized Bavarian-style pretzels and cold-weather libations like spiked Mexican hot chocolate and clarified coquito. No matter what’s in your glass, the main draw is the setting itself, with the view and swanky vibes carrying as much weight as the menu.

Alpine Luxe: The Ski Chalet Experience at Industry Kitchen

• 70 South St, New York, NY 10005
• Seaport District
• Runs through: February 2026

Industry Kitchen transforms its East River frontage into a full-scale Alpine installation in partnership with Bucket Listers and Veuve Clicquot. The Alpine Luxe Experience includes private igloos and fireside seating, set against ski-lift installations and snow-dusted backdrops overlooking the Brooklyn Bridge. Reservations run in 90-minute blocks and include a three-course menu that opens with a lobster bisque shooter served in a shot ski, followed by hearty mains and tableside-torched s’mores, with a separate kids’ menu available for younger guests.

Snowglobe in the Sky at Ophelia

• 3 Mitchell Pl 26th floor, New York, NY 10017
• Midtown
• Runs through: Winter 2026

Amid the bustle of Midtown, Ophelia brings back Snowglobe in the Sky with hundreds of candles, plush white rugs and winter-themed projections washing across the walls. The atmosphere is busy but contained, anchored by the bar rather than constant movement through the room. Cocktails are the main draw—especially the El Paso Old Fashioned, which blends rum, tequila, banana, cacao and cinnamon—but the food menu holds its own. Guests can nosh on caviar-topped potato bites, charcuterie boards, French onion sliders and elevated pub grub while taking in skyline views.

Chesa at The Peninsula New York

• 700 5th Ave, New York, NY 10019
• Midtown
• Runs through: March 21, 2026

Chesa—named for the Romansh word for “inn”—returns to The Peninsula New York’s West Terrace through March 21, 2026. Modeled after the long-running Swiss restaurant at The Peninsula Hong Kong, the installation features four private, heated chalets arranged around a central firepit. Each wood-clad structure is outfitted with Adirondack-style lounge seating, plush rugs, rustic chandeliers and vintage posters. The menu is grounded in Swiss comfort staples, like raclette as well as cheese and chocolate fondues paired with a focused list of Swiss wines, with optional add-ons like cognac and caviar tastings for those looking to elevate the experience.

The Pool House Winter Retreat at The Rockaway Hotel

• 108-10 Rockaway Beach Dr, Rockaway Park, NY 11694
• Rockaway Beach, Queens
• Runs through: April 2026

At The Rockaway Hotel, the Pool House shifts from summer gathering spot into a cold-weather retreat. The indoor pool and adjacent lounge remain open through the season, offering an unusual city combination of heat, water and ocean air. Fireplaces, subdued lighting and comfortable seating set a slower pace, while the bar leans into winter-appropriate drinks like hot toddies made with bourbon, tequila or spiced rum, along with thoughtful non-alcoholic options like pear and rosemary sparkling lemonade and a fizzy pineapple-ginger concoction. For something more satiating, the all-day menu features sandwiches, salads and bowls. Hotel guests and day-pass holders can also access cedar barrel saunas and the heated pool, making this less of a themed pop-up and more of a seasonal reset—especially appealing for New Yorkers willing to head toward the shoreline when the crowds thin out.

Igloos at Somewhere Nowhere

• 112 W 25th St Floor 38 & 39, New York, NY 10001
• Chelsea
• Runs through: March 14, 2026

Somewhere Nowhere’s igloos offer a private alternative to rooftop winter dining. Fully enclosed and insulated, the teardrop-shaped igloos seat up to five guests. Each two-hour reservation includes a bottle of Champagne, with additional food and drinks available for order on-site (don’t miss the grilled cheese and tomato soup, or the hot honey arancini). Scheduled separately from late-night programming, this experience is more about seclusion and skyline views than high-energy camaraderie, encouraging guests to slow down and stay for a while.

Magic Hour Mountain Lodge

• 485 7th Ave 18th floor, New York, NY 10018
• Midtown
• Runs through: March 2026

Magic Hour Rooftop at Moxy Times Square embraces winter with Magic Hour Mountain Lodge, a chalet-style takeover of its west terrace running through March. Timed to coincide with the Winter Olympics, the installation is lively, with DJ sets and watch parties. Lodge-inspired décor, snowy accents and leather lounge seating draped with faux-sheepskin throws give the space a distinct après-ski vibe. In terms of food and drink, the bar favors seasonal cocktails, like a vodka-spiked white hot chocolate and a winter spritz with white cranberry and prosecco, while the menu supports both brunch and nights out, with indulgent standouts including crème brûlée French toast, Dubai chocolate croissants and cotton candy pancakes. 

Many of the year’s most notable launches carry fewer than 1,000 guests—and some fewer than 150—yet devote more space to suites and public rooms than earlier generations of ships. Accommodations are trending larger, often starting around 300 to 400 square feet and, at the top end, expanding to more than 1,000 square feet. Floor-to-ceiling windows, private terraces and layouts designed around natural light are becoming the standard, with public spaces that feel understated rather than flashy. Dining is also evolving, with more open kitchens, chef collaborations and dedicated culinary programs.

Major hospitality brands such as Four Seasons and Ritz-Carlton are entering the category, while established lines are refining their own aesthetics through more residential interiors and destination-driven itineraries. Even the expedition sector is adding smaller ships that prioritize comfort and contemporary design over the equipment-first approach that once defined the space. The luxury ships debuting in 2026 underscore this evolution with sleek superyachts, all-suite layouts, Michelin-caliber dining and a level of polish more often found on land than at sea—until now. 

Four Seasons I

• Debuting: March 2026
• Sailing to: Mediterranean and Caribbean

Four Seasons makes its entry into yachting in March 2026 with Four Seasons I, a 95-suite vessel built to feel more like a private yacht than a conventional cruise ship. The smallest suites start at 473 square feet—large by industry standards—and all come with floor-to-ceiling windows and private terraces. The standout is the nearly 10,000-square-foot Funnel Suite, wrapped in a single, curved glass façade that delivers panoramic views. Retractable walls, open-air lounges and a full-beam marina underline the brand’s emphasis on space and proximity to the water. Dining spans eleven venues overseen by executive chef Armando Ferman Toledo, including a new Chef-in-Residence program that brings Michelin-recognized Four Seasons chefs on board select sailings.

Emerald Kaia

• Debuting: April 2026
• Sailing to: Mediterranean, Red Sea, Seychelles & the Indian Ocean

Emerald Cruises expands its small-yacht footprint in April with its 128-guest Emerald Kaia. Unlike many ships in this passenger range, Kaia’s accommodations offer real breathing room. Balcony Suites start at 340 square feet, while the Terrace and Yacht Suites stretch to 830 and 879 square feet, each with private outdoor space that functions as a second living area. For guests craving even more square footage, the 1,407-square-foot Owner’s Suites add a private spa pool on the terrace.

Around the ship, the design emphasis is on indoor-outdoor living. The bow lounge has sunbeds and a spa pool, the gym opens directly to fresh air, and the marina platform sits at water level for swimming or using the yacht’s water toys. Dining remains intimate, too, with La Cucina & Terrace and the eight-seat Night Market Grill, giving the ship a more boutique hotel feel.

Viking Mira

• Debuting: June 2026
• Sailing to: Mediterranean, Scandinavia, British Isles

Viking Mira joins the line’s adults-only ocean fleet in June, carrying 998 guests in an all-veranda layout identical to its sister ships. Every stateroom features a private balcony, heated bathroom floors, a king-size bed and the sleek Scandinavian interiors for which Viking is known. Accommodations range from 288-square-foot Veranda Staterooms to the 1,488-square-foot Owner’s Suite, which adds a dining room, boardroom and private sauna.

One of the ship’s strongest features is the Nordic Spa, complete with a snow grotto, cold plunge, steam room and Finnish sauna. Public spaces follow the same minimalist aesthetic, from the library-like Living Room lined with bookshelves to the two-deck, forward-facing Explorer’s Lounge wrapped in glass for panoramic views.

Dining is a highlight, with venues that loyal Viking guests routinely call out—especially Manfredi’s, the fleet’s consistently top-rated Italian restaurant—alongside The Chef’s Table and other rotating, regionally inspired options.

Orient Express Corinthian

• Debuting: June 2026
• Sailing to: Mediterranean, Caribbean

Orient Express brings its century-old rail glamour and French design heritage to the water with Orient Express Corinthian, the brand’s first sailing yacht, debuting in 2026. Designed for just 108 guests, the ship has a residential feel: even the smallest suites exceed 450 square feet, while upgraded categories add marble baths, private jacuzzis and—at the very top—striking two-story layouts with separate lounges. Rather than replicating vintage Art Deco, the design borrows its clean lines and pairs them with warm woods and open, light-filled rooms.

Dining is a central part of the onboard experience. La Table de l’Orient-Express by Yannick Alléno showcases menus developed with the Michelin-starred chef, served beneath sculptural glasswork. Pavillon d’Or offers a more relaxed French-Mediterranean mix, while Bar de la Plume provides a quiet setting for cocktails. Shared spaces include an infinity-edge pool, spa, and understated lounges—positioning Corinthian not as a traditional cruise ship, but as a small-scale, design-forward entry into luxury sailing.

Magellan Discoverer

• Debuting: September 2026
• Sailing to: Antarctica

Magellan Discoverer is Antarctica21’s newest small expedition ship—built for travelers who want a real Antarctic adventure with a higher level of comfort than most vessels in the region. Designed for just 76 guests on fly-and-cruise trips (and up to 96 on sea voyages), it maintains an intimate experience while incorporating meaningful upgrades. For example, every cabin features a private balcony, a seating area and a modern bathroom—attributes not typically found on many polar vessels. The layout favors easy movement, from smooth boarding for Zodiac excursions to well-planned observation decks for wildlife and ice watching.

Rather than leaning heavily into rugged expedition styling, Magellan Discoverer takes a quieter, more polished approach. It’s still purpose-built for Antarctica, but with warmer interiors and thoughtful creature comforts that set it apart from the more utilitarian ships that typically operate this far south.

Seven Seas Prestige

• Debuting: December 2026
• Sailing to: Caribbean, Mediterranean

Seven Seas Prestige, Regent Seven Seas Cruises‘ first new ship in more than a decade, arrives in December 2026 with a suite-only layout that expands on the line’s already generous approach to space.

The yet-to-launch 822-guest vessel is 40 percent larger than earlier Regent ships, but it carries only 10 percent more passengers, resulting in unusually generous space throughout. All 12 accommodation categories are suites with private verandas. At the top is the new Skyview Regent Suite, an 8,794-square-foot, two-level residence positioned above the bridge. It includes two bedrooms, 2.5 bathrooms, a private gym and sauna, a glass-walled dining area, a library-style lounge, and a 3,703-square-foot wraparound balcony. A floating natural-stone staircase and private in-suite elevator connect both floors. Guests also receive a personal butler, daily spa treatments, and a private car and guide in every port of call.

Elsewhere on board, the ship adds new dining concepts—11 restaurants and bars total, including Azure, a Mediterranean mezze venue—plus updated lounges and the line’s signature Serene Spa & Wellness program.

Star Explorer

• Debuting: December 2026
• Sailing to: Mediterranean, Scandinavia, United Kingdom

When it launches in December 2026, Star Explorer will become Windstar’s newest all-suite yacht—and one of its most agile. The 224-guest ship carries just 112 suites, including two Horizon Owner’s Suites with wraparound balconies and a mix of full-veranda and infinity-window layouts.

Its real distinction is where it can actually sail. A small, shallow-draft hull enables the Star Explorer to reach places inaccessible to larger vessels, including river ports such as Bordeaux and Rouen, as well as central London, and hard-to-access harbors like San Sebastián and Saint-Jean-de-Luz. Windstar is also among the few cruise lines that keep ships in Europe year-round, which means itineraries stretching into late winter—sometimes visiting destinations most lines only visit in high season.

Back on board, the atmosphere stays deliberately understated. Familiar spaces return—the Yacht Club Café, the watersports marina and open-air deck lounges—paired with updated dining and, of course, the line’s reliably warm crew.

S.S. Emilie

• Debuting: March 2026
• Sailing to: The Danube

Uniworld adds its first new ship in five years with the debut of the S.S. Emilie. The 154-guest vessel draws its design inspiration from Austrian painter Gustav Klimt and his muse, Emilie Flöge, incorporating Art Nouveau patterns, vibrant greens and blues, and signature gold detailing throughout the public spaces. The Art Nouveau influence is evident throughout the public spaces—not just a few rooms—with a restaurant, lounge and bar explicitly designed for this ship, rather than adapted from earlier vessels.

Cabins follow the line’s boutique-hotel approach, but S.S. Emilie introduces a notable new option: guests can combine a Grand Suite with the adjoining Deluxe French Balcony stateroom to create a genuine two-bedroom suite—something rarely seen on European river vessels of this size. The result is a ship that blends Uniworld’s decorative style with a few thoughtful upgrades for travelers who want more space on the rivers.

The Berkshires is a true year-round vacation destination, but fall just may be its finest hour. Hillsides burn with reds and golds, orchards brim with apples ready for picking, and cultural programming is in full swing. Festivals and community events, from the Lenox Apple Squeeze to the FreshGrass Festival, only add to the region’s seasonal charm.

A long weekend in the Berkshires offers something for everyone: a morning hike up Mount Greylock, where fiery foliage stretches across five states; an afternoon apple-picking and cider-tasting at a local orchard and an evening in Lenox, whether that means lingering over a farm-to-table dinner with local wine or catching off-season programming at Tanglewood. Read on for the best places to stay, eat and explore on a Berkshires getaway.

Where to Stay

Canyon Ranch Lenox

• 165 Kemble St, Lenox, MA 01240

Housed on a historic 120-acre estate, Canyon Ranch Lenox is an all-inclusive wellness retreat that shines especially bright in autumn, when the landscape transforms into a blaze of reds, oranges and golds. Guests can fill their days with scenic hikes, forest bathing, cycling or yoga under the changing leaves before unwinding at the spa, a 100,000-square-foot sanctuary with seemingly endless treatments, a fitness center, an indoor pool and hydrotherapy experiences. The programming is equally impressive, with classes ranging from Pilates and barre to meditation and breathwork. Between activities, guests dine on gourmet, chef-crafted meals featuring seasonal ingredients (think chicken farro salad with crisp Granny Smith apples, burgers with house-made potato rolls, omelets with fresh-picked vegetables and artisan-baked breads), or retreat to one of the 126 rooms. 

This fall also brings something new to the getaway: outdoor treatment tents where guests can book Reiki, reflexology and other therapies as they bask in the brisk mountain breeze. A handful of themed retreats, like the Berkshires Fall Foliage Escape, make the case for planning a visit before the last leaves fall.

Red Lion Inn

• 30 Main St, Stockbridge, MA 01262

Dating back to 1773, the Red Lion Inn is one of the Berkshires’ most storied landmarks. With its white clapboard exterior and expansive rocking chair-lined porch, the inn anchors the small town of Stockbridge like something out of a Norman Rockwell painting. (Fittingly, his former studio, part of the Norman Rockwell Museum, is just down the street.) Inside, the inn leans into its colonial-era character. Expect narrow hallways creaking beneath wide-plank floors and walls adorned with patterned wallpaper, oil paintings and antique clocks. The same aesthetic extends to the 108 rooms and suites, most of which are attired with patterned wallpaper, four-poster beds and floral drapery.

Beyond the porch, a flora-filled courtyard serves as another central gathering spot for sipping coffees or cocktails. The main dining room serves classic regional fare (don’t miss the New England clam chowder) in an elegant, chandelier-filled setting outfitted with lavish red drapery and printed wallpaper. The casual downstairs tavern, reminiscent of an old English pub, offers ice-cold brews, hearty sandwiches and salads. Tucked even deeper below street level, the aptly named Lion’s Den speakeasy serves handcrafted cocktails and bar bites like charcuterie and smashburgers, and regularly hosts live music acts.

Tourists

• 915 State Rd, North Adams, MA 01247

In North Adams, just down the road from the galleries of Mass MoCA, sits Tourists, a 1960s motor lodge reimagined as an arty boutique retreat. Its design strikes a balance between rustic and hip, with cedar-clad exteriors and interiors—including 46 guest rooms and common spaces—that balance natural wood and warm textiles with vintage accents and pared-back furnishings. At the heart of the property, the main lounge glows around a roaring fireplace, flanked by vintage rugs, low-slung chairs and sofas layered with wool blankets. The riverfront getaway extends into an 80-acre forest campus dotted with sculptural installations and tranquil nooks, all linked by a striking suspension bridge. Housemade breakfast staples, such as brown-butter waffles, smoked salmon-topped bagels and gochujang cheddar scones, fuel days of museum-hopping or leaf-peeping.

Miraval Berkshires

• 55 Lee Rd, Lenox, MA 01240

Set on 380 acres in Lenox, Miraval Berkshires takes a more free-spirited approach to wellness than its neighbor, Canyon Ranch. The programming here blends curiosity and adventure. For example, mornings might begin with aerial yoga or ziplining through the trees, while afternoons could feature beekeeping workshops, equine therapy or a reflective walk through the meditation labyrinth. When the weather cooperates, the outdoor pool becomes a sparkling centerpiece, framed by flowers and towering trees. Like the rest of the resort, the 121 guest rooms and cottages evoke a sense of serenity with clean lines, soothing tones, natural woods and oversized windows that let in loads of natural light. 

The true star of the show is the Asian-inspired Life in Balance Spa, where treatments range from Ayurveda and Reiki to Thai massage and energy work. That global influence carries into the kitchen as well, with menus featuring saffron-lemon risotto, wild-mushroom rice bowls finished with local kimchi, and lion’s mane tacos.

What to Do

Tanglewood

• 297 West St, Lenox, MA 01240

Best known as the summer home of the Boston Symphony Orchestra, Tanglewood draws music lovers from across the country. Summer is the busiest season, with big-name concerts and picnics spread across the lawn. In the fall, the atmosphere shifts. While the crowds have thinned, the programming continues, with concerts, recitals and guest lectures keeping the calendar full. Even without an event, the grounds are worth visiting for their wide-open fields and scenic walking paths.

The Mount

• 2 Plunkett St, Lenox, MA 01240

The Mount, Edith Wharton’s former estate in Lenox, is a National Historic Landmark and a vivid reflection of the writer’s imagination, from its stately interiors to its sweeping terraces. Wharton designed the house and gardens herself in 1902, calling it her “first real home.” Today, the estate is best described as part museum, part outdoor escape. Visitors can step back in time with a guided tour through grand drawing rooms, roam through the lush, European-inspired gardens or wander along wooded trails that open onto breathtaking hillside views. Additionally, in nearby Pittsfield, literary lovers mustn’t miss Arrowhead—the home-turned-museum where Herman Melville penned Moby Dick. 

Lakeview Orchard

• 94 Old Cheshire Rd, Lanesborough, MA 01237

Perched in the rolling hills of Lanesborough, Lakeview Orchard offers a farm-to-table experience. Visitors can pick their own fruit—cherries in early July, raspberries and currants by mid-summer, blueberries through August, and apples once September arrives. Apple season marks the start of fresh cider, pressed on-site from the orchard’s own harvest. Beyond the fields, the bakery keeps visitors well-fed with scratch-made treats, including fan favorites like still-warm cider donuts plus a seasonal selection of fruit pies, turnovers, scones and whoopie pies. 

Hilltop Orchards

• 508 Canaan Rd, Richmond, MA 01254

Hilltop Orchards is part cidery, part winery and part outdoor playground. You can sip your way through a flight of Johnny Mash ciders, from classic New England styles to unexpected flavors like coconut lime. Book a tour to see the process up close, from apples pressed on the old-fashioned rack-and-cloth to cider aging slowly in oak barrels. Alternatively, savor one of the dozen-plus artisanal wines made right on-site.

The orchard isn’t just about drinking, though. Trails designed by John Morton loop through the property, winding past rows of apple trees and into the woods. Hike them in spring, summer and fall or snowshoe them in winter. Back at the farm, sit back and relax in an Adirondack chair with your drink of choice—best enjoyed with a hot apple cider donut.

Mass MoCA

• 1040 Mass MoCA Way, North Adams, MA 01247

Housed in a converted mill complex in North Adams, the Massachusetts Museum of Contemporary Art spans roughly 250,000 square feet across a constellation of brick buildings—an ideal setting for some of the most ambitious (and largest) contemporary art in the United States. An entire building is devoted to the Sol LeWitt wall-drawing retrospective, which covers nearly one acre of interior wall space. The museum also has large-scale installations by artists like James Turrell, including immersive light environments. Beyond the galleries, the experience extends into performing arts, with concerts, experimental theater, film screenings and even an annual bluegrass festival unfolding across its industrial courtyards and venues.

Mount Greylock State Reservation

• 30 Rockwell Rd, Lanesborough, MA 01237

At 3,491 feet, Mount Greylock stands as Massachusetts’ highest peak and one of the Berkshires’ most beloved landmarks. On a clear day, the summit rewards you with sweeping views across five states: Massachusetts, New York, Connecticut, Vermont and New Hampshire. Trails here run the gamut from leisurely woodland strolls to steep, rocky climbs that may leave your legs sore, though the views are more than worth it. Come autumn, the ridgelines blaze with fiery reds and golds, making Mount Greylock one of New England’s most spectacular spots for leaf-peeping.

Where to Eat and Drink

Berkshire Mountain Distillers

• 356 S Main St, Sheffield, MA 01257

Equal parts educational and convivial, Berkshire Mountain Distillers in Sheffield creates small-batch, award-winning spirits, from gin and bourbon to one-off experimental blends. Sample a tasting flight or settle in with a seasonal cocktail in the tasting room. If you’re curious about the craft, self-guided tours offer a behind-the-scenes look at the distilling process. When you’re done, it’s worth sticking around to explore the campus and wander the grounds, sip cocktails beneath the covered pavilion or cozy up by the fire pit.

Casita

• 1111 Mass MoCA Way, North Adams, MA 01247

Just steps from the MASS MoCA galleries, Casita is the kind of spot you wander into for a quick bite and somehow lose track of time. The menu is filled with playful riffs on Mexican staples, spotlighting ingredients sourced from local farmers, cider makers and fishermen. Mushroom empanadas arrive draped in pistachio mole, while street corn shows up in the form of pillowy gnocchi. Libations are mezcal-forward, with smoky cocktails that pair as easily with a plate of tacos as with a lingering conversation. There’s also a thoughtful lineup of natural wines and local beers. The vibe is relaxed but buzzy; a place where museum-hoppers and North Adams regulars trade stories across the same table, margaritas in hand.

Shots Cafe

• 27 Housatonic St, Lenox, MA 01240

In the heart of historic downtown Lenox, Shots Café is a go-to for a laid-back breakfast or lunch. With its central location and cozy, welcoming vibe, it’s the kind of place you’ll duck into more than once during a Berkshires stay. The menu covers the essentials (egg sandwiches, savory salads, hearty paninis), but the real draw is the pastry case. Expect a rotating selection of treats, including flaky croissants, chocolate éclairs and muffins coupled with savory selections like fresh-baked, veggie-loaded quiches, best enjoyed with a cappuccino or latte.

Dairy Cone

• 197 Tyler St, Pittsfield, MA 01201

Sometimes it’s the simplest spots that hit the sweetest note. Dairy Cone is a no-frills, family-run ice cream joint that has been slinging out frozen treats for decades, and it’s easy to see why. Go classic with vanilla or chocolate soft serve, or savor local favorites like black raspberry and coffee. The rainbow swirl (pictured) is tough to pass up, and it’s every bit as tasty as it is photogenic. Rounding out the menu are treats like fruity Dole Whip, frozen yogurt, over-the-top sundaes and extra-thick milkshakes.

Balderdash Cellars

• 81 State Rd, Richmond, MA 01254

The family-owned Balderdash Cellars is as much a neighborhood hangout as it is a working winery. Guests gather on the lakefront lawn to sip wine, linger over conversation, and take in the views, especially in the fall, when the trees surrounding the lake burst into vibrant colors. Adirondack chairs and picnic tables dot the grass, and with no reservations required or accepted, the whole place carries a relaxed, come-as-you-are vibe. Live music and food trucks often round out the scene, giving it more of a backyard feel than a formal tasting room. The wines (whites, rosés and reds) have cheeky names, such as the “Truth Serum” chardonnay and “Liquid Courage” cabernet sauvignon.

Frankie’s

• 80 Main St, Lenox, MA 01240

This cozy Italian eatery in downtown Lenox leans into classic Italian-American comfort, from the red-and-white-checkered tablecloths and dim lighting to the warm, attentive service. The menu is loaded with old-school favorites like chicken parm, seafood fra diavolo and lasagna, all made with a Berkshires twist thanks to locally sourced ingredients. The drink list includes wine, beer and creative cocktails like the aptly named “Under the Tuscan Sun” (tequila with lime, grapefruit bitters, cilantro simple syrup, and a Tajín rim). A full vegan menu ensures everyone at the table is covered.