Berkshire Museum 9 Min The Berkshire Museum is a rare mash-up of art, natural science, and history under one roof in downtown Pittsfield, about a 10-minute drive from The Yankee Inn. Fresh off a major renovation, the museum reopened in July 2026 with refreshed galleries and a new state-of-the-art aquarium. Read more Berkshire Botanical Garden 15 Min Founded in 1934, the Berkshire Botanical Garden is one of New England's oldest public gardens. Its 24 acres feature over 3,000 plant species across more than two dozen display areas, with an emphasis on plants that thrive in the Berkshire climate. It's a peaceful, beautiful place to spend a morning or afternoon, especially from late spring through fall when the gardens are at their peak. The garden also hosts year-round workshops, lectures, and seasonal events, including the beloved Harvest Festival each October. Read more Hancock Shaker Village 15 Min Once known as the "City of Peace," Hancock Shaker Village is one of New England's most fascinating living history museums — 20 original buildings spread across a 750-acre campus, anchored by the iconic Round Stone Barn that still stops visitors in their tracks. The Shakers called this place home for 179 years, and their devotion to simplicity, craftsmanship, and equality is palpable in every room. Explore the restored buildings, watch farming and craft demonstrations, stroll the grounds, and browse a collection of over 22,000 Shaker objects that bring the community's extraordinary legacy to life. Read more Jiminy Peak Mountain Resort 30 Min The Berkshires' premier four-season resort, Jiminy Peak keeps the mountain busy no matter what month you show up. In winter it's the largest ski and snowboard area in southern New England — 45 trails, three terrain parks, 1,150 feet of vertical drop, and one of the most extensive night skiing networks in the region, with 22 trails lit until 10pm. Come summer, the slopes give way to a full Mountain Adventure Park: a mountain coaster, alpine super slide, aerial adventure course, giant swing, rock climbing wall, and chairlift rides with sweeping views of Mount Greylock and the Jericho Valley. The on-site Country Inn, John Harvard's Restaurant and Brewery, and a year-round heated outdoor pool mean you never really need to leave — though the rest of the Berkshires is right at your doorstep when you're ready to explore. Read more Pleasant Valley Wildlife Sanctuary 5 Min Managed by Mass Audubon, this 1,400-acre sanctuary offers seven miles of well-marked trails winding through forests, meadows, and wetlands. It's one of the closest outdoor adventures to The Yankee, and there's something for every ability level, from the accessible boardwalk loop around Pike's Pond to the challenging hike up Lenox Mountain with panoramic views from the summit. Keep an eye out for the resident beaver colony, and if you're visiting in spring, ask about the salamander migrations. The sanctuary is open year-round and offers guided hikes, birding programs, and a popular summer nature camp for kids. Read more Venfor Hall Mansion and Gilded Age Museum 8 Min Ventfort Hall is a grand 1893 mansion right in Lenox, just a few minutes from The Yankee Inn, which now serves as a museum of the Gilded Age. With its hand-carved oak interiors and 90-foot veranda, it's one of the easiest and most atmospheric outings you can make from the inn. Read more Berkshire Scenic Railway Museum 18 Min The Berkshire Scenic Railway Museum preserves Western Massachusetts's railroading history at the beautifully restored 1903 Lenox Station, just a few minutes from The Yankee Inn. It's a small, friendly, volunteer-run museum and an easy stop for train lovers and families exploring Lenox. Read more Lebanon Valley Speedway 25 Min Lebanon Valley Speedway is a half-mile, high-banked dirt oval just over the New York state line, about a 40-minute drive from The Yankee Inn in Lenox. If you want a loud, family-friendly summer night out that's a little different from the Berkshires' usual arts-and-nature fare, a Saturday at 'the Valley' delivers. Read more Ashuwillticook Rail Trail 18 Min Its name comes from the Mohican word for "pleasant river between the hills," and the trail lives up to every syllable of it. Built on a former Boston and Maine Railroad corridor, this 14-mile paved path runs through the Hoosac River Valley between Pittsfield and Adams, hugging the shores of Cheshire Reservoir and the Hoosic River for much of the way with Mount Greylock presiding over the northern horizon. Flat, wide, and fully paved, it's one of those rare trails that works for everyone — cyclists, walkers, rollerbladers, families with strollers, and wheelchair users alike. Great blue herons, kingfishers, eagles, turtles, and the occasional muskrat keep things interesting along the wetland stretches, and in winter the trail converts into a quiet snowshoeing and cross-country skiing corridor. A visitor center in Adams and several well-placed picnic areas and restroom facilities make it easy to spend a full day out here. Read more Bousquet Mountain 4 Min Bousquet Mountain is one of the oldest ski areas in the country and the closest ski hill to Lenox, about a five minute drive from The Yankee Inn. It's a friendly, local mountain built for a straightforward day of skiing, snowboarding, or snow tubing, which makes it a great pick for families, beginners, and anyone who wants time on the snow without a long drive. Read more Bash Bish Falls 50 Min Massachusetts' tallest waterfall doesn't disappoint. Bash Bish Brook splits around a massive boulder at the crest and plunges some 60 feet in a dramatic V-shape into a deep, emerald pool below — framed on both sides by the steep walls of a gorge carved over millennia. Sacred to the Mohican people and later a muse for Hudson River School painters, the falls carry a mystical quality that photographs can't quite capture. Two trails lead to the viewing area: a short, steep half-mile scramble from the Massachusetts lot, or a gentler 1.5-mile stroll from the New York side through Taconic State Park — the latter is the better bet for families. Either way, wear sturdy shoes, keep to the designated viewing area, and let the sound of the falls do the rest. The Mount, Edith Wharton Cultural Center 10 Min Born into New York high society in 1862, Edith Wharton defied convention to become one of America's leading literary voices and the first woman to win the Pulitzer Prize. The Mount, her Lenox estate, is where that brilliance found a home. Designed and built by Wharton in 1902, the house embodies the principles outlined in her influential book, The Decoration of Houses — and she considered it her first true home. Restored gardens include an Italian walled garden, a formal flower garden, an alpine rock garden, a lime walk, and sweeping grass terraces, all designed by Wharton herself with the same precision and elegance she brought to her writing. Interpretive exhibits throughout the 42-room house explore Wharton's literary legacy, her humanitarian efforts, and the lives of the servants who shared the estate with her. Beyond the house tours, The Mount engages visitors through author talks, exhibitions, writer residencies, and a landscape designed for reflection and discovery. Ghost tours running from July through October add a delightfully unexpected layer to this already extraordinary place. Norman Rockwell Museum 15 Min This museum houses the world's largest collection of original Norman Rockwell artwork, with over 500 paintings, drawings, and illustrations that capture American life with warmth and humor. The 36-acre campus overlooks the Housatonic River Valley and includes Rockwell's original studio, relocated here from Stockbridge village. The museum is open year-round and regularly hosts visiting exhibitions focused on American illustration. Allow a couple of hours to take it all in, and don't skip the studio tour. Bistro Zinc 7 Min Bistro Zinc offers a polished and inviting dining experience, with a thoughtfully designed space that balances energy and comfort. The menu blends classic French-inspired dishes with creative touches, appealing to a wide range of tastes. Backed by a professional and attentive team, Bistro Zinc stands out as a well-regarded choice among Lenox’s dining scene. Mount Greylock 1 Hr At 3,491 feet, Mount Greylock is the highest point in Massachusetts — and it earns the title. On a clear day, the summit offers views stretching up to 90 miles across five states, with the Berkshire valleys rolling out in every direction below. The mountain has long drawn literary pilgrims: Hawthorne, Thoreau, and Melville all found inspiration here, and Melville is said to have seen the outline of a great whale in its ridgeline while writing Moby-Dick. For hikers, over 70 miles of trails wind through a landscape that shifts dramatically from northern hardwood forest at the base to a rare boreal spruce and fir summit — like traveling from Pennsylvania to Maine in a single afternoon. Those who'd rather skip the climb can drive the scenic auto road straight to the top, where the 93-foot Veterans War Memorial Tower stands watch and the historic Bascom Lodge offers meals and overnight stays from late May through October. Downtown Lenox 7 Min Downtown Lenox is a quintessential New England village with a personality all its own. Walker Street and Church Street are lined with independent boutiques, galleries, and restaurants ranging from casual farm-to-table spots to fine dining. It's the kind of place where you can browse a bookshop, pick up locally made gifts, and still have time for coffee and a pastry before dinner. In the summer months, the village buzzes with concert-goers heading to Tanglewood, while fall brings a quieter charm alongside stunning foliage. Many of our guests mention that the walkability of downtown Lenox is one of the highlights of their trip. Jacob’s Pillow 25 Min Home to America's longest-running international dance festival, Jacob's Pillow has been bringing world-class dance to the Berkshires since 1933. Set on a 220-acre National Historic Landmark campus, the festival runs for ten weeks each summer and features more than 50 dance companies from around the globe. Performances happen on both indoor and outdoor stages, and many of the outdoor events are completely free. Between shows, you can explore the archives, catch an artist talk, or simply enjoy the wooded campus. It's a must for anyone who appreciates live performance. Naumkeag 15 Min Built in 1884 for prominent New York attorney Joseph Choate, this stunning 44-room Gilded Age estate sits on 48 acres in the heart of Stockbridge, with sweeping views of Monument Mountain framing every garden path. The eight acres of terraced garden rooms — including the Afternoon Garden, Rose Garden, Chinese Garden, and Linden Walk — were transformed over 30 years by landscape architect Fletcher Steele and Choate's daughter Mabel, resulting in one of the most imaginative designed landscapes in America. The crown jewel is the Blue Steps: a cascading staircase of azure fountain pools flanked by white birch trees that feels, impossibly, like it belongs in a dream. Steepletop Reserve 40 Min For those who want to escape into the Berkshires wilderness, truly, Steepletop Reserve delivers one of the most rewarding outdoor experiences in the region. At 1,230 acres, it is the Berkshire Natural Resources Council's largest reserve, and it feels every bit of it — remote, raw, and remarkably peaceful. Five miles of marked and maintained trails plus three miles of wood roads, all on easy grades, make it ideal for hiking, birdwatching, snowshoeing, and cross-country skiing. The two main loops, Louise Lane and Edie's Way, wind past historic stone walls, old cellar holes, and brook crossings, while the wetlands around Harmon Brook draw abundant wildlife. The reserve's woods range from managed young-forest habitat to a small patch of unusually old forest in the northwest corner — a rare find in New England. The name itself nods to a time when the forest was sparse enough that the New Marlboro church steeple was visible from this hillside. No facilities, no crowds — just miles of quiet forest waiting to be explored. Kennedy Park Trails 5 Min Right in the heart of Lenox, Kennedy Park covers 500 acres of hardwood forest crisscrossed by nearly 15 miles of groomed trails. Originally home to the grand Aspinwall Hotel (you can still find the ruins), the park was preserved in the 1950s and is now one of the most popular spots in town for hiking, trail running, mountain biking, and cross-country skiing in winter. Trails range from easy carriage roads to more challenging single-track, and several lookout points reward you with sweeping views of the valley. You can access the trails from downtown Lenox, right next to the Church on the Hill, or from the Arcadian Shop on Route 7. Grab a map before you go because the trail network is extensive and it's easy to lose your bearings. Read more District Kitchen & Bar 9 Min District Kitchen & Bar offers a lively and welcoming atmosphere, delivering a well-executed dining experience even during peak hours. The menu features expertly prepared dishes, including standout steak options, alongside attentive and courteous service. With its energetic setting and efficient staff, it remains a popular and reliable choice in the Berkshires. Stockbridge Bowl 15 Min Also known by its original Mahican name, Lake Mahkeenac, Stockbridge Bowl is the kind of place that makes a Berkshires summer feel complete. The 372-acre lake is ringed by forested hills and dotted with kayaks, sailboats, and canoes from morning to dusk — and with Tanglewood perched on its northern shore, you might catch the faint sound of an orchestra drifting across the water on a summer evening. A public boat ramp and the Town Beach on the southeast shore make it easy to spend the day here, whether you're casting a line for bass and trout, paddling the six miles of shoreline, or simply picnicking on the grass with a view that doesn't quit. Come winter, ice fishermen set up their huts on the frozen surface — proof that the Bowl has a loyal following in every season. Frankie's 6 Min Frankie’s delivers a warm, romantic dining atmosphere paired with classic Italian favorites. The menu highlights freshly prepared dishes like house-made pasta and traditional entrées, complemented by attentive and efficient service. With a focus on quality ingredients and a welcoming ambiance, Frankie’s stands out as a reliable dining option in the Berkshires. Williamstown 45 Min Tucked into the northwest corner of the Berkshires, Williamstown is a classic New England college town built around Williams College. The real draw for visitors is the Clark Art Institute, a world-class museum with an exceptional collection of Impressionist and American art set on a stunning 140-acre campus designed by Pritzker Prize-winning architect Tadao Ando. The grounds include reflecting pools, hiking trails, and pastoral views that make it worth visiting even if you're not heading inside. Williamstown is also home to the renowned Williamstown Theatre Festival each summer. Pair a visit with a stop at MASS MoCA in neighboring North Adams to make a full day of art in the northern Berkshires. Mass MoCA 45 Min If you're up for a day trip, MASS MoCA is well worth the drive. One of the largest contemporary art museums in the country, it's housed in a beautifully converted 19th-century factory complex spanning 16 acres. The galleries are enormous, which means the art here is often immersive and monumental in scale. Beyond the visual art, MASS MoCA hosts live music, film screenings, and performing arts events throughout the year. The campus also has a brewery (Bright Ideas), a cafe, and a gift shop, so you can easily make a full day of it. The scenic drive through the northern Berkshires is a bonus. Tanglewood Amphitheatre 10 Min The summer home of the Boston Symphony Orchestra since 1937, Tanglewood is one of the most celebrated outdoor music venues in the country. The season runs from late June through early September, with performances ranging from classical symphonies and chamber music to popular artists like James Taylor and Carrie Underwood. Bring a blanket and a picnic for a lawn seat, or enjoy the legendary acoustics inside the Koussevitzky Music Shed. Even outside concert season, the grounds are worth a visit for a quiet stroll through the Berkshire hills. The Clark Art Institute 45 Min One of the great art museums of New England, the Clark houses a stunning collection of Impressionist and American masterworks — Renoirs, Monets, Winslow Homers, and John Singer Sargents — in a setting so beautiful it feels almost unfair. The 140-acre campus of meadows, woods, and walking trails was envisioned as a sanctuary in the woods, and the architecture — including Tadao Ando's dramatic Clark Center with its three-tiered reflecting pool — lives up to that vision completely. Budget extra time to hike up Stone Hill for panoramic views of Williamstown and the surrounding Berkshires; the art inside is world-class, but so is everything outside. Great Barrington 25 Min Great Barrington has been called one of the best small towns in America, and once you visit, you'll understand why. The walkable downtown is packed with farm-to-table restaurants, independent bookstores, vintage shops, and craft breweries. It has a creative, slightly bohemian energy that sets it apart from other Berkshire towns. Foodies will want to check out the Berkshire Co-op Market and SoCo Creamery, while hikers can tackle nearby Monument Mountain for a rewarding summit with valley views. It's a great half-day trip from The Yankee, especially if you pair it with a stop in Stockbridge on the way. Stockbridge 15 Min Immortalized in Norman Rockwell's paintings, Stockbridge is one of the most picturesque small towns in the Berkshires. Main Street feels like stepping into a different era, with the historic Red Lion Inn anchoring the center of town. Beyond the Rockwell Museum, you'll find Naumkeag (a stunning Gilded Age estate with gardens designed by Fletcher Steele), the Stockbridge Library and Museum, and charming shops and cafes. The town is especially magical during the holidays, when its annual Stockbridge Main Street at Christmas celebration brings Rockwell's famous painting to life. Ramblewild Adventure Park 30 Min Not your average day out. Set on nearly 1,000 acres of undeveloped forest in Lanesborough, Ramblewild is one of the most impressive aerial adventure parks in the country — built entirely within an 11-acre hemlock grove, with the tree canopy keeping things cool and shaded even on the hottest summer days. Eight tree-to-tree trails of varying difficulty wind through over 150 elements: rope ladders, cargo nets, suspended bridges, zip lines, and a heart-stopping 80-foot ravine crossing that can be tackled either by zipline or a 200-foot suspension bridge overhead. Trails are rated ski-slope style, so first-timers and seasoned climbers alike will find their level. A Basecamp trail opens the adventure to kids as young as four, while the park's most challenging black diamond routes will humble even the fit and fearless. Sustainably designed — not a nail in a single tree — and open April through October. The Olde Heritage Tavern 6 Min The Olde Heritage Tavern captures the charm of a classic New England tavern, with rustic interiors and a lively, welcoming atmosphere. The menu focuses on comforting pub favorites, including well-prepared burgers and crisp, satisfying sides. This is a perfect place to enjoy hearty fare in the Berkshires. Eric Carle Museum 1 Hr Founded by Eric and Barbara Carle in 2002, The Carle holds more than 20,000 works of art representing over 300 picture book artists — from Maurice Sendak to Leo Lionni — making it the only museum in the world dedicated entirely to this art form. Three rotating galleries, a hands-on art studio, a reading library, and an auditorium hosting live performances and author appearances make it as much a place to create as to admire. It's a genuinely magical stop for families, but just as rewarding for any adult who grew up with a favorite picture book — which is to say, everyone. Alta 7 Min Alta offers a refined dining experience centered around seasonal ingredients and carefully crafted dishes. The menu reflects New England’s flavors with a modern approach, complemented by thoughtful presentation and attentive service. With a strong focus on quality and detail, Alta stands out as a notable restaurant in the Berkshires. High Lawn Farm 10 Min Some stops you stumble upon; High Lawn Farm is the kind you plan your afternoon around. A third-generation, family-owned, 100% Jersey dairy farm nestled into the rolling hills of Lee, it's been producing some of the Berkshires' finest dairy since the 1920s — and the quality shows in every scoop. The ice cream is legendary: at 16% fat and 30% overrun, it's about as dense and creamy as ice cream gets, with flavors like Purple Cow and Lemon Poppy Seed drawing repeat visitors all summer long. The on-site Farmstead Creamery Shop carries the full line — milk, butter, artisanal cheeses, and more — and the sweeping mountain views from the lawn make it easy to linger over a cone or a cheese board at the picnic tables. The Calf Barn and Milking Barn are open daily year-round, and getting up close with the Jersey calves is a highlight for visitors of all ages. A simple, genuine, utterly Berkshires kind of stop. Mario's 15 Min Mario's brings the warmth of an Italian kitchen to every plate — from handmade pastas and wood-fired classics to cocktails that make you want to linger just a little longer. The vibe is exactly what you'd hope for: candlelit, convivial, and unhurried. The kind of place where a Tuesday dinner feels like a special occasion.