Jiminy Peak is a great Berkshire ski day — easy to get to, well-run, and a fun option whether you’re brand new to skiing or just looking for a smooth, no-stress mountain day. The trails are consistently well-groomed, the lifts are efficient, and the overall vibe is friendly and upbeat without feeling overwhelming. It’s also a strong choice for families or mixed-skill groups, since there’s enough variety for everyone to have a good time.

Weekends can get busy, so arriving earlier is the move if you want shorter lines and more laps. Overall, it’s a classic winter go-to that delivers a really enjoyable day on the mountain.

Tanglewood Music Center is the iconic summer home of the Boston Symphony Orchestra nestled in the woods of Lenox, MA, known for world-class concerts and a lively festival atmosphere year-round—with summer being its highlight. From beloved traditions like James Taylor’s Independence Day weekend performances to standout summer shows featuring Ziggy Marley, “Weird Al,” Jason Isbell, and Cynthia Erivo, Tanglewood blends classical brilliance with contemporary stars in one unforgettable Berkshires setting. 

A Berkshire classic and a seriously fun night out, Shakespeare & Company brings world-class theater to Lenox year-round. The company puts on a mix of Shakespeare favorites, modern plays, and special productions, all performed with high energy and a professional feel that makes it easy to enjoy—even if you’re not usually a theater person.

Shows take place across a beautiful campus with both indoor theaters and outdoor stages, which gives the whole experience a uniquely Berkshire vibe (especially on a summer evening). It’s a great way to mix something cultural into your trip without it feeling stuffy or overly formal. Pro tip: grab dinner in town beforehand and make it a full night out.

One of the Berkshires’ most iconic historic estates, The Mount was once the home of Pulitzer Prize–winning author Edith Wharton. Tour the elegant Gilded Age mansion, explore the beautifully designed gardens and wooded walking paths, and check out rotating exhibits and seasonal events throughout the year. It’s a perfect mix of history, architecture, and a peaceful afternoon outdoors. 

Step back into the Berkshires’ Gilded Age at this grand 1890s mansion, known for its stunning architecture, elegant rooms, and rich local history. Guests can tour the beautifully preserved interiors, learn about the families who once summered here, and explore rotating exhibits and seasonal events that bring the era to life. It’s a great stop for anyone who loves historic homes, design, or a classic Lenox afternoon activity. 

One of the most iconic cultural stops in the Berkshires, the Norman Rockwell Museum is home to the world’s largest collection of the artist’s original paintings and illustrations. It’s an easy, feel-good visit (perfect for a relaxed afternoon), with galleries that walk you through Rockwell’s work, storytelling, and his connection to the region. The property itself is beautiful too — think rolling hills, peaceful walking paths, and great spots to take a breather outside. Don’t skip the gift shop, either — it’s one of the best around for unique prints, books, and Berkshires-inspired souvenirs. 

If you’re looking for something big, bold, and totally different, MASS MoCA is one of the most memorable day trips in the Berkshires. Set inside a massive renovated factory complex, this contemporary art museum is known for its larger-than-life installations, immersive exhibits, and constantly changing galleries — the kind of place where you can walk into a room and suddenly feel like you’re inside the art. Even if you’re not usually a “museum person,” it’s incredibly fun to explore because there’s always something surprising, interactive, or unexpected around the corner. Plan to spend a couple hours (or more if you take your time), and don’t be afraid to wander — it’s part museum, part adventure.

MASS MoCA is also home to Solid Sound, Wilco’s bi-annual music festival that brings major talent to the museum’s outdoor stages and turns the whole campus into a high-energy weekend experience. It’s a perfect all-season option too — especially on a rainy day, snowy afternoon, or anytime you want a break from the outdoors without losing the Berkshire vibe.

A perfect mix of world-class art and Berkshire scenery, The Clark is one of the most peaceful (and impressive) day trips you can take from Lenox. The museum is known for its beautiful collection of classic European and American works, plus rotating exhibitions that always feel fresh and thoughtfully curated. Even if you’re not trying to spend an entire day in galleries, it’s an easy place to enjoy at your own pace — calm, spacious, and never overwhelming.

What really sets The Clark apart is the setting: a stunning modern campus surrounded by rolling hills, walking trails, and wide-open views that make it feel more like a retreat than a traditional museum. It’s a great all-season option — ideal for a cozy winter afternoon, a rainy-day plan, or a sunny day when you want to pair art with a scenic walk outside.

A perfect outdoor escape just minutes from town, Pleasant Valley is a go-to spot for an easy hike, a peaceful walk, or a quick nature reset. The sanctuary has miles of well-marked trails that wind through woods, wetlands, and open fields, with plenty of chances to spot birds and local wildlife along the way. It’s great for all ages and activity levels — whether you’re looking for a short stroll or a longer loop with a little elevation. Bring good walking shoes, take your time, and don’t be surprised if you end up staying longer than planned. 

If you’re up for a classic Berkshire adventure, Bash Bish Falls is the waterfall hike everyone should do at least once. The trail is a scenic walk through the woods that leads to a dramatic, multi-tiered waterfall crashing into a rocky pool below — it’s one of the most impressive natural spots in the region and totally worth the drive. Expect some uneven terrain and a bit of a workout near the end, so wear sturdy shoes and plan for a little mud after rain. It’s especially beautiful in summer and early fall, and it’s a great “half-day” outing when you want fresh air, big views, and a memorable photo stop. 

An immersive environmental art sanctuary where nature, sculpture, and gardens are woven together into a peaceful outdoor experience. Guests wander winding paths past whimsical installations, stonework, water features, and hidden artistic details, all designed to encourage reflection and slow exploration. It’s part sculpture garden, part nature walk, and entirely one-of-a-kind—ideal for a calm afternoon outdoors or anyone looking for something quietly magical in the Berkshires.