Best Things to Do in Massachusetts
While Boston and Cape Cod often steal the spotlight, Massachusetts is full of hidden corners that offer charm, history, and tranquility far from the usual tourist trail. After exploring the Bay State on many trips (often while staying with my in-laws who live there), I’ve discovered some gems that provide a more authentic taste of New England. I hope you’ll love them too.
1. Norman Rockwell Museum
I thought this was such a delightful cultural attraction — a charming blend of fine art, storytelling, and the pastoral beauty of the Berkshires. The museum sits on a rolling hillside with lush lawns and sweeping views, making it just as much a destination for its outdoor setting as for its world-class collection inside.
It was about a 2.5-hour drive west from Boston, and I spent a full day in Stockbridge exploring the museum galleries, wandering the scenic grounds dotted with sculptures, and pausing at Rockwell’s own historic studio, which has been relocated to the property. We spent a night at The Red Lion Inn.
2. Peabody Essex Museum
Peabody Essex Museum was an engaging mix of world-class art, global history, and striking architecture right in the heart of a historic New England seaport. The museum is a treasure trove of maritime artifacts, Asian export art, contemporary installations, and even entire historic houses relocated and preserved on the grounds.
It was just a 40-minute drive north of Boston to Salem, where I spent a day wandering the light-filled galleries, stepping into the 200-year-old Yin Yu Tang Chinese House, and enjoying the rotating exhibits that range from fashion to contemporary photography. The museum’s sleek modern wing opens into a bright atrium filled with natural light — a perfect spot to pause between exploring.
3. Old Sturbridge Village
Old Sturbridge Village is a living museum that brings early 19th-century New England to life with incredible authenticity. Spread across a large, pastoral landscape, the village is dotted with period homes, working farms, mills, shops, and costumed interpreters who demonstrate everything from blacksmithing to open-hearth cooking. It felt like stepping directly into the 1830s, surrounded by the sounds of horses’ hooves, the scent of wood smoke, and the rhythm of traditional crafts.
It was about a 1.5-hour drive west from Boston to reach Sturbridge, where I spent the day wandering through the village green, chatting with interpreters about daily life two centuries ago, and pausing to watch demonstrations of traditional farming. Seasonal events — like maple sugaring in early spring and harvest fairs in autumn — add extra layers of atmosphere.
4. Hancock Shaker Village
Hancock Shaker Village, nestled just outside Pittsfield, felt like a lesson in simplicity. I thought this was such a serene and soulful historical attraction — a beautifully preserved Shaker settlement where the simplicity of design, harmony with nature, and sense of community are still palpable. With its rolling fields, heirloom gardens, and iconic round stone barn, the village radiates a kind of quiet elegance that makes wandering the grounds feel both calming and inspiring.
It was about a 2.5-hour drive west from Boston into the Berkshires, where I spent two nights at 3-star Berkshire Mountain Lodge, exploring the historic buildings, watching costumed interpreters demonstrate traditional Shaker crafts, and walking the farm paths among heritage breeds of sheep, oxen, and chickens. The balance of working farm, museum, and spiritual history makes it a uniquely immersive place.
5. The Clark Art Institute
I thought The Clark Art Institute was such an elegant and uplifting cultural attraction — a world-class art museum set amid the rolling hills and woodlands of the Berkshires. The Clark blends a superb collection of European and American masterworks with striking modern architecture and expansive walking trails, creating a destination that feels equally about art, landscape, and reflection.
It was about a 3-hour drive west from Boston to Williamstown, stayed at 4-star The Williams Inn, where I devoted a full day to exploring the museum’s airy galleries, enjoying Renoir, Degas, and Homer side by side, and pausing often to admire the way the glass-walled modern wings frame views of meadows and mountains. Outside, I strolled the campus trails through forest and fields, soaking in the quiet natural beauty that complements the art inside.
6. The House of the Seven Gables
On the rocky waterfront of Salem, Massachusetts, I stepped back into the 17th century at the House of the Seven Gables — a brooding colonial mansion immortalized by Nathaniel Hawthorne’s novel. The timber-framed gables, creaking floors, and hidden staircases whispered centuries of stories, blurring the line between history and fiction.
Just a short walk from downtown Salem, near my hotel for two nights The Salem Inn, the site is more than the house itself: gardens blooming with roses and herbs lead down to the sea, and the visitor center weaves in Hawthorne’s life, works, and ties to the region.
Inside the mansion, I climbed the secret staircase tucked between walls, peered out leaded windows toward Salem Harbor, and lingered in rooms filled with period furnishings that evoked the harsh beauty of Puritan New England.
7. New Bedford Whaling Museum
In the historic seaport of New Bedford, Massachusetts, I immersed myself in the city that Herman Melville once called the “city of whalers.” The New Bedford Whaling Museum doesn’t just preserve maritime history — it plunges you into the salt-stung world of whaleships, harpooners, and global voyages that once defined America’s whaling capital.
Inside, I stood beneath the immense skeletons of a blue whale, humpback, and sperm whale suspended from the ceiling, their sheer size humbling. I traced the arc of whaling history through intricate scrimshaw carvings, oil paintings of tempestuous seas, and the colossal half-scale model of the whaleship Lagoda, large enough to climb aboard and imagine setting sail around Cape Horn. From the museum’s rooftop deck, the view of New Bedford Harbor connected past and present — fishing vessels bobbing where whalers once launched into the unknown. I stayed two nights at New Bedford Harbor Hotel.
8. Boston
Arriving in Boston felt like stepping into a city where every brick has a story — from the cobbled lanes of the Freedom Trail to the sleek glass skyline along the harbor. My stay at The Merchant, a boutique hotel in the heart of downtown, set the tone: modern comfort tucked inside a 19th-century building, perfectly blending old and new just like the city itself.
By day, I wandered through Boston Common and along Beacon Hill’s gaslit streets, then detoured through the bustling waterfront to watch ferries cut across the harbor. Each neighborhood felt like a different layer of Boston’s long history, stitched together with a distinctly modern energy.
One afternoon, craving something casual and lively, I ducked into El Pelón Taquería near Fenway. A plate of spicy carnitas tacos and fresh guacamole became the perfect fuel before weaving through the Red Sox crowds and soaking in the buzz of game day.
Conclusion
When I was based in NYC for 10 years, Massachusetts met me with painted villages, windswept harbors, and museums where silence spoke volumes. Every stop, from Shaker simplicity to seafaring drama, offered a different way to slow down and listen. I always find something new to discover when I visit my relatives who live in Massachusetts. For me it's all about seeing old places with new eyes.
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Booking Checklist
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4. Book your tours on Viator or Get Your Guide.
