It was an early-morning kayaking trip on a lake near Stockbridge, in western Massachusetts.

Our guide, Jim Czarnecki, suddenly pointed. Way up high on a shoreline tree, a golden eagle appeared to be enjoying the peace and quiet as much as we were. Conversations quickly faded, as we stared at this majestic bird. Presently, it soared off, leaving us quietly enriched. The experience simply underlined the absolute tranquility of the Berkshires. Czarnecki, whose company Taking Shape offers outdoor excursions throughout the Berkshires, was as delighted as we were by the sighting.

The locals in this part of western Massachusetts like to say nature sets the scene and culture steals the show. The Berkshires’ 32 villages and towns—many of them quintessential New England—are surrounded by lakes, rivers, forests and hills. Easily accessed from Boston and New York, wealthy folks have been coming here to unwind since the Golden Age of the 19th century, and their palatial summer homes are still called “cottages.”

Complementing the four-season joys of the outdoors, the Berkshires’ cultural treasures are also legendary. In Stockbridge, where Norman Rockwell lived from 1953 to his death in 1978, you’ll find more than 700 paintings and drawings at the outstanding Norman Rockwell Museum, along with plenty of insight on the man whose detestation of bigotry and social injustice is clearly illustrated in some of his 322 Saturday Evening Post covers, such as his famous “Do Unto Others As You Would Have Them Do To You.”

On a summer’s evening, Tanglewood is the place to be. At this summer home of the Boston Symphony Orchestra, performances on the sprawling wooded estate run through July and August. First-comers get seating under cover while the lawns accommodate up to 17,000 concert-goers—some bringing their own tables, chairs, and even chefs.

Other options for culture buffs include MASS MoCA, one of the largest contemporary art museums in the country, and the Shakespeare & Company theatre festival.

A Taste of the City

Boston is a city that most people never tire of visiting. Between colourful neighbourhoods steeped in history, its maritime flavour and an avant-garde approach to urban living, there’s plenty to enjoy time and again. There are certain things—weather and time permitting—that I like to do, from people-watching on Boston Common (a lovely patch of greenery that’s the oldest city park in the U.S.) to wandering through the Museum of Fine Arts, revisiting history along the four-kilometre Freedom Trail, or exploring the revamped waterfront. It’s easy to get around—on foot or via the T (the city’s expansive subway system). And, there’s always something new to discover.

In the historic Fort Point Channel neighbourhood, the story of how 342 chests of British tea, worth more than US$1,700,000 in today’s money, were dumped overboard is powerfully told at the recently-opened Boston Tea Party Ships & Museum. Live actors, two restored tea ships and interactive technology bring the Boston Tea Party to life, on the same body of water where it took place on December 16, 1773.

East of the Fort Point Channel, South Boston is one of the country’s oldest neighbourhoods. Once home to a tight enclave of working-class Irish, the 19th- and early 20th-century warehouses now house galleries, studios and lofts, and boutique hotels and trendy restaurants are becoming the norm, including Menton, the city’s only Relais & Châteaux restaurant, and Blue Dragon, an old diner turned hip Asian gastropub. For a light lunch, try the delicious quinoa and tofu salad, along with homemade raspberry seltzer, at Flour Bakery.

As Fort Point is also home to New England’s largest artist community, be sure to check out their art, crafts and design at Made in Fort Point (30 Channel Center Street).

Off to the Cape

Launched last summer, the CapeFlyer train service between Boston and Hyannis, Cape Cod, operates Friday to Sunday from Memorial Day to Columbus Day. It’s a great option, particularly if you make Hyannis your base, and there are various ways (ferry, bus or car rental) to travel farther up the Cape.

A short walk from the station, the John F. Kennedy Hyannis Museum provides an intimate perspective on the 35th president. Wandering through, it’s almost like turning the pages of a cherished family photo album—except the photos are on the walls, and a docent, instead of the album’s owner, provides her or his own unique take on the official information and captions. Photos range from a young Jack and his siblings frolicking on the beach to JFK and Jackie relaxing with their children at their beloved Hyannis Port retreat, to politically-themed photos that underline its role as the summer White House. The nearby Kennedy Legacy Trail visits 10 sites of importance to the Kennedy clan, including the St. Francis Xavier Church and the Hyannis Armory, where JFK accepted his presidential nomination.

For a break from history, relax over a creamy Cape Cod clam chowdah at Spanky’s Clam Shack and Seaside Saloon, located beside a dock where guys wearing T-shirts saying “Shut up and Fish” clamber aboard charter boats. Pain D’Avignon is a rather different culinary hot spot. Locals line up at lunchtime at this café-boulangerie to buy mouth-watering sandwiches (their bread is so good that it’s sold to hotels and restaurants within a 320-kilometre radius). Come evening, the café morphs into an intimate French bistro where an innovative menu offers the best available, featuring locally-grown produce and fresh-caught seafood wherever possible.

Above all, Cape Cod is known for its beaches and related activities, from ecotours to whale-, dolphin- and seal-watching cruises. Favourites include Nauset Beach, a 16-kilometre stretch of white sand on the Atlantic side and the bayside beaches in Dennis, Orleans and Brewster, where the water is generally warmer.

With so much on offer, a vacation in Massachusetts inevitably leads to a return trip. There’s always way too much happening to stay away for long.

Travel Planner

For activities and travel ideas, visit massvacation.ca. For destination updates and reviews from guest bloggers, visit the “MA Finds” blog at massvacation.com/blog.