With 7 million residents and nearly 30 million annual visitors, Massachusetts is rich in history but modern in outlook. Locals and visitors alike are drawn to its stunning fall foliage, dramatic coastal shoreline and charming, picturesque villages. Its nickname, “The Bay State,” refers to the original settlements along Cape Cod Bay, while its name is a word from the Massachusett tribe meaning “at or about the great hill.” (The Great Blue Hill region is just south of present-day Boston.)
While not the very first European settlement in North America (that honor goes to the Spanish, in St. Augustine, Florida) or even the first British settlement (Jamestown was founded in what’s now Virginia 13 years earlier), Massachusetts is still home to an impressive number of “firsts” in the nation and the world. It all started in 1620 when the Puritans arrived in Massachusetts aboard the Mayflower. The first Thanksgiving was celebrated in 1621, soon followed by the country’s first public park and first public school. The state’s innovations continued with the invention of the typewriter and — by some accounts — the computer.
Massachusetts is also no stranger to celebrity: It was home to an impressive roster of notable figures, including four U.S. presidents; numerous Revolutionary War-era heroes like Paul Revere, Benjamin Franklin, Samuel Adams and John Hancock; and beloved authors such as Theodor Geisel — more famously known as Dr. Seuss — Edgar Allan Poe, Emily Dickinson, Henry David Thoreau and Louisa May Alcott.
“In Massachusetts, welcoming and belonging aren’t just values — they’re really part of who we are every day,” said Julie Arrison-Bishop, director of marketing at Massachusetts Office of Travel and Tourism. “For visitors, there’s the walkable charm of Boston, fresh seafood on the coast, and diverse neighborhoods across the entire state. Every experience is infused with authentic local color and a kind of a dynamic spirit in our communities. If you’re an outdoorsy person, there are mountain trails, or you can head out on the water. If you’re a beach person, you can enjoy a beach day. Our museums are world-class. And, in addition to the big city of Boston, there are so many wonderful smaller cities and small towns to choose from.”
This year and the next will be an especially attractive time to visit because Massachusetts will be celebrating its pivotal role in the Semiquincentennial, the 250th anniversary of the founding of the United States, in 2026.
Boston
Rich in history and boasting a vibrant arts scene, thrilling sporting events, and great dining and nightlife, the cultural and financial capital of New England is an ideal destination for groups of every type. While locals may affectionately refer to Boston as “Beantown,” the Algonquian Tribes called the peninsula Shawmut, which means “living waters.” The Puritan colonists who settled the city in 1630 named it after a market town in Lincolnshire. Boston has more than its share of firsts and visiting them is a fun way for groups to explore the city.
The Freedom Trail connects 16 historical sites across a 2.5-mile walking route and links many of Boston’s “firsts.” Boston Common, America’s oldest public park, serves as both the trail’s starting point and a central gathering place. Along the way, visitors encounter America’s first public school, Boston Latin School, founded in 1635, and the site of the first public library. Faneuil Hall, known as the “Cradle of Liberty,” hosted revolutionary meetings before the Boston Tea Party. The trail also leads to the USS Constitution, the world’s oldest commissioned naval vessel that is still afloat. The city also claims the first subway system in America. Opened in 1897, “the T” is still a great way for groups to get around while exploring the city.
Boston’s culinary reputation extends far beyond baked beans, and visitors should definitely sample the traditional New England clam chowder at Union Oyster House. America’s oldest continuously operating restaurant since 1826, it’s a must-stop for foodies. A slice of Boston cream pie at the Omni Parker House Hotel is de rigueur as well. For sports fans, Boston holds the distinction of hosting the first World Series in 1903, and Fenway Park provides an iconic baseball experience as the oldest baseball stadium still in use. It’s been home to the Red Sox since 1912.
The Berkshires
Artistic sophistication, outdoor adventures and a farm-to-foodie culinary scene are just a few of the highlights to be found in the rolling hills of western Massachusetts, where the Berkshires combine world-class performing arts with small-town New England charm. Tanglewood, the summer home of the Boston Symphony Orchestra, hosts classical music concerts under the stars, but the iconic venue also features comedians, popular artists like Jon Batiste and James Taylor, and movie screenings with soundtracks performed by the Boston Pops.
The Berkshires have long lured creatives, and artistic attractions extend beyond the concert halls. In Stockbridge, the Norman Rockwell Museum houses works by the beloved illustrator. An impressive collection of Impressionist paintings is on display at The Clark Art Institute in Williamstown. More modern tastes will appreciate the cutting-edge contemporary installations at MASS MoCA in North Adams. Housed in a converted industrial complex, it’s one of the country’s largest centers for contemporary visual art.
Beyond cultural attractions, the Berkshires offer natural beauty with hiking trails through old-growth forests leading to scenic overlooks, which are exceptionally stunning when autumn sets the trees ablaze in a riot of colors. Mount Greylock, the state’s highest peak, provides views across three states. The towns of Lenox and Stockbridge offer elegant lodgings and inventive dining, and the apple cider donuts at Guido’s Fresh Marketplace are not to be missed.
Plymouth
Playing a pivotal role in American and Protestant history, Plymouth is a must on any Massachusetts itinerary. While forever linked to the Pilgrims who established their settlement here in 1620, Plymouth has also grown into a dynamic destination that weaves together educational discovery, coastal beauty and contemporary culture.
“This is a great time to visit Plymouth — it offers so much for such a great price point,” said Lea Filson, president and CEO of See Plymouth. “This is where history actually happened to help create the foundation of America.”
The town’s most famous landmarks draw visitors from around the world. Plymouth Rock marks the legendary landing site of the Mayflower passengers, while the meticulously crafted Mayflower II replica allows guests to step aboard and experience the Atlantic crossing that changed history. The Plimoth Patuxet Museums bring the past to life through immersive exhibits that showcase both 17th-century English Colonial life and the rich heritage of the Wampanoag people, the region’s original inhabitants.
Plymouth’s coastal setting provides a stunning backdrop for exploration. The harbor and surrounding waters offer opportunities for scenic walks, boat tours and whale-watching adventures. Beach lovers can choose between the bustling atmosphere of White Horse Beach or seek solitude at Plymouth Long Beach. Inland, Myles Standish State Forest beckons with a network of trails winding through pine forests and around pristine ponds, perfect for hiking, cycling and nature retreats.
The town’s contemporary side flourishes in its downtown district, where art galleries, specialty shops and restaurants create a vibrant cultural scene. Local chefs showcase the region’s abundant seafood alongside innovative international flavors. Throughout the year, festivals and special events bring the community together.
Cape Cod
The windswept Cape Cod peninsula offers 400 miles of pristine coastline — everything from dramatic cliffs to gentle bay beaches. The Cape’s 15 towns each have their own personality, but Provincetown captures the area’s artistic spirit best. Here, visitors can climb the Pilgrim Monument for panoramic views then stroll Commercial Street’s galleries and eclectic shops. The bohemian atmosphere creates an energy that’s been attracting writers, painters and free spirits since the early 1900s. Long famed as a wholesome playground for the wealthy, Cape Cod continues to draw celebrities of all stripes.
A visit wouldn’t be complete without indulging in the Cape’s culinary seafood traditions. Visitors will want to tuck into a lobster roll at one of the countless clam shacks dotting Route 6A, the scenic Old King’s Highway that winds through historic villages like Sandwich and Brewster. These weathered establishments, many family-owned for generations, serve up fried clams, fish and chips, and creamy New England clam chowder that tastes exactly as it should. Travelers shouldn’t miss the chance to watch the fishing boats unload their daily catch in Chatham or Wellfleet, where they can often buy oysters and scallops directly from the harvesters.
The Cape’s natural beauty extends far beyond its beaches. Cape Cod National Seashore protects 44,000 acres of stunning landscape, including the otherworldly Marconi Beach dunes and the serene Great Island Trail in Wellfleet. Cycling the Cape Cod Rail Trail gives travelers access to cranberry bogs, salt marshes and hidden ponds that reveal the area’s diverse ecosystems. For those drawn to the water, sailing remains a cornerstone of Cape Cod culture, with everything from casual day sails out of Barnstable Harbor to the prestigious Figawi Race that draws competitive sailors from across New England each Memorial Day weekend.
