9 Incredible Vacation Spots In Massachusetts
From the cobblestone streets of Boston to the windswept beaches of Cape Cod and the tranquil beauty of the Berkshires, Massachusetts offers a wealth of history, culture, and natural charm. Explore revolutionary landmarks, world-class museums, picturesque coastal towns, and serene island escapes, each with its own story to tell. Whether you are tracing the footsteps of the Pilgrims in Plymouth, admiring the arts in Lenox, or whale watching in Gloucester, the Bay State is full of unforgettable experiences for every traveller.
Boston
Boston, the capital of Massachusetts and seat of Suffolk County, sits on Massachusetts Bay, an arm of the Atlantic Ocean. Though small in size for a major city, over a quarter of its area is water, including parts of the Charles River, Boston Harbor, and the Atlantic itself. Rich in history and culture, Boston offers a perfect blend of old-world charm and modern attractions. Start with the Freedom Trail, a 2.5-mile path connecting 16 historic sites that bring the American Revolution to life. Along the way, you will encounter museums, churches, meeting houses, and even a historic ship, each telling a piece of Boston’s pivotal role in U.S. history.
For shopping, dining, and lively entertainment, head to Faneuil Hall Marketplace and Quincy Market. World-class street performers and local musicians fill the air with music and laughter, while over 25 eateries serve Boston favorites, from fresh seafood to decadent desserts. Music lovers should not miss the Boston Symphony Orchestra. This world-renowned ensemble has performed across the globe, and its home performances are a cultural highlight of the city. Art enthusiasts will find treasures at the Museum of Fine Arts, home to one of the world’s most comprehensive collections. Together, these attractions showcase Boston’s unique ability to honor its storied past while embracing a vibrant present.
Salem
Famous for its maritime history as the birthplace of the National Guard, and for the infamous Witchcraft Trials of 1692, Salem blends historic intrigue with a lively, walkable downtown. Each year, over a million visitors explore its preserved architecture, world-class museums, eclectic shops, and diverse dining. With easy public transit, including its own ferry, Salem is as convenient as it is captivating. A great starting point is the Salem Witch Museum, which offers two immersive exhibits. The first recounts the 1692 trials through life-sized sets and dramatic narration, transporting visitors to 17th-century Salem. The second, Witches: Evolving Perceptions, explores European witchcraft trials, shifting cultural portrayals of witches, and the broader history of persecution in America.
For scenic beauty, head to Salem Harbor, once one of the busiest international ports in colonial America. In the late 18th and early 19th centuries, goods from across the globe arrived here, including ceramics, spices, and dyes. Today, the harbor offers stunning sunsets best enjoyed from Pickering Wharf. Literature lovers will enjoy the House of the Seven Gables, a National Historic Landmark made famous by Nathaniel Hawthorne’s novel of the same name. Guided tours, gardens, and seaside lawns make it a charming stop for both history and relaxation. Art and culture enthusiasts should not miss the Peabody Essex Museum, founded in 1799 by Salem sea captains. The museum houses an extraordinary global collection of art, history, and culture, including a 200-year-old Chinese home, alongside ever-changing exhibitions.
Cambridge
Situated on the north bank of the Charles River, just across from Boston, Cambridge is steeped in American history and world-class education. Settled in 1630 as New Towne and renamed for Cambridge, England, in 1638, the city became the site of Harvard College, now Harvard University. Harvard Square, the historic heart of the city, has long been a hub for culture, scholarship, and political thought. Cambridge also played a notable role in the American Revolution: in 1775, George Washington assumed command of the Continental Army here at Cambridge Common. A visit to Harvard University offers a walk through nearly four centuries of history. Harvard Yard, listed on the National Register of Historic Places, includes landmarks like Wadsworth House, once Washington’s headquarters during the 1775 siege of Boston, as well as Widener Library, and the iconic statue of John Harvard.
For science and art lovers, the Harvard Museum of Natural History showcases over 12,000 specimens, from dinosaur skeletons to rare minerals. Highlights include the Blaschka “Glass Flowers,” incredibly detailed glass plant models crafted between 1886 and 1936. History and leisure meet at Cambridge Common, a public park with Revolutionary War ties, historic cannons, a children’s playground, and shaded picnic areas. To unwind, stop at Tilde Café & Wine Bar, a cozy, locally-focused space offering artisan coffee, natural wines, charcuterie boards, and light fare sourced from nearby producers.
Provincetown
Perched at the sandy tip of Cape Cod, Provincetown has long been tied to a spirit of freedom, from the Pilgrims’ first landing to its vibrant role as a welcoming destination for the LGBTQ+ community. Over time, fishermen, whalers, Portuguese immigrants, artists, and writers have all shaped its eclectic character. Today, visitors come for its natural beauty, cultural energy, and colorful personality. Art lovers will find plenty to explore. The Provincetown Art Association and Museum (PAAM), over a century old, houses more than 3,000 works by 700+ artists, many with local ties. Admission is free on Friday evenings after 5 p.m. from May to November.
For outdoor adventure, dune tours showcase the sweeping sandscapes of the Peaked Hill Bars Historic District. Guides share the history, ecology, and creative legacy of the dunes, which have inspired generations of artists. Sunset tours, beach dinners, and boating excursions add to the experience. Whale watching, which began here in 1975, remains one of Provincetown’s signature activities. From April to October, visitors can spot humpback, right, and fin whales on excursions with companies like Dolphin Fleet or Captain John Boats out of Plymouth. No trip is complete without a meal at the Lobster Pot, a beloved local institution since 1979. With fresh seafood, views of Provincetown Harbor, and warm Cape Cod hospitality, it is as iconic as the neon lobster sign above its door.
Martha's Vineyard
Just off the coast of Massachusetts, Martha’s Vineyard feels worlds away from the everyday rush. Known for its laid-back lifestyle, seaside cliffs, wildflower fields, and windswept beaches, the island offers a perfect mix of relaxation and charm. Visitors can savor fresh seafood and farm-to-table cuisine, explore quaint towns with unique shops and galleries, and soak in over 120 miles of shoreline. For dramatic scenery, head to Aquinnah Public Beach (Moshup Beach), where a short walk from the parking area leads to breathtaking views of the Gay Head Cliffs. The beach has seasonal restrooms, and daily parking is available in summer.
Dive into the island’s history at the Martha’s Vineyard Museum, which houses art, artifacts, oral histories, and photographs spanning centuries. Founded in 1922, the museum has grown into a cultural cornerstone, preserving and sharing the island’s stories with visitors from around the world. Shoppers will love Edgartown, the island’s retail hub. Main Street is lined with boutique clothing shops, art galleries, candy stores, and coastal outfitters, offering everything from summer wardrobe staples to perfect keepsakes. In Oak Bluffs, do not miss the iconic Gingerbread Cottages of the Martha’s Vineyard Camp Meeting Association. This colorful Victorian enclave, a National Historic Landmark, dates back to the 1800s and surrounds the iron Tabernacle, a centrepiece for religious, cultural, and community gatherings.
Nantucket
Known as “The Faraway Land” in the Wampanoag language, Nantucket lies 30 miles off Cape Cod. Just 14 miles long and 3.5 miles wide, this charming island is over 50% conservation land, offering pristine beaches, scenic trails, and a timeless coastal charm. Accessible by air or ferry, via the Steamship Authority or Hy-Line, there are many ways to get to and from the island. Jetties Beach is a family favourite, with calm waters, lifeguards in season, and easy access by bike, car, or the island shuttle. Its wide, flat shoreline is perfect for shell collecting, and amenities include restrooms, showers, a seasonal restaurant, and rentals for sailing, kayaking, and windsurfing. It also hosts the Boston Pops concert each August.
For a dose of maritime history, visit Brant Point Lighthouse, America’s second-oldest, built in 1746. Standing just 26 feet tall, it has guided mariners for centuries and is a beloved symbol for arriving ferry passengers. Tradition says tossing a penny into the sea when leaving ensures a return to the “Grey Lady.” The Nantucket Shipwreck & Lifesaving Museum honours the courageous rescuers who braved treacherous waters to save stranded sailors, telling tales of shipwrecks and survival that shaped the island’s seafaring legacy. For fresh flavors, stop by Bartlett’s Ocean View Farm, Nantucket’s oldest and largest family-run farm, now in its seventh generation. Pick up artisan sandwiches, cheeses, fresh bread, and desserts for the perfect beach picnic just a half-mile away.
Plymouth
Known as “America’s Hometown,” Plymouth sits on Plymouth Bay, 37 miles southeast of Boston. It was the site of the first permanent European settlement in New England, founded in 1620 by the Pilgrims who sailed on the Mayflower seeking religious freedom. Tradition holds that they landed on Plymouth Rock before building their first fort on Burial Hill, where Governor William Bradford and other early settlers are buried. Today, Plymouth blends deep history with scenic coastal beauty, making it a must-visit for history buffs and casual travellers alike. Heritage Museums & Gardens offers 100 acres of beautifully landscaped grounds, featuring flowering shrubs, trees, and seasonal blooms. Spring brings vibrant Dexter Rhododendrons, while summer and fall showcase lush gardens perfect for leisurely walks. For a glimpse into Indigenous history, check out the wetu, a traditional Wampanoag seasonal dwelling constructed of cedar saplings and bark or cattail reeds, reflecting the life of the Wampanoag people in southeastern Massachusetts for over 12,000 years.
Nature lovers can explore the nearby Duxbury Beach Reservation, a 4.5-mile stretch of pristine coastline. Lifeguarded swimming areas, walking paths, and bayside spaces for shellfishers, kiteboarders, and families make it ideal for a day outdoors, with stunning views of Cape Cod Bay and protected habitats for local wildlife. After a day spent wandering, dine at Martini’s Bar & Grill, a local favourite known for fresh, seasonal ingredients sourced from nearby farms. From Black Angus burgers to filet mignon, pasta, and house-made desserts, the menu offers something for every palate. Live jazz on Tuesdays and music on Saturday nights add to the vibrant atmosphere and round out the visit.
Gloucester
Located on the southern shore of Cape Ann, about 30 miles northeast of Boston, Gloucester is a historic maritime city with a rich fishing heritage. First mapped by Samuel de Champlain in 1605-06, the area was settled by colonists from Dorchester, England, in 1623 and incorporated as a town in 1642. Gloucester’s fishermen sailed from New England to Greenland and Iceland, and the Fisherman’s Memorial, a bronze statue overlooking the harbor, honors more than 10,000 mariners lost at sea. Over the centuries, Portuguese and Italian immigrants have contributed to the city’s cultural and maritime traditions, inspiring works like Rudyard Kipling’s Captains Courageous and Henry Wadsworth Longfellow’s The Wreck of the Hesperus.
Long Beach offers a classic New England shoreline experience. With soft sand, gentle surf, and postcard views of Thacher Island’s twin lighthouses, it is perfect for sunrise strolls, surfing, or relaxing by the water. A row of seaside cottages adds nostalgic charm to this iconic Cape Ann destination. For wildlife enthusiasts, Cape Ann Whale Watch sails aboard the Hurricane II, Gloucester’s largest and fastest vessel, offering close-up views of whales while educating visitors about these magnificent creatures and their habitat in Massachusetts Bay. History and innovation meet at the Hammond Castle Museum, built between 1926 and 1929 by inventor John Hays Hammond Jr., known as the “Father of Radio Control.” The museum blends medieval, Gothic, and French village architecture and houses stone archways, sarcophagi, grave markers, and an impressive lapidarium. Visitors can explore both historic artifacts and newly curated exhibits, making it a vibrant hub for history, art, and STEAM enthusiasts.
Lenox
Incorporated in 1767, Lenox is a scenic town in Berkshire County, Massachusetts, known for its arts, culture, and natural beauty. Every season draws visitors to enjoy its rolling hills, vibrant cultural scene, and outdoor activities. Tanglewood, the summer home of the Boston Symphony Orchestra since 1938, offers a quintessential Berkshires experience. Spread a blanket on the lawns of its 210-acre campus, enjoy a picnic, and listen as the music rises around you, whether a soaring cello solo or James Taylor strumming a familiar chord. Families, teens, and picnickers all share the magical atmosphere of this world-renowned venue.
Chocolate Springs is a must-visit for sweet lovers. Chocolatier Joshua Needleman crafts chocolate from scratch in rich, inventive flavours, from dark chocolate with caramelized hazelnuts to ganache infused with raspberry or spices. The café allows visitors to sip thick hot chocolate or sample whimsical treats to take home, a perfect stop after exploring nearby Kennedy Park. History and literature converge at The Mount, the Gilded Age home of Pulitzer Prize-winning author, Edith Wharton. Wharton wrote many of her best-known novels here, including The House of Mirth and Ethan Frome. Visitors can stroll the terraces, enjoy the gardens, and imagine the intellectual gatherings that inspired her work in the early 20th century.
From historic streets and revolutionary landmarks to charming coastal towns and serene islands, Massachusetts is a state where past and present coexist in vibrant harmony. Whether exploring Boston’s cultural treasures, strolling the scenic shores of Martha’s Vineyard, discovering the arts in Lenox, or experiencing the maritime heritage of Gloucester, each destination offers its own unique story. With so much to see, taste, and experience, the Bay State promises memories that last a lifetime.
