The most populous state in the New England region is also home to some of the most sought-after resorts. Cape Cod is one of the biggest draws but the Northeastern state is also home to captivating vacation islands, easy-on-the-eye college towns, the wooded hills of the Berkshires, handfuls of important historic sites, and that’s not forgetting its fun and trendsetting capital, Boston! Here are my all-time favorite spots I’d love to share…
1. Cape Cod 
On the eastern shore of Massachusetts is the arm-shaped headland of Cape Cod. It tops this list as it’s an eternally popular beach destination and I’m personally a huge fan of this gorgeous spot. It’s a summer haven with calm waters, a gorgeous sandy beach, cute boutiques and guest houses and tropical fauna.
Nestled close to the quaint town of Provincetown is Cape Cod’s renowned Race Point Beach. Surf or swim or just kick back and take it all in! Brimming with water activities, a warm climate, glorious dunes and scenic beauty it’s a gem of a place!
2. Nantucket
This is a gorgeous vacation destination in the form of a beautiful very small island located around 30 miles off the coast of Cape Cod! As well as lots of upscale boutique accommodations to choose from there are plenty of other great reasons to make the trip here.
My favourite highlights include beautiful dune-backed sandy beaches, striking cedar-shingled buildings, pretty manicured gardens and a charming main town known for its wharves and cobblestoned streets. Here you’ll also find great restaurants, high-end boutiques and steepled churches.
3. Boston Harbor 
A natural harbor on Massachusetts Bay, the Boston Harbor is located adjacent to the city of Boston. Since its discovery in 1614, the harbor has been an integral part of American history. Meander along Boston’s Harborwalk or watch the stunning sunset, the harbor offers friendly public access to the water’s edge.
Explore the 13 islands of Boston Harbor accessible by ferry. Hike along the Spectacle Island or visit the historic Fort Warren of George Island, these beautiful islands offer a host of recreational activities with some majestic views of the Atlantic.
4. Martha’s Vineyard
To the south of Cape Cod is this seriously dreamy and popular summer destination for vacationers! The island of Martha’s Vineyards offers unspoiled natural beauty for a real retreat. With a scenic lighthouse, Greek revival houses and eye-catching beaches, this glacial origin island is only accessible by boat or air.
Full of hidden wonders, I would suggest trekking the Aquinnah Cliffs to witness some of the best sunsets. Formed by the glaciers millions of years ago, these epic clay cliffs are the best place for those seeking solitude. Enjoy the pristine harbor views in Edgartown or take a ride on the iconic Flying Horses Carousel, the islands offer a potent blend of history and charm!
5. The Berkshires
Nestled in the rolling hills between Boston and New York, the Berkshires is a land of strike contrasts. Renowned for its outdoor adventures and water sports, the Berkshires offers a great blend of natural scenery and cultural experiences.
I would recommend adventuring in the quaint towns of Lenox, Williamstown or witnessing the contemporary art in North Adams and Stockbridge.
6. Cambridge
Located across the Charles River from Boston is what is known as one of the best places to live in the state! From the world-renowned Harvard University to the city’s fantastic museums and clubs, Cambridge offers plenty of things to do and see.
I would highly recommend exploring the Harvard Art Museum with its eclectic exhibits and sculptures from the Middle Ages to the National historic site of the Longfellow House, visitors can enjoy the vibrant performing arts scene with fine dining.
Ander around the bustling epicenter of Cambridge, the iconic Harvard Square is packed with quirky boutiques, bookstores, and restaurants with a lively atmosphere.
7. Mohawk trail
Opened in 1914, the picturesque Mohawk Trail runs east and west across northern Massachusetts meandering through historic towns, scenic woodlands and dramatic vistas.
Stretching over 69-miles, this marveling byway spreads over 50,000 acres of land paralleling five major rivers gushing over the rocks. Hike along the Mohawk Trail State Forest or indulge in water sports on the Millers River and Deerfield River Valley, the landscape offers an ideal place for leaf-peeping.
I would recommend stopping at the Shelburne Falls or the picturesque cottage towns of North Adams and Williamstown, this captivating trail houses some of the rich heritage buildings with contemporary arts and historic places.
8. Cape Anne
This is a relatively undiscovered destination within an hour’s drive from Boston is the Cape Anne. Named after the honor of Queen Anne, Cape Anne is home to the nation’s oldest working fishing port.
Explore some of the oldest working art galleries in Gloucester or check out the historic ship museums in Essex, this rocky cape offers unspoiled beaches with miles of gorgeous coastlines. I would recommend trying the local cuisine (exotic fried clams anyone?) or strolling around the quaint antique stores here.
9. Rockport
At the tip of Cape Anne’s peninsula stands the historic coastal town of Rockport. The heart of Rockford is the iconic seaside element, Motif Number 1, a classic red fishing shack built in the 1800s and an inspiration for so many artists.
As you explore the town, you’ll find myriad works of art on the Bearskin Neck and Dock Square. Sunbathe or dip or feet in the calm waters of Front Beach and Cape Hedge Beach or watch the historic lighthouses from Loblolly Point, Rockford has the perfect fuel for exploration.
I would suggest visiting the scenic conservation area in the Halibut Point State Park and watching the magical sunsets, in my opinion, Rockford is a coastal gem of New England.
10. Plymouth Bay
Along the western shore of Cape Cod Bay lies the protected landform of Plymouth Bay. The Plymouth Rock is where the Mayflower pilgrims came ashore in 1620 and helped found the nation.
Enjoy the tranquillity of nature in the Nelson Memorial Park and Brewster Gardens or splurge on the stunning beaches, Plymouth Bay is the best place for a detox.
Art lovers can visit the Jenney Museum and the Pilgrim Hall Museum for an unmatched collection of iconic exhibits. I would then suggest spoiling yourself at the Plymouth Bay Winery with locally grown berries and grapes!
11. Wayside Inn Grist Mill
A legendary district in Sudbury, the Wayside Inn not only houses the oldest operating inn in the country, the Wayside Inn but also the iconic Grist Mill, the Wayside Inn Grist Mill.
Built under the direction of automobile giant, Henry Ford in 1929, this water-powered mill uses grinding stones to produce fresh cornmeal and wheat flour.
In my opinion, it’s a perfect spot to soak up some history and sunshine, this quaint landmark has been an inspiration for renowned author Henry Wadsworth Longfellow. Adjacent to the mill is the Martha-Mary Chapel and the schoolhouse built by Henry Ford.
12. Massachusetts State House
Nestled in Beacon Hills of Boston, the Massachusetts State House has held the legislative and executive branches of the state since 1798. Designed by Charles Bulfinch, this architectural marvel is a designated National Historic Landmark.
The magnificent setting of the building and its intricate details are a true reflection of colonial times. Observe the Senate and the House of Representatives while they convene or watch the stunning murals with exquisite details, this impressive gold-domed building is where the past meets the present.
13. Mount Greylock
Western Massachusetts’s scenic mountain, Mount Greylock is the state’s highest point in the Berkshire Mountains. Rising at 3,489 feet, mount Greylock is the most beautiful mountain in the eastern U.S. Explore Mount Greylock State Park with myriad species of fauna and flora.
With a network of extensive trails, Mount Greylock offers the best outdoors for all levels of hiking. Marvel at the scenery of lovely farmlands and countryside with a scenic drive.
Standing atop the peak is the Veteran War Memorial, a beautiful tribute to the armed forces. I would recommend watching out for the miles of stunning countryside or relaxing on the lawn (in the summer)!
14. Harwich Garden
A popular vacation spot, the mesmerizing town of Harwich lies in the Barnstable County. With welcoming shorelines, lovely gardens, lush greens and fun little shops and galleries, this New England town offers plenty of things to see and do. Known for its role in the story of America, the Harwich Port offers miles over rivers and marshes with walking trails and tidal creeks.
I would recommend discovering the beautiful blooms of the Cape Cod lavender farm and the Doane Park which is home to stunning greens or dipping your toes in the sunny beaches and Pleasant Lake, I think this seaside town is a charming and precious gem!
15. Concord
An affluent Boston suburb with preserved open spaces and treasured buildings, the town of Concord is located in Middlesex County. Visit the Ralph Waldo Emerson House and the Concord Museum, the historical delights with the most prized collections of Americana.
Commemorating the opening battle of the American Revolutionary War, the Minute Man National Historic Park and the Old North Bridge houses and protect the battlefields and structures of the American Revolution. A designated iconic landmark, the Walden Pond offers ample hiking and recreational opportunities for adventure seekers.
16. Nobska Lighthouse
Often called the Nobska Point Light, the Nobska Lighthouse is a Falmouth icon and an essential part of the history of the Cape Cod town. A beacon of light since 1829, this light station shines on the confluence of Vineyard and Nantucket Sounds.
Refreshing sea breeze, clean beaches and surrounding environment, Nobska Road brims with recreational activities and vivid antique shops and art galleries. I would suggest touring the historic building, picnicking or exploring the shorelines of Nobska Point the iconic light station!
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Gary Nunn – Videographer, photographer and writer
Gary is an award winning full time professional photographer and videographer with too much wanderlust for his own good. Fueled by strong coffee, you’ll often find him wandering well off hiking trails in search of interesting photographic subjects or scenery to video. Self taught and with the use of pioneering digital techniques, he quickly built up a strong client base and has worked with many prestigious organizations, including GQ, BBC, London Fashion Week, Grazia, Sky, Metro, Vogue Italia. He specializing in evocative images of people, places and cinematic videography and his goal is to make the viewer look twice and engage. As well as a penchant for good design, travel, starting up new businesses, the ketogenic diet and Hungarian Vizslas, he also has a huge affection for Chicago, Bucharest, Scandinavia, Croatia and absolutely everywhere in Italy. Find Gary on Instagram, Twitter, Facebook, YouTube or his Website.
Hotel Reviewing Experience – Asked by many tourist boards and many high-profile travel brands to formally review hotels including Germany Tourist Board, Expedia, Eviivo, Visit Morocco, and Wild in Sight Safaris. Also travelled around the world scouting out and reviewing all the most unique hotels in the world, check out our Instagram page for photos. Listed as a top UK travel journalist.
