The Best Road Trip Route In Massachusetts Passes Stunning Coastal Scenes And Quaint Fishing Villages

As a resident of Salem, Massachusetts myself (and yes, there is a better time to visit Witch City for all the fall fun without hectic crowds), it would take me all day to sing the praises of my state's North Shore. While Cape Cod is known simply as "the Cape" to locals, it's not the only cape that the Bay State has to offer. Cape Ann is Cape Cod's northern counterpart, and when it comes to classic New England coastal charm, it measures up to southern Massachusetts in every way. 

It's impossible to escape that quintessential New England feel when it comes to visiting the four towns that make up Cape Ann: Manchester-by-the-Sea, Gloucester, Rockport, and Essex, the only one of the bunch that's technically located a bit inland. You can hit all four of these gems by driving the best road trip route in Massachusetts for classic coastal scenes and quaint fishing villages, and it will only take you about 40 miles to do it. Best of all, it all starts less than an hour north of Boston and Logan International Airport.

What you'll find in these vibrant coastal communities is nothing short of magic, and chief among the top attractions are beautiful nature reserves with unmatched views of dunes, bays, and open ocean. You can enjoy whale watching at the oldest port in the country, award-winning restaurants, and the birthplace of the fried clam. There is no shortage of shops, art galleries, and museums along this popular route, including the Cape Ann Museum, which features exhibitions that celebrate the area's maritime history. Finally, if you want to expand your imagination and pretend you've left the country, a medieval-style castle and a European-inspired estate provide an ultimate escape.

Beverly is a popular place to access Cape Ann, and I'd be remiss not to mention its proximity to Marblehead, an unsung town on the Massachusetts coast brimming with classic New England charm and history. Coastal scenic byway signs abound here, directing visitors toward Salem, where the history of the famous 17th-century witch trials drives the tourism of a vibrant modern city. From there, you can cross the Veterans Memorial Bridge to Beverly to begin your journey along the coast of Cape Ann, and it's just a 20-minute drive to your first stop. 

Manchester-by-the-Sea is known as the setting for the Oscar-winning movie of the same name, and also for the old-world charm of Singing Beach, a quaint stretch of sand featuring an original bathhouse built in the 1920s and a snack stand. The town also boasts the natural haven of Coolidge Reservation, which features a small pine and oak forest, a scenic pond, and a beautiful seaside lawn.

Less than 10 miles away is the historic city of Gloucester, with its beautiful beaches and world-class whale watching. America's oldest seaport has a variety of family-friendly beaches to choose from, including Good Harbor Beach, Wingaersheek Beach, and Stage Fort Park Beach. Spend a day enjoying the sun and sand, but it's a good idea to book parking ahead of time, as it gets crowded with both locals and visitors during the high season. For those who are more apt to enjoy an indoor activity featuring fascinating historical content, try the historic landmark of Beauport, the Sleeper-McCann House, or Hammond Castle, a unique medieval-style castle filled with artifacts boasting a real drawbridge and an interior courtyard with the technology to control its own weather.

Rockport is a scenic Massachusetts beach town with world-class art and cute shops. Walk to the end of Bearskin Neck for panoramic ocean views, and along the way, you'll find cute nautical shops and art galleries. When it comes to enjoying the area, activities like whale watching, sea kayaking, and exploring the nature trails on foot or by bicycle are just some of the many ways you can soak up the sea air, and you'll probably notice that many of the buildings here are unusually colorful, adding to the idyllic coastal views.   

Your scenic drive will come to an end in Essex, a close neighbor of Ipswitch, a beach town with scenic sand dunes and world-famous clams. In fact, Woodman's of Essex may be a no-frills seafood shack, but it claims to be the birthplace of the fried clam. TripAdvisor ranks it first among casual places to eat in Essex, and most reviewers are generous with their praise of the fried seafood, which is all completely gluten-free.

One of the chief attractions in the Essex area is the Crane Estate on Castle Hill, a luxurious, historic 2,100-acre estate that will make you feel like you're in Europe. This unbelievable property boasts loads of protected land and, like the Coolidge Reservation, it's owned and maintained by the Trustees of Massachusetts, who are committed to keeping this special place open for visitation. You can also hop on an Essex River Cruise to experience everything the beautiful coastal inlets have to offer.