Sometimes we just need to get away, change our surroundings for a bit, and gain a different perspective on life. Even if it’s just traveling within our own backyards, like on a Massachusetts road trip. If you’ve never explored Cape Ann, Massachusetts, we put together a short and sweet road trip to guide you. You’ll see some incredible scenery and visit some of the best of what this rocky cape has to offer.

This short and sweet road trip in MA is just over 26 miles. You can follow the route and stop at several points of interest by using our interactive map. Let’s get started!

Cape Ann is a rocky cape in the northeastern part of Massachusetts. It's comprised of the towns of Essex, Manchester-by-the-Sea, Gloucester, and Rockport along with Ipswich.
Google Maps
Start your journey in the town of Essex at Stavros Reservation. Part of The Trustees, this reservation sits atop a hill where you're guaranteed jaw-dropping views of both Crane Beach and the Essex River estuary.
Essex, MA, USA
Stavros Reservation, 1-15 Island Rd, Essex, MA 01929, USA
Jackie User/AllTrails
After you take a short hike and enjoy the views, if you are looking for more fun things to do in MA, head into town for some shopping and dining along Main Street. Learn more about what you can do in Essex.
Next on this MA road trip, we head south to Manchester-by-the-Sea. The first stop here is the incredibly scenic Tucks Point where you can take in views of the harbor.
12 Tucks Point Rd, Manchester-by-the-Sea, MA 01944, USA
Manchester-by-the-Sea, MA 01944, USA
Bill Girolamo/Google
A stop at Manchester-by-the-Sea's Singing Beach is mandatory while you're in town. Walk along the sand and listen to the noises it makes under your feet. It's utterly fascinating!
119 Beach St, Manchester-by-the-Sea, MA 01944, USA
Yaniv Kovalski/Google

Related Stories

The Most Affordable Massachusetts Road Trip Takes You To 4 Stunning Sites For Under $100

The Most Affordable Massachusetts Road Trip Takes You To 4 Stunning Sites For Under $100

 Yankee Candle Village Is An Inexpensive Road Trip Destination In Massachusetts That's Affordable

Yankee Candle Village Is An Inexpensive Road Trip Destination In Massachusetts That's Affordable

 This Bargain Hunters Road Trip Will Take You To Some Of The Best Thrift Stores In Massachusetts

This Bargain Hunters Road Trip Will Take You To Some Of The Best Thrift Stores In Massachusetts
We continue our road trip in MA to Gloucester where you can spend some time at the alluring Hammond Castle. Built in the 1920s, this castle once belonged to a prominent inventor.
Gloucester, MA, USA
80 Hesperus Ave, Gloucester, MA 01930, USA
JOAQUIM DEARAUJO/Google
Now a museum, you can take a self-guided tour and stroll its stunning grounds with water views.
After Hammond Castle, hit the road and head into town where you'll see the Fishermen's Memorial. Gloucester is a busy port city filled with beautiful beaches, excellent seafood restaurants, and gorgeous scenery. Set aside enough time to explore all of these fun things to do in MA before heading off to Rockport.
The Fishermen's Memorial, Gloucester, MA 01930, USA
Karen/Flickr
The quaint town of Rockport is next on your MA road trip. While you're here, you may as well stop at Motif #1, one of the most photographed spots in Massachusetts.
Rockport, MA, USA
Bradley Wharf, Rockport, MA 01966, USA
Maudib/ iStock / Getty Images Plus via Getty Images
Another point of interest in Rockport, albeit a quirky one, is the Paper House. Constructed (mostly) of paper, this house is one-of-a-kind and a must-see on your Massachusetts road trip.
52 Pigeon Hill St, Rockport, MA 01966, USA
Pria Priyanka/Google
As part of one of the best road trips in MA, a trip to Rockport would not be complete without stopping at Halibut Point State Park. Take a short, easy hike through the forest, by the quarry, and to the coast. It's so picturesque, you'll want to spend as much time here as possible.
Halibut Point State Park, Gott Ave, Rockport, MA 01966, USA
Julian Malcolm/Google

 

Are you excited to take one of the best road trips in MA? Let us know about your favorite places on Cape Ann in the comments!

If you would like to extend this Massachusetts road trip a bit further, you can always head to Ipswich and stop by Castle Hill at the Crane Estate as well as Crane Beach.

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

More to Explore

Getting to Know Massachusetts

Rachel Raimondi | April 24, 2023

What are the most scenic towns in Massachusetts?

Now that you've taken in a few towns as part of an MA road trip, make plans to explore some more of the most scenic towns in Massachusetts:

  • Hadley: Located in Hampshire County, this town is known for open-field farming, a technique that is extinct almost everywhere else. Among the many great spots here include Skinner State Park, the Silvio O. Conte National Fish and Wildlife Refuge, and New England Falconry.
  • Newburyport: This Essex County town is located right on the coast. Be sure to schedule visits to Maudslay State Park, the Custom House Maritime Museum, and the Parker River National Wildlife Refuge.
  • Concord: The Battle of Lexington and Concord, one of the most significant battles in American history took place in this Middlesex County town during the Revolutionary War. Make some time to see Minute Man Historical Park, Orchard House, and the Old Manse.

 

What are the best beaches in Massachusetts? 

When the weather is nice, head out to some of the best beaches in Massachusetts:

  • Mayflower Beach: You’ll find this stretch of sand on Cape Cod Bay in Dennis. There are 15 miles of shoreline to take in, with surfing being one of the most popular activities.
  • Herring Cove Beach: Another beach on Cape Cod, this one is in Provincetown. This spot is a great option for those who want to avoid other crowded beaches in the area. Just be aware that it is clothing optional.
  • Wingaersheek Beach: Located in Gloucester, this beach is on the Annisquam River. Enjoy swimming and sunbathing along the .6-mile beach. You can also fish, bike, and hike in the area.

 

What is Massachusetts known for?

Want to know more about The Bay State? Find out just what Massachusetts is known for:

  • Dunkin’ Donuts: Today, you can find this coffee and donut chain all over the world, but the very first one opened up in Quincy in 1950. And it’s still open today.
  • Salem Witch Trials: In 1692, over 200 people were accused of witchcraft in Salem, with more than a dozen of them being convicted and then executed. Today, you can visit the city and learn all about the facts (and fiction!) of this time in history.
  • The Boston Tea Party: Another historical event in Massachusetts, in late 1773, colonists protested the British government’s tea tax by dumping 92,000 pounds of tea into the Boston Harbor.

Related Articles