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Things to do in
Rockport, Massachusetts

Rockport, Massachusetts

Our most recommended things to do in Rockport, Massachusetts

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

1. Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

Start by downloading the Action Tour Guide app, which will function as your personal tour guide, audio tour, and map. Purchase one tour per car, not per person. Everyone listens together! Start a journey through the less-explored part of Massachusetts. Discover scenic beaches and historic towns as you drive, listen to the stories provided on the tour app, and stop for photos throughout the tour whenever you like. Begin the tour in Gloucester. When you drive, the app will provide instructions on how to use it. Then, head toward State Fort Park where you will hear about the Tablet Rock. From there, move on to the Fisherman’s Wives memorial and learn about its significance. Proceed on to the Fisherman’s Memorial over the Blynnman Canal Bridge before stopping for a stroll at Gloucester HarborWalk. Enjoy the view of the sea and pay a visit to the Maritime Museum, if you want. Next, see whales from the Cape Ann Whale watchpoint before discovering one of the oldest colonies in the U.S., Rocky Neck Art Colony. Make further stops at Niles Beach, Beauport Mansion, Eastern Point Lighthouse, Good Harbor Beach, and Pebble Beach. After Pebble Beach, you will be approaching Rockport before beginning the return journey to Gloucester. This part of the tour has some trivia and interesting spots to keep you engaged. On the way back, pass Halibut Point State Park and Harvey Reservation. If you want, you can take a break at Plum Cove Beach after the park. The tour then concludes at the Goose Cove reservation.

Boston: Salem and North Shore Private Guided Tour

2. Boston: Salem and North Shore Private Guided Tour

Embark on a private guided tour from Boston to Salem and the picturesque North Shore. Journey northward along the Atlantic Coast and stop in several seaside towns to explore their maritime heritage, pristine beaches, charming streets, and historic homes. Start with pickup from your accommodation and travel to the town of Salem. Discover the real stories behind Salem’s most infamous event, the Salem Witch Trials, at the sites where they occurred. Stop at Salem cemetery where several notable residents, including a notorious judge who presided over the Salem Witch Trials, are buried. You can also choose to visit The House of the Seven Gables, the Salem Witch Museum, and Essex Street, Salem’s vibrant downtown district. Next, venture to the Cape Ann peninsula, which includes idyllic Manchester-by-the-Sea, known for its beaches and upscale boutiques, and Gloucester, a bustling port with historic lighthouses and thriving art scene. Admire the postcard-perfect village of Rockport, a perfect place to enjoy ocean views, listen to the waves crashing on the shore, and see the most-painted building in America, Motif No. 1. After a day of exploration, relax on the return journey to Boston, with drop-off at your accommodation.

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Frequently asked questions about Rockport, Massachusetts

What top attractions are a must-see in Rockport, Massachusetts?

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Other Sightseeing Options in Rockport, Massachusetts

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What people are saying about Rockport, Massachusetts

Overall rating

4.3
(4 reviews)

I was lucky enough to take this trip with my mother for Memorial Day weekend and have beautiful weather. We both thoroughly enjoyed it and learned so much from the narrator. We were able to take our time and enjoy every sight and sound around every corner. Highly recommended!!!

This was the first time that I used this guide and it was very helpful for our drive. Instead if just driving and looking around we were informe about what we were seeing with a lot if descriptors. Made the trip much more interesting.

It was a little confusing learning how to use the app however we saw places that we would never have seen if we hadn’t use the app so glad we did this.

Interesting stories and facts but the directions were kind of hard to follow. We were guessing which way to go at some of the places.

it took us to places we wouldn't have even know were there, off the regular scenic highway. Was a lovely way to spend a day!