Our most recommended things to do in Gloucester, Massachusetts

Gloucester: Scenic Cape Ann & Rockport Self-Driving Tour

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

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.

Liberty, Freedom, and Revolution: American Tours Bundle

2. Liberty, Freedom, and Revolution: American Tours Bundle

Discover the history of the American Revolution on a private self-guided walking and driving tour. Explore the freedom trail of Boston, Harborwalk, and more at your own pace with an audio guide. You will receive the download instructions after booking. Download the app and start the tour with your mobile phone as your guide. You will hear about the history, and the battles fought on the grounds.  Walk in the shoes of the Founding Fathers on the Freedom Trail and hear how the first sparks of revolution flew in Boston. Learn about the Sons of Liberty and uncover the truth about misunderstood events like the Boston Massacre. Next, reach Boston’s Harborwalk and revisit the fiery lead-up to the American Declaration of Independence. Stroll along the waterside and know about the dramatic protest called the Boston Tea Party and get a chance to visit the site. Afterward, head to the famous towns Lexington and Concord. Follow the route of an impossible battle between the American military and the British redcoats. Find out how the Americans turned the tide, and hear what it all meant in the fight for American independence. Then head to Valley Forge, where General George Washington faced some of his toughest challenges. Here, you will explore the remains of Washington’s 18th-century camp and hear the harrowing tale of how frigid temperatures, starvation, and desertion nearly pulled the American army apart. Finally, you will tour Philadelphia, where the Declaration of Independence was first signed. Hear stories about Ben Franklin and the other revolutionaries who called this city home. See the iconic landmarks like the famous Liberty Bell and Elfreth’s Alley, maintained just as it was in the 1700s.

Ultimate Boston Self-Guided Walking Tours Bundle

3. Ultimate Boston Self-Guided Walking Tours Bundle

Start in the city of Boston and walk in the footsteps of Revolutionary War heroes. Hear the story of Paul Revere’s Midnight Ride and relive the fight for American Independence with a self-guided walking tour of Boston’s Freedom Trail. Immerse yourself in the stories of the American Revolution, the Boston Tea Party, and the Sons of Liberty as you stroll along Boston’s scenic Harborwalk. Uncover Boston's historic and storied past while enjoying its beautiful harbor views between South Station and Long Wharf. Then, travel to the city of Cambridge outside Boston and explore the heart of Harvard University's campus at Harvard Square. Use the app to take a self-guided walking tour that covers must-see campus sights like the John Harvard Statue, Widener Library, and former dorm rooms of famous alumni like Bill Gates, Mark Zuckerberg, Natalie Portman, and more. Next, discover Cape Ann with a self-guided driving tour along the scenic waterfront. Enjoy the vistas, beaches, and natural beauty of the New England coastline at your own pace. Visit the famous Fisherman's Memorial, beautiful Beauport, all while diving into the stories of Massachusetts of days past. Shifting the scene to Salem, begin at the Salem Visitor Center. Learn about the Salem Witch Trials at the dedicated memorial and the Old Burying Point Cemetery. Stop by historic spots like the Old Town Hall, the Joshua Ward House, and Gedney House. Marvel at the Witch House and end your tour at The House of the Seven Gables, immersing yourself in the haunting history of Salem's Witch Trials.

Massachusetts Self-Guided Driving and Walking Tours Bundle

4. Massachusetts Self-Guided Driving and Walking Tours Bundle

Get to know the most famous Massachusetts attractions using this self-guided tour, which comes with a guide, an audio tour, a map as well as animated videos at some of the stops. In your own time and at your own pace, visit attractions such as Harvard Square, Plymouth, Martha’s Vineyard, and more. Begin your action-packed day by downloading the self-guided tour, and familiarize yourself with your digital guide. Make your first stop Harvard’s storied campus. Hear how the school got its start and how it evolved from a tiny college into one of the most prestigious institutions in the world. Then, head to the Freedom Trail to walk in the shoes of the United States' Founding Fathers. Hear how the first sparks of revolution flew in Boston and how those sparks became an inferno. Feel the revolution come alive as you pass sights like the church where Paul Revere’s famous lanterns once hung. Next, immerse yourself in the ship-rigging, ale-drinking, shanty-singing days of Colonial Boston on Boston’s Harborwalk and revisit the fiery lead-up to the American Declaration of Independence. Admire harbor views and visit the site of the Boston Tea Party. Continue by following your app to the most haunted spots of the city and hear popular ghost stories. Walk through graveyards, execution sites, and more while hearing hair-raising tales of the unquiet dead. After, head to Salem, and learn the truth behind the infamous Witch Trials. Turn the clock back even further in Plymouth, the town founded by Pilgrims fresh off the Mayflower. See where they first landed, hear how they organized their system of government, and revisit the complicated dynamic between those newcomers and the Wampanoag tribe. Drive out to Cape Cod, where colonial history collides with the present. Cruise past historic villages and continue along the coastline to explore towns like Gloucester and trace their seafaring history. Ride along a rocky shore dotted by beaches, and catch some sun and surf. Head to Lexington and Concord and follow the route of a battle between an American militia and the British army. Find out how the Americans turned the tide, and what it meant in the fight for independence. Finally, retreat to Martha’s Vineyard. Visit cute towns and learn some surprising history.

Add dates

Things to do in
Gloucester, Massachusetts

Gloucester, Massachusetts

Go beyond Gloucester, Massachusetts

Explore all

Frequently asked questions about Gloucester, Massachusetts

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

What are the best inexpensive tours in Gloucester, Massachusetts?

Other Sightseeing Options in Gloucester, Massachusetts

Want to discover all there is to do in Gloucester, Massachusetts? Click here for a full list.

What people are saying about Gloucester, Massachusetts

Overall rating

4.3 / 5

based on 6 reviews

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.