Cape Ann Self-Guided Driving Tour in Gloucester and Rockport

Our Cape Ann excursion begins at the Gloucester Visitor Information Center. We'll get our view breathtaking views of the waterfront from this point. Note: This 24 mile-long tour covers the essentials of Cape Ann in 1-2 hours.

Instead of setting off on our drive right away, we'll first check out the most striking feature of the scenery: the massive Tablet Rock. In 1907, the plaque the rock was unveiled to Commemorate the first settlers in this area.

We can also choose to walk around this area before our driving, admiring the amazing views of the park, the ocean, and the city.

Our drive along Cape Ann's scenic harbor begins once we cross the canal. First, we'll admire Cape Ann's most famous momument: the Fisherman's Memorial. As we continue, we'll learn about the significance of fishing in Cape Ann's past — and the famous movie about it, "The Perfect Storm".

Here we can choose to pause again to explore Cape Ann's Harborwalk. Along the path are 41 granite slabs containing pieces of the town’s long, odd, sometimes sad history. These “story moments,” as they are called, were put together by teams of volunteers eager to show the world what Gloucester is made of. Taken together, they form a mosaic of this strange, beautiful place.

Cape Ann and Glouchester’s whale watching industry guarantees whale sightings with every voyage. Their boats often take passengers to a marine wildlife preserve that’s been called one of the top five whale-watching destinations in the entire world!

As we drive along scenic Cape Ann's waterfront, we'll discover beaches both big and small. We can choose to stop at one, some, or all, as we learn more about what's unique about each one.

Beauport, also known as Sleeper–McCann House, Little Beauport, or Henry Davis Sleeper House, is a beautiful historic home tucked away on the Cape Ann waterfront. As we drive, we'll dive back into Cape Ann's history.

During the early 1800s, maritime trade in Gloucester was booming. Ships traveling between these ports and China or India were turning enormous profits, and captains started to become especially anxious at the prospect of losing their extremely valuable cargo in a shipwreck. Enter: lighthouses!

Thacher Island is a small island off Cape Ann on the Massachusetts coast in the United States. It is a part of the Town of Rockport. It was a place where some naval confrontations, both minor and major, took place, which helped secure a victory for the colonists.

Annisquam Harbor Light Station is a historic lighthouse on Wigwam Point. As we approach, we'll learn more about shipwrecks, shipping, fishing, and maritime trade.

Our brings us to "the most painted building in America"!

This land was once home to a large number of bears, but don’t worry! They’re long gone now. According to legend, one such bear was caught by the tide and killed in 1700, which is how this place got its name.

Our scenic drive along Cape Ann now leaves Gloucester and brings us into Rockport. We'll learn more about Rockport and the region as we drive.

Granite Pier is one of the Rockport’s oldest piers. As you might have guessed, this used to be where ships would be loaded with granite for transport. As we explore the pier and nearby beaches, we'll get a better understanding of the Cape Ann of days past, and that of the present. Our drive then continues along Halibut Point and Harvey Reservation.

Halibut Point State Park and Halibut Point Reservation are adjacent parcels of conserved, oceanside land located on Cape Ann in the town of Rockport, Massachusetts.

Front Beach is a beautiful sandy beach on Sandy Bay in Rockport. From warm summer days to bright winter mornings, this beach is enjoyed by visitors

Located on Washington Street in the northern section of the City, this small, quiet beach has been enjoyed by families in Lanesville for many years. It is a great place to bring small children due to the small confines of the beach. Parking is limited and restricted to vehicles with a current City of Gloucester beach sticker.

Harvey Reservation is one of the best spots on Cape Ann to sit and watch the sunset. This small reservation offers a short trail, a granite bench, and a terrific spot for a seaside picnic.

Our scenic drive along Cape Ann has finally looped back to Stop 1! We're nearly back at the Gloucester Visitor Information Center.