Scenic Cape Ann Self-Guided Driving Tour in Gloucester & Rockport

Cruise along the road less traveled on Cape Ann, where adorable villages, stunning beaches, and history dating back hundreds of years come together. On this flexible, app-based tour, you can move at your own pace and stop for photos wherever you’d like!

The tour begins just outside Gloucester, with gorgeous views of the harbor. Here, you’ll find the enormous Tablet Rock, which opens a window to the year 1623, when Pilgrims first landed on these shores. Hear all about their struggles to survive in this harsh new land.

Next, head into Gloucester and dive into the town’s uniquely New England culture. Learn about the importance of fishing to this community, the dangers of that high-stakes profession, and the tragic story behind the Perfect Storm, which still reverberates through this town to this day.

Then, visit Gloucester’s harbor to see why locals simply can’t live anywhere but here. Meander along the gorgeous harborwalk, breathe in the salty sea air, and maybe even spot a few whales!

After that, cruise along with the cape’s artsy southern point and discover the artist colony of Rocky Neck and the spectacular Niles Beach, perfect for catching some sun. Admire the huge, 56-room mansion of Beauport, then snap some iconic Massachusetts photographs of the Eastern Point Lighthouse.

Drive-up the eastern coastline next on your Cape Ann Harbor tour, past plenty of spotless beaches, including the unbelievably picturesque Pebble Beach, which feels like it was practically made for Instagrammable moments! Listen to the tale of Thacher Island just beyond the shore and the shipwreck which put it on the map.

Then, head through Rockport and hear the wild story of Hatchet Hannah and her crusade against alcohol. After picking up on the local history, you’ll get the chance to see the most painted building in the entire world. No, really!

Venture north to the most remote part of the cape, and listen along the way to the harrowing events of the infamous Blizzard of 1978 and another equally terrible storm over a century earlier. Then, stretch your legs in the beautiful Halibut Point State Park, which offers breathtaking ocean views you can’t find just anywhere.

Finally, angle back toward Gloucester, but not without getting the inside scoop on the so-called Witch House and the devastating shipwrecks that have occurred along this cape over the years. This comprehensive, self-guided driving tour will show you everything there is to see on the Cape Ann Harbor tour and fill you in on all the stories you need to hear while you’re at it!

Starting Point Address: Glouchester Visitor Center at Stage Fort Park, 24 Hough Ave, Gloucester, MA 01930