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Autumn on Cape Ann

October 1, 2019

When people think about Cape Ann they envision beaches, scenic ocean views, and small coastal communities to visit during the warm summer months. While summer may be our peak season up here on the “other Cape,” autumn is just as nice a time to visit.

Leaf Peeping 

The ride to the North Shore along Route 128 or scenic 127 will begin your adventure to the quiet seaside communities that enjoy the fall almost as much as the summer. Along your route, you will experience some of the most fantastic leaf displays. The colors in this region are sharp and combine with the salty smell of the ocean to make for a wonderful day outing. 

Enjoy the leaves in many locations on the North Shore during your visit. There are many opportunities for leaf-peeping around Cape Ann. Ravenswood Park, Thomson Street Reservation, Dogtown Commons, and Halibut Point State Park are just a few of the places where the fall colors take over the green spaces in a spectacular fashion.

Get Out on the Sea

Whale watching, schooner trips, and water tours of the local lighthouses don’t stop just because the calendar has turned to the fall months. In fact, many people enjoy outdoor activities more during this season because the weather is a little cooler and since the kids are back in school, there are fewer tourists. Whale watch excursions (7 Seas Whale Watch, Cpt. Bill & Sons, Cape Ann Whale Watch) run into October and the ever-popular schooners Schooner Thomas E. Lannon, Schooner Ardelle, and Schooner Adventure offer public sails through the fall. Most fishing charter outfits run well into the autumn as well.

Celebrate with Festivals 

The North Shore of Massachusetts is famous for its festivals and celebrations during the fall season. One of the largest fairs in our region is the Topsfield Fair in Topsfield, Massachusetts from October 4th to 14th this year. Enjoy animals, food, performances, rides, and more as you explore the area with your family. 

Rockport hosts the Rockport Harvestfest which will be held on October 19th this year. The annual Rockport Harvestfest features food and entertainment under big tents on one of Rockport’s historic working wharves, and celebrates the best of local food with a farmer’s market, local meats, seafood, produce, craft beer, wine, local sodas and more. Harvestfest showcases live music, cooking demos, shopping specials, and family activities.

Experience Art 

If you love art, you may like to visit the area to watch some of the world’s most renowned artists compete in the fourth annual Cape Ann Plein Air (CAPA) outdoor painting competition and festival, which takes place in the Cape Ann communities of Essex, Gloucester, Manchester-by-the-Sea, and Rockport, will run from Sunday, October 6 through Monday, October 14. CAPA 2019 provides local, national and internationally recognized artists the opportunity to compete in the premier New England Plein Air Festival and winner of the BONS 2018 Editor’s Choice for Best Arts Festival, located in the birthplace of American Plein Air Painting, Cape Ann. 

Cape Ann communities are vibrant and active all the way through the fall. If you are staying at the Pleasant Street Inn, ask our staff about activities that you might be interested in and we can help plan your activities. We would love to help!