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10 Fun Fall Activities You’ll Love on Cape Ann

Fun Fall Activities You’ll Love on Cape Ann | Find Fall Activities Near Me
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Things to Do on Cape Ann

Find Fun Fall Activities Across Cape Ann

Cape Ann is a popular and well-known summer destination, but fall is one of our best-kept secrets. After the summer crowds have gone, crisp weather and vibrant foliage appear, along with a slew of fantastic fall activities and events. 

1. Fall Foliage & Leaf Peeping Day Trips 

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 places where the fall colors take over the green spaces in a spectacular fashion. Cape Ann is also an excellent home base for day trips to other parts of Massachusetts, New Hampshire, or Maine.

Fall colors starting up at Thomson Street Reservation
Fall colors just starting up at Thomson Street Reservation.


2. Plein Air Painting

"En plein air" is French for "in the open air," which is how plein air artists work, heading outdoors to paint landscapes or scenes they can observe. Cape Ann is home to the Cape Ann Plein Air Competition & Festival, which takes place in October and is a week-long celebration of plein air art and artists. Participating artists from around the country compete for prizes, painting in scenic locations throughout Cape Ann (Gloucester, Rockport, Essex and Manchester-by-the-Sea). Cape Ann has long been a haven for artists, who flock here for the special quality of natural light and the rugged beauty of the coast.

The Cape Ann Artisans Fall Studio Tour also takes place over the Columbus Day weekend (the first weekend of the Plein Air Festival) and allows you to visit twenty unique art studios across Gloucester and Rockport during the self-guided Open Studios Tour.

You can find plein air painters around Cape Ann in every season.
You can find plein air painters around Cape Ann in every season.


3. Whale Watching, Fishing and Schooner Sails

Adventure on the high seas doesn't stop after Labor Day. Whale watch excursions (7 Seas Whale WatchCpt. Bill & SonsCape Ann Whale Watch) run into October and the ever-popular schooners (Schooner Thomas E. LannonSchooner ArdelleSchooner Adventure) offer public sails through the end of September. Most fishing charter outfits also run well into the fall.

4. Learn About Local History & Heritage

The Cape Ann Museum offers a fascinating walk through Cape Ann's past and present with a mix of permanent and special exhibits. Learn about Gloucester's fishing industry, Rockport's granite quarries, as well as the art and artists inspired by the Cape Ann landscape.

Maritime Gloucester makes learning about marine science, maritime heritage and environmental stewardship fun with interactive exhibits and living creatures in the Sea Pocket Aquarium.

At one point in time the shipyards of Essex built more two-masted wooden fishing schooners than any other place in the world. The Essex Shipbuilding Museum tells that story through artifacts and tools, photos, documents, videos, and hands-on activities. 

Visiting the Cape Ann Museum is a fun fall activity for the whole family.
Visiting the Cape Ann Museum is a fun fall activity for the whole family.


5. Bird Watching

In autumn, birds who migrate northward into Canada return to Cape Ann and make their winter homes. Buffleheads, Harlequin Ducks, Northern Gannets and King Eider are just some of the species seen in the area. For information on some of the most popular birding hot spots on Cape Ann, check out our blog post on off-season bird watching.

6. Live Theatre, Music and Film

Gloucester Stage offers a world-class theatre experience, presenting a mix of new plays and beloved classics in an intimate 190-seat setting. The regular performance season runs through October.

Rockport Music presents a wide variety of concerts and events at the visually stunning Shalin Liu Performance Center. Classical music, jazz, pop and world music concerts fill the calendar year-round, in addition to a film series and HD broadcasts from the Metropolitan Opera and England’s National Theatre.

The Cape Ann Cinema is a small community movie house that describes itself as "A 100-seat living-room-style cinema in the heart of historic Downtown Gloucester." They show an eclectic selection of independent movies, foreign films and mainstream Hollywood flicks.

7. Local Fall Festivals Across Cape Ann

Trails and Sails is a massive cultural event that takes place in towns across the North Shore. Historical homes, museums, parks and other Essex Heritage locations offer free tours and activities that celebrate the history and heritage of Essex County.

Rockport's HarvestFest celebrates the bounty of the season with local food, craft beverages, cooking demos, a farm expo and live music. The Scarecrow Stroll contest positions  artistic and creative scarecrows throughout the downtown area; vote for your favorite and the winner will take home bragging rights and a cash prize. 

In October, Hammond Castle is transformed into a haunted castle for Halloween, complete with scary sounds, monsters hiding in dark corners and ghoulish displays. 

Essex ClamFest hosts a variety of activities including arts and crafts, food and live entertainment in Memorial Park in Essex. The highlight of the day is the Clam Chowder Tasting, featuring local restaurants competing to determine who serves the best clam chowder on Cape Ann.  

8. Eat Seasonal Local Foods

The Cape Ann Farmers Market runs through mid-October on Thursdays at Stage Fort Park and the Rockport Farmers Market is on Saturdays at Harvey Park, also through mid-October. Marshall's Farm Stand in West Gloucester sells fresh, local produce, locally made desserts, breads, local butchery meats, cheeses and other dairy products and is open through the end of October.

9. Apple Picking

Russell Orchards in nearby Ipswich offers apple picking (with many apple varieties to choose from) but if you don't want to pick your own, you can browse the farm store for a delectable assortment of apple cider donuts, fresh produce, and locally sourced specialty items.

10. Enjoy Locally-Brewed or Distilled Craft Beverages

Feeling thirsty? From beer and wine to mead and rum, locally made craft beverages are to be found all over the North Shore. The North of Boston CVB’s “Sips, Suds & Spirits Trail” map takes you on a self-guided tour of local brewers, distillers and winemakers.

Try one of the North Shore's locally made craft beverages this fall.
Try one of the North Shore's locally made craft beverages this fall.


Where to Stay for Your Cape Ann Fall Break

Atlantic Vacation Homes offers a wide variety of vacation rental homes across Cape Ann that would be perfect for your North Shore getaway. And after Labor Day, you'll enjoy lower autumn rates! To book your accommodations, simply view available vacation rentals and enter your desired dates to get a quote. You can also call toll-free at (855) 853-9143 to speak with a Guest Experience Specialist.


Atlantic Vacation Homes Atlantic Vacation Homes is the premier vacation home rental & real estate company on Boston's North Shore, with over 30 years of creating dream vacations for our guests. Situated a little more than a half-hour’s drive from downtown Boston, the North Shore is the ideal spot for an east coast vacation. We specialize in coastal vacation rentals for families, large groups, and anyone else who wants a beach vacation in Massachusetts.