10 Fun Fall Activities You’ll Love on Cape Ann

Gloucester · Rockport · Essex · Manchester-by-the-Sea
Cape Ann,kept by the people who live here
Sixty-one homes across Boston’s North Shore, looked after by the family that has welcomed guests here since 1985. Book direct and skip the platform fees.
Atlantic Vacation Homes is a family-owned, full-service vacation rental and real estate company rooted in the four coastal towns of Cape Ann, a little more than half an hour north of Boston.
Hear first when this host opens direct rates or adds a new place.
The homes
Waterfront antiques, beach houses a short walk from the sand, cottages in Rockport’s lanes. Three are open to book on this site today; the full collection is on atlanticvacationhomes.com.
Book direct
The booking sites add a traveler fee of up to 15% to the same home you can book here. Book with us and that fee stays in your pocket, you get our Best Price Guarantee, and the person who answers the phone knows how many steps it is from the driveway to the front door.
Atlantic Vacation Homes
Cape Ann
Photos courtesy of Google.

Vacation Nation
A la carte packages and rentals, arranged before you arrive. Ask our Guest Experience team when you book, or add them later.
From Jonathan
I was born and raised in Gloucester and grew up in this business; my mother Carole built it from the ground up. I came home after college and a career in sports management to carry what she built into its next chapter, and I have worked every role here, from reservations to maintenance.
What has not changed is the promise: a home that is clean, fully equipped and exactly as described, a local team you can reach, and the best price when you book with us directly. Call us at (978) 290-4331 or write to info@atlanticvacationhomes.com with any question at all. We would love to show you our Cape Ann.
Jonathan Fonvielle
President, Atlantic Vacation Homes
Pack Lighter
Through our Pack Lighter program, guests leave unopened food behind and we deliver it to The Open Door food pantry in Gloucester. Our staff volunteer with the Rotary Club of Gloucester, Action, Inc., the Cape Ann Chamber of Commerce and Discover Gloucester; retired linens go to Cape Ann Animal Aid and the Beverly High School culinary program; and we partner with Triangle, Inc. to employ young people and adults with disabilities.
Affiliations
In motion
The river at River Watch, the beach from Over By Good Harbor, Rockport harbour.
Getting here
Cape Ann is a little under an hour from Boston and Logan Airport by car, up Route 128 to the A. Piatt Andrew Bridge. The MBTA commuter rail runs from North Station to Manchester, Gloucester and Rockport, and the CATA buses and the Rockport shuttle cover the towns in summer. Head north along the coast for Newburyport and Plum Island; south for Beverly and Salem.


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 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.

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 Watch, Cpt. Bill & Sons, Cape Ann Whale Watch) run into October and the ever-popular schooners (Schooner Thomas E. Lannon, Schooner Ardelle, Schooner 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.
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.
Blackburn Brewfest sets up next to the beach at historic Stage Fort Park in Gloucester in late September, offering hundreds of beers, ciders, and meads brewed by close to 30 Massachusetts breweries.
In October, Hammond Castle adds fun “spooky season” events alongside their regular tours.
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
Most area farmer’s markets run through the summer into mid-October and offer a variety of locally-grown and sourced foods. Rockport Farmers Market is on Saturdays at Harvey Park.
Gloucester’s Backyard Growcery operates on Wednesdays at Burnham Field.
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 Orchardsin 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.
Marini Farm in Ipswich delights children of all ages with a 7-Acre Corn Maze each autumn. Adults over the age of 21 can go in the evening for their “Brew Your Way Through” beer tastings inside the corn maze!
10. Enjoy Locally-Brewed Craft Beverages
Feeling thirsty? Crisp fall days and locally crafted drinks are a pretty perfect pairing. The North Shore is home to a robust craft beverage scene, so check out Northshore Magazine’s roundup of local breweries. Whether you’re in the mood for beer, wine, cider, or mead, we’ve got you covered!
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 us at (978) 290-4331 to speak with a Guest Experience Specialist.