Gloucester
America's oldest seaport. Home to whale watching, fishing, and beautiful beaches.
Explore Our Towns
Rockport
A quaint art colony famous for Motif #1, Bearskin Neck, and rocky shores.
Essex
The antique capital of America and home to the best fried clams in the world.
Manchester-by-the-Sea
Scenic harbors and the famous Singing Beach. A perfect quiet getaway.
Things to do
Looking for lots of miniature golf courses, fast food restaurants, and crowded tourist traps? You won't find any on Cape Ann. What you will find on our Cape is whale watching, sailing, fishing charters, beaches, kayaking, museums, and countless other fun things to do on the water. You can also enjoy hiking/biking through old forests or along a rugged shoreline, explore historic stone quarries, or get lost in hundreds of acres of mountain biking/hiking trails. Don't miss the events list below.
The Arts
Cape Ann boasts both a rich history and wide variety of arts. A long list of well known painters, sculptors and writers have long been inspired by our shores. Two of the nation's oldest artist colonies, Rocky Neck Art Colony in Gloucester and Bearskin Neck in Rockport, serve as a mecca for both artists and art lovers worldwide. Several outstanding art associations, such as the North Shore Art Association, harness the creative energy that surrounds Cape Ann. And there is no other place in New England that hosts such a rich variety of holistic health practitioners as Cape Ann. Our Cape also boasts a number of outstanding museums specializing in fine art, historic collections, seafaring, and natural history. We are also proud to be home to the Gloucester Stage Company, Rockport Chamber Music and Theatre in the Pines and the Rockport Chamber Music Festival.
Nov
6–8
North Shore Arts Holiday Market
The gallery's last open weekend of 2026 doubles as a holiday market, held in partnership with Cape Ann Artisans. Browse wearable art and works of all sizes for holiday gifts, with hot cider and coffee on hand. All are welcome.
Nov
7
From the Deep: A Downtown Gloucester Arts Party
A fall day of art and culture around downtown Gloucester, with live art making and demonstrations, music, a children's sketching contest, a walking tour of the "Imagining Gloucester's Future" window murals, and an art giveaway. Organizers are still adding artists and activities, so check the schedule before you go.
Dec
4
Holiday Stroll — Manchester-by-the-Sea
Manchester's annual Holiday Stroll and business open house fills downtown with refreshments at shops around town. Pick up a Holiday Stroll stamp card and collect stamps at the participating shops as you go.
Dec
5
Christmas in Rockport — Santa's Arrival & Tree Lighting
An old-fashioned Rockport Christmas: Santa arrives by boat at T-Wharf in the afternoon, followed by photos with Santa, holiday carolers, and a tree-lighting program at Dock Square with the Dock Square Singers. It kicks off a holiday season in town that runs from Small Business Saturday (November 28) through New Year's Eve.
Dec
6
Friendship Tree Lighting — Manchester-by-the-Sea
A full day of holiday events in Manchester: breakfast and photos with Santa at the American Legion (9 AM–noon, $12 per person, kids under 5 eat free), a community carol sing at First Parish Church at 2:30 PM, cocoa on the green, and the Friendship Tree lighting at 3:30 PM. Produced by the Manchester Woman's Club, with music from local students and candy canes from Mrs. Claus.
Dec
12
Lobster Trap Tree Lighting
Gloucester's one-of-a-kind holiday tradition: a towering tree built from stacked lobster traps and decorated with painted buoys and lights, lit on the harborfront. Past celebrations have included hot cocoa and holiday crafts at nearby Maritime Gloucester.
Dec
12
Middle Street Walking Tour
A Cape Ann Museum docent leads a roughly 45-minute walk along historic Middle Street, exploring the people, places, and events that shaped the neighborhood. The museum is free and open to the public all day, with holiday ornament-making, exhibitions, and the Museum Store.
Dec
31
Rockport New Year's Eve
A small-seacoast-town take on a First Night celebration: music of many genres, jugglers, puppeteers, storytellers, and dancers at downtown venues, a parade through the streets, and the midnight ball drop in Dock Square. Admission is by button, sold in advance in Rockport and Gloucester or at event headquarters on the night. Check the website for the 2026 schedule.
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Why Visit Cape Ann?
Unlike the crowded Cape Cod, Cape Ann offers a rugged, authentic New England experience. Located just 30 miles north of Boston, this region is a haven for artists, history buffs, and ocean lovers. Whether you are looking for the best whale watching in New England or the freshest lobster rolls, Cape Ann delivers year-round.