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A few of the many things to dowhile on your visit to Cape Ann.

Shoppers on busy Bearskin Neck, Rockport, MA
NOTE: This information is gathered from various sources and is subject to change without notice. While every effort is made to ensure accuracy there are no guarantees. This page is updated throughout the year.

May Events 

  •  Saturday, May 18 - Essex River Race, Essex. The Essex River Race is open to all seaworthy human-powered rowing and paddle boats. Participants’ crafts usually include Banks dories, fixed seat singles, doubles, multi-oars with cox, multi-oars without cox, and sliding seat singles & doubles..
  •  Saturday, May 18 - Motif No.1 Day, Rockport. Galleries and restaurants celebrate the season. Enjoy hot chowder and draw Motif No. 1 and be an artist for the day.
  •  May (Day TBA) - Artist’s Plein Air Day at Cogswell’s Grant, Essex. 9:00 am. to 4:00 pm. Artists and painters are invited to Cogswell’s Grant for a day of plein-air painting. Join fellow artists from all over the North Shore to paint beautiful vistas including the Essex River and the Great Marsh, farm fields and landscapes, and our eighteenth century historic house and barns. Free beverages and snacks will be available during the day, and artists can take a free tour of the museum and its important collection of American folk art.
  • Monday, May 27 - Memorial Day Parades, Cape Ann.

June Events 

  •  Saturday, June 1 and Sunday, June 2 - Cape Ann Artisans Studio Tour. The self-guided tour presents a rare opportunity to meet a number of professional artists, see their work and demonstrations in their studios.
  •  Friday, June 7 to Sunday, June 9 - Art in the Barn. Annual art exhibit and sale at the Cox Reservation Studio Barn, Essex, to benefit the Essex County Greenbelt Association featuring fine art, pottery, indoor and outdoor sculpture, fine crafts, and jewelry.
  •  Tuesday, June 14 to Thursday, July 14 (tenative) - Rockport Chamber Music Festival. A variety of outstanding musical performances by world-renowned musicians for people of all ages at the Shalin Liu Performance Center, Rockport.
  •  June (Day TBA) - International Dory Races. Gloucester vs. Lunenburg, Nova Scotia at Jodrey State Fish Pier, Gloucester.
  •  June (Day TBA) - Essex River Day. Those who have a boat offer a neighborly boat ride to those in town who may not have a boat and don’t have ready access to appreciating the wonders of the Essex River. This simple thought has grown into a full day of events culminating that evening with a softball game, a cook out, music and a bonfire at Memorial Park.
  •  Wednesday, June 26 to Sunday, June 30 - St Peter’s Fiesta, Gloucester. A five day festival organized by the Italian American community honoring the patron saint of the fisherman St. Peter.

July Events 

  •  Tuesday, July 3 and Wednesday, July 4 - Independence Day Parades. The people of Cape Ann celebrate Independence Day with fireworks, parades, bonfires, concerts, and more.
  •  July (Day TBA) - Downtown Gloucester Block Party. All are invited to the free downtown block party on Main Street, Gloucester! Get ready to dance and party.
  •  Saturday, July 13 - Blackburn Challenge, Gloucester. Sponsored by the Cape Ann Rowing Club, this is a 20 plus mile open water circumnavigation of Cape Ann. Open to all seaworthy oar or paddle powered craft..

August Events 

  •  Monday, August 5 to Wednesday, August 7 - Sidewalk Days, Gloucester. Main Street closes to traffic for three days with merchandise, arts and crafts, food and entertainment each day.
  •  August (Day TBA) - Manchester Arts Festival, Manchester by the Sea. Featuring fine art, sculpture, textiles, pottery, jewelry, apparel & accessories, garden ornaments, photography, paintings, and more.
  •  August (Day TBA) - Celebrate the Clean Harbor Swim. In 1979, four Cape Ann residents swam across Gloucester Harbor in protest of its polluted status. It metamorphosed into an annual Audubon Society-sponsored event to help raise funds for cleaning the harbor, hence named “Swim for a Clean Harbor”. In 1993 the harbor was deemed clean by the Audubon Society. Local resident Richie Martin stepped in to keep the event, Niles Beach, Gloucester, running and the 1.2 mile deep water swim, now known as “Celebrate the Clean Harbor Swim” has become a summer favorite for swimmers from all over.
  •  August (Day TBA) - Downtown Gloucester Block Party. All are invited to the free downtown block party on Main Street, Gloucester! Get ready to dance and party.
  •  Saturday, August 10 - Gloucester Blues Festival. World-class blues will reverberate through beautiful Stage Fort Park with some of the nation’s finest performers playing from the Gloucester Blues stage. Located right on the waterfront on beautiful Cressey’s beach, the event will have a beer garden and outstanding food and craft vendors..
  •  Saturday, August 17 and Sunday, August 18 - Gloucester Waterfront Festival. Spend a summer day in beautiful Stage Fort Park with the exciting displays of over 150 artisans and craftspeople, live music, plus delicious ethnic foods.
  • August (Day TBA) - Downtown Gloucester Block Party. All are invited to the free downtown block party on Main Street, Gloucester! Get ready to dance and party.
  •  Friday, August 30 to Monday, September 2 - Gloucester Schooner Festival. The Mayor's Race for 100 foot schooners, races for other classes, parade of sail, deck tours, public sails, lighted boat parade, fireworks, and other maritime activities.

September Events 

  •  Sunday, September 1 to Monday, September 2 - Gloucester Schooner Festival. Continuation of The Mayor's Race for 100 foot schooners, races for other classes, parade of sail, deck tours, public sails, lighted boat parade, fireworks, and other maritime activities.
  •  September (Day TBA) - Herrmann’s Royal Lipizzan Stallions of Austria, Cogswell’s Grant, Essex. 2:00 pm to 3:30 pm. The Herrmann family, breeders and trainers of the famed Lipizzan horse for over three hundred years, demonstrate the highest levels of horsemanship in three shows. The stallions of the Herrmann line are among the last horses capable of executing the “Airs Above the Ground” maneuvers. These dramatic leaps and plunges were developed as aggressive battle maneuvers in the sixteenth century, and are now among the most beautiful displays of equine grace and strength.
  •  September (Day TBA) - Trails & Sails: Two Weekends of Walks & Water Essex County. Go Hike! Go Bike! Go Paddle! Go Sail! Go experience the natural beauty, cultural resources and American heritage found in the Essex National Heritage Area.
  •  September (Day TBA) - Coastal Farming Walking Tours. Walk through the fields and down to the marsh, learn about the rich history of the families that lived and farmed at Cogswell’s Grant, Essex, and how coastal farming has evolved over nearly four centuries.

October Events 

  •  October (Day TBA) - Annual Annisquam Arts & Crafts Show. Annisquam Village Hall 10:00 am to 5:00 pm. The show features works of more than 40 crafters and artists from Cape Ann featuring handcrafted jewelry, ceramics, pottery, children’s toys, silk scarves, designer jackets and accessories, and as well as a wide selection of art work by local artists in the Tent Gallery.
  •  Saturday, October 12, Sunday, October 13 and Monday, October 14 - Cape Ann Artisans Studio Tour. Meet the artists and see their work in the places where it is created.
  •  October (Day TBA) - Cape Ann Plein Air Competition and Festival. For nearly two centuries, Cape Ann has been a destination for some of the finest painters who paint “en plein air”. Throughout its four picturesque seaside communities, will be host to a week-long plein air painting celebration in October when the famous Cape Ann light shines at its very best. The communities will see 40 of the finest artists in the nation and work produced will be sold at the Grand Awards Gala at North Shore Arts Association .
  •  October (Day TBA) - Gran Prix of Gloucester. Known nationally as “the New England Nationals”, the Gran Prix of Gloucester unfolds at one of the most beautiful race venues in the country: the wind-swept oceanside Stage Fort Park on beautiful Cape Ann. Two days of international cyclocross races where competitors from all over the US, Canada and Europe converge to race on the most beautiful race course in North America.
  •  October (Day TBA) - Rockport Harvest Festival. A family-oriented day with an autumn theme is designed to entertain and delight residents and visitors alike.
  •  October (Day TBA) - Essex ClamFest. The highlight of the Annual Essex ClamFest, Memorial Park, Essex is the Clam Chowder Tasting Festival, a competition for area restaurants to determine who serves the best chowder on Cape Ann. In addition to the competition, there is an interesting variety of activities , including an arts and crafts area and entertainment throughout the afternoon.