Signature Events

2022 Cape Ann Chamber Signature Events

Gloucester Block Parties

July 16, 2022 | August 3, 2022 | September 2, 2022

Two popular summer events that celebrate all that downtown Gloucester has to offer. Guests enjoy live music, street performers, family friendly activities, contests, games, and more!

Gloucester Waterfront Festival

August 20 &. 21, 2022

More than 175 juried artists and craftsmen from throughout the United States will be coming to Gloucester for this festival, now in its 40th year. Live music, unique creations and delicious food will highlight the two-day event.

$25,000 Game

October 27, 2022

Every October, the Chamber hosts the premier giveaway night on Cape Ann where $25,000 is given away, including a grand prize of $10,000!

Cape Ann Plein Air

October 2 – 9, 2022

Stroll through artist galleries and studios nestled on the

Atlantic. Grab lunch on the water overlooking a working fishing harbor.

Experience arts and culture at one of the world-class museums, theater, or

heritage center. Venues offer a calendar of special events and daytime

galleries perfect for a casual visit or an overnight stay. Many paintings will

be available for sale during the full duration of the competition and festival.

Selected works will be shown and available for sale during the Gala Reception

and Awards Presentation, at the conclusion of the competition. This is your

chance to purchase works by some of the top names in contemporary painting.

Essex ClamFest

October 22, 2022

This event has grown every year to become one of the best attended Festivals in the region. This annual event has everything this small town is known for, including: arts and crafts, K-9 demonstrations, lots of food vendors and of course, the ever popular Clam Chowder Competition. Nearly 1,000 people attend to taste the best of the best, each voting for their favorite in the People’s Choice Award, while nine esteemed judges helped to select the winner of the Judge’s Award. Proceeds from this event go in part to supporting the local Essex Merchants, Lions Club and the community.

Love Cape Ann Fundraising Auction

September 29, 2022

The Chamber’s biggest fundraiser! With over 200 attendees, the auction is one of the largest on the North Shore. This is a wonderful way to support the organization and help build stronger Cape Ann Businesses and the community as a whole.

Celebrating the Holidays on Cape Ann

December 1, 2022 – January 1, 2023

Celebrations that last the full month in each of the four communities and include several events.

Greater Cape Ann Small Business Week

June 6 – 13, 2022

Every year since 1981 the Cape Ann Chamber of Commerce has set aside a week to honor the achievements of Cape Ann’s small business entrepreneurs and their employees, and their

contributions to the economic vitality and community life of Cape Ann.


This year the Chamber has designated September 19 through September 24 as Cape Ann Small Business Week 2021. Small businesspersons of the year for each Cape Ann community will

be selected by committees comprised of past recipients of this annual recognition. 

Nominations are welcome and encouraged. Nominees for each community should be associated with established businesses that have made significant contributions to the economic vitality and community life of Cape Ann.

Annual Celebration

January 21, 2022

The Chamber’s way to kick-off the new year, held at an upscale venue and attended by 200+ senior business leaders and guests including local, city and state officials. This is a fantastic opportunity to promote your business in front of many area business owners, senior business leaders, and elected officials.

Irish Sweepstakes

March 17, 2022

This is one of the most exciting and fun filled events on Cape Ann as a total of $20,000 cash is given away- including one Grand Prize of $10,000! The Irish Sweepstakes also features live Irish music, a 50/50 raffle, a traditional Irish dinner and much more!

Cape Ann Chamber Education & Scholarship Golf Tournament

May 23, 2022

Played at the Bass Rocks Golf Club and typically attended by 100 Chamber members and guests. These are some of our most highly sought after sponsorship opportunities. Some of the proceeds from this event go toward four college scholarships – a great way to help our local youth become successful business people!

Festival by the Sea

August 6, 2022

Enjoy the summer in classic New England style in one of the North Shore’s most beautiful and

prosperous towns – Manchester-by-the-Sea. This all-day extravaganza celebrates locally grown art, music and food. The festival highlights the idyllic beauty of Cape Ann and the incredible talent for which the area has become synonymous. This is the most heavily attended of all Chamber events and as such offers incredible opportunity for exposure and to promote your business