2023 Cape Ann Chamber Signature Events

2nd Annual WellFest: A Greater Cape Ann Wellness Fair

Saturday, May 20, 2023

Join the Greater Cape Ann Chamber’s Health & Wellness Committee for the 2nd Annual WellFest: A Greater Cape Ann Community Wellness Fair. This year, we are moving to Harvey Park in Rockport!

This event will showcase the Cape Ann region’s broad range of health and wellness services. This event will provide something for people of all ages!

Learn More and Request Vendor Information

34th Annual Cape Ann Chamber Education & Scholarship Golf Tournament

Monday, May 22, 2023

Played at the Bass Rocks Golf Club and typically attended by over 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! Learn more about sponsoring and / or playing.

Small Business Week Winners

Greater Cape Ann Small Business Weeks

June 5 – 16, 2023

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.

Main Street Block Party

Gloucester Block Parties

July 15, 2023 | August 12, 2023 | September 1, 2023

Three 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!

Follow Main Street Block Parties on Facebook

12th Annual Festival by the Sea

Saturday, August 5, 2023

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.

View Listing of 2022 Artisans, Food Vendors, Non-profits & Brewery

Follow Festival by the Sea on Facebook

Gloucester Waterfront Festival

Saturday, August 19 & Sunday, August 20, 2023

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. Gloucester Waterfront

2nd Annual Blackburn Brew Fest

Saturday, September 16, 2023

The Blackburn Brew Fest debuted in 2022 and became an instant hit. Join us and over 30 breweries for an afternoon of craft beer tastings, live music, food trucks and games at Stage Fort Park in Gloucester.

Presented by the Greater Cape Ann Chamber of Commerce and NEXTGEN Young Professionals to celebrate the Chamber’s 100th Anniversary year.

Visit Blackburn Brew Fest to learn more.

Love Greater Cape Ann Fundraising Auction

36th Love Cape Ann Fundraising Auction

Thursday, September 28, 2023

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.

Follow Cape Ann Community Foundation on Facebook

Cape Ann Plein Air

October 1 – 8, 2023

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.

Follow Cape Ann Plein Air on Facebook

39th Annual Essex ClamFest

October 21, 2023

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. Learn more.

$25,000 Game

October 26, 2023

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!

Celebrating the Holidays on Cape Ann

November 30 – January 1, 2023

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

Follow Christmas in Rockport on Facebook

Follow Christmas by the Sea on Facebook

2023 Completed Events

101st Annual Celebration

Friday, January 27, 2023 at the Beauport Hotel

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.

Download Annual Celebration Sponsorship Form

24th Annual Irish Sweepstakes

Thursday, March 16, 2023

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!

Download 2023 Irish Sweepstakes Sponsorship Form

Winter Birding

Annual Winter Birding Boat Trip

Saturday, March 25, 2023

Cape Ann is known worldwide for its exciting concentrations of winter seabirds. Thousands of birders visit the rugged coast of Cape Ann and scan the adjacent waters hoping to spot some of the unusual and highly sought-after seabirds that spend the winter months just offshore. The best way to get to see these birds and experience them up close is to visit them in their natural habitat- on the ocean!

Learn More & Register