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August 31, 2022

Schooner Festival | Robert Serbagi

Chamber Events

Main Street Gloucester Block Party

Friday, Sept. 2 | 6 - 10 PM

We have had two fantastic Block Parties so far this summer - help us make it three!

Join us for the last block party of the year on Friday, September 2 to kick off Schooner Festival weekend. Once again Kilted Colin will be showing you what is under his kilt, and this time, Bosoma School of Dance will have the spotlight dance session. There will be music, face painting, Mary Poppins and Captain Jack. Visit with your favorite non-profits, shop the Main Street merchants, play games, and satisfy your hunger at the five food vendors. Come down to Main Street and help us make this one of the most successful block parties!

Download Flyer

Businesswomen's Mixer

Thursday, September 8 | 5 - 7 PM

The Gloucester House

Members: $10 | Non-members: $15


The Gloucester House is hosting the next mixer presented by the Businesswomen's Committee on Thursday, September 8. Join us for an evening of networking, fun and raffles! All are welcome to join in

Please register in advance if you plan to attend.

All proceeds benefit the Carolyn M. O'Connor Scholarship Fund.


Blackburn Brew Fest

Saturday, September 17 

1 to 5 PM

Stage Fort Park, Gloucester

Experience one of the best views on Cape Ann with a cold beer in your hand this September at the First Annual Blackburn Brew Fest presented by the Chamber’s Next Gen Cape Ann Young Professionals Group. Located next to the beach on the historic Stage Fort Park, sample hundreds of beers and ciders brewed by 30 Commonwealth breweries while listening to local band Over the Bridge, playing lawn games, and dining from local food trucks.

Tickets are now on sale at

35th Annual Love Greater Cape Ann Fundraising Auction

Thursday, September 29 | 5 - 10 PM

Cruiseport Gloucester

$75 per person - Table of 10 $750

We Love Greater Cape Ann and work hard to help support our Community in many ways. Your generous bidding will help the Chamber build for the future of this special place where we live, work and play. 

Live Auction/Silent Auction

Fund the Future Paddle Raise

Heads & Tails Game

Passed Hors d'Oeuvres, Plated Dinner, Cash Bar

Limited Seating - Get Your Tickets Today


38th Annual Essex ClamFest

Saturday, October 22 

11 AM to 4 PM

Memorial Park, Essex 

(Rain Date: Sunday, October 23)

Come taste Cape Ann’s finest chowders! Although the highlight of the day is the Chowder Tasting Competition, there are a great variety of activities, including arts and crafts vendors, live entertainment and plenty of food vendors on-site! 

Sponsorships are available. Learn more about how you can help support this great event.

Vendor spaces also available. Download vendor application. 

New Member Special Advertising Section

Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings

Schooner Festival over Labor Day Weekend 

Schooner Festival starts Thursday, September 1 and concludes with the schooner race on Sunday, September 4. This capstone to the summer is steeped in history and jam-packed with events and opportunities to get up-close and personal with these beautiful ships.

Schooner Festival Schedule  | List of Participating Schooners.

Schooner Lannon

Schooner Festival Weekend

Thursday September 1: Schooner Challenge - Haul the Anchor, Set Sail, and Race our local schooners in this sunset challenge

Friday, September 2: Visiting Schooners begin to arrive, Join us for a public sail! 

Saturday, September 3: - Boat Parade of Lights & Fireworks Sail -Tickets Available

Sunday, September 4: Mayor’s Race for the Esperanto Cup – Join us for RACE DAY! Tickets available.

Buy Tickets

Schooner Adventure

Schooner Festival Weekend 

Join Schooner Adventure for the Greet the Fleet Sail, and the Heritage Day Sail during Gloucester’s famous Schooner Festival over Labor Day weekend. Spots aboard Adventure for the full day Mayor’s Race in competition for the famous Esperanto Cup on Labor Day sell out quickly every season!

Buy Tickets

Manchester 1772: Work & Life in A Small Fishing Town

Manchester Historical Museum

Time is running out to see the exhibit.

This is the state’s only exhibit on what was, for 200 years, the economic engine of Massachusetts: the catching, curing, and trading of salt cod. Nothing remains of that industry but what is displayed here in Manchester-by-the-Sea. This multi-media exhibit’s outdoor fishyard includes the only American collection of authentic and reproduction fisheries equipment from the 1700s, and relates various aspects of the 1772 town and its people through video, illustrated text panels, and artifact displays. Learn More

Candlelight & Spiritualism Tours

Thursday, September 1 | 6 - 9 PM

Hammond Castle Museum

Candlelight Tours run at 6pm, 7pm and 8pm. Spiritualism Tours begin at 9pm. 

Candlelight Tours: Guides will escort visitors through the museum's many rooms, placing an emphasis on the Hammonds themselves and the time that they spent in their castle home. 

Spiritualism Tours: Delve into the history of the American Spiritualism Movement and the culture that formed around it, as well as the contributions of both Hammonds.

Learn More

Castle Hill Picnic Concert with Orville Giddings Band

Thursday, September 5 | 7 - 9 PM

The Crane Estate, Ipswich

Don't miss out on the last Castle Hill Picnic Concert of the summer with local favorite Orville Giddings Band. Gates open at 5 PM. Bring a picnic supper or purchase supper onsite from vendors Beefie Boys or Plat Du Jour and dessert from Down River Ice Cream or Q's Nuts. Mill River Winery, True North Ales, and 1634 Meadery will be selling beverages. Tickets are per car. Advance tickets are strongly recommended

What Time Is It Mr. Fox 

Friday, September 2 | 6 - 8:30 PM

Meetinghouse Green

Singer/songwriter 3rian King and the musicians of What Time Is It Mr. Fox deliver an electrifying performance with an evening of smoky cabaret, neo-soul, and acoustic noir. Their original songs feature rich lyrical imagery that explore love, spirituality, sexuality, and identity, and their performances are infused with energy, honesty, and emotional authenticity. Read More


The 7th Annual Great Gloucester GrowDown

Tuesday, September 20 | 6 - 8:30 PM

Short & Main, Gloucester

Join Backyard Growers and their awesome community at the 7th Annual Great Gloucester GrowDown! Proceeds from this blow-out fundraiser support Backyard Growers' work cultivating healthy, connected, resilient communities by empowering people to grow their own food. The event will feature entertainment, a live video premiere and fund-a-need auction.

Buy Tickets 

Cape Ann Ongoing Events 


  • Appleton Farms: Check out all events, from Farmhouse Culinary Workshops to Fire Pit Picnics to Hikes for Beer!
  • Hammond Castle: Gloucester Gratis Days every Tuesday. Self-guided tours daily.
  • Rockport Exchange: Farmer's Market every Saturday through October 15th from 9 AM to Noon in Harvey Park
  • Schooner Adventure: Weekend public sailings with free sails for children

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