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September 14, 2022

Featured Love Greater Cape Ann Live Auction Items

Gift certificate for private lighthouse rental for 2 people for 5 hours. Gift certificate includes private rental of the lighthouse tower for approximately 5 hours, hiring of your own personal wait staff, food, and a membership in The Lighthouse Preservation Society.

7 Night's Accommodations for 4 People in one of Tuscan Resort's 12 properties located in or close to Manciano Italy. Manciano is located 1 1/2 hours north of Rome and is a small hill town in the southern edge of Tuscany.

Visit Love Greater Cape Ann Fundraising Auction Preview

Chamber Events


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

Business After Hours Collaboration

Wednesday, September 21 | 5 - 7 PM

Your Hosts:

Cape Ann Savings Bank

(Gloucester Crossing Branch) 

Halyard Apartments

Glen T. MacLeod Cape Ann YMCA

Gather from 5 to 7 PM at the Cape Ann Savings Gloucester Crossing Branch, 4 School House Road for a networking party and raffles hosted by the three businesses! Take advantage of a guided tour of the YMCA and Halyard to gain extra entries into the raffles and see what they have to offer! 

Light appetizers will be served and drinks will be available for purchase.

Please register in advance if you plan to attend.

Download Flyer

NEXT GEN End of Summer Bonfire

Thursday, September 22 | 6 - 8 PM

Cape Ann Motor Inn

Hang out with other young professionals over drinks and light appetizers on a beautiful sandy beach in Gloucester. 

Cape Ann Motor Inn’s home on Long Beach is the perfect place to celebrate a successful summer and connect with old friends and new. Once the sun sets, we'll have a bonfire to gather around.

Please RSVP so we have an Idea of who to expect. No cost to join or participate, so bring a friend or partner!

RSVP Now | Download Flyer

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

Business After Hours

Appleton Farms

Thursday, October 6 | 5 - 7 PM

Join us at the Appleton Farms historic farmstead and learn about their mission and programming as you meet other chamber members and expand your network. 

Non-members encouraged to attend!

During our short presentation, we will also be celebrating our 1 year anniversary as the Greater Cape Ann Chamber and the merger with the former Ipswich Chamber. 

Download Flyer

Register 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. 

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New Member Special Advertising Section

Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings

Discover Gloucester

2022 Industry Roundtables Schedule

Retail: September 20 | 6:30 PM

Harbormaster Conference Room

Restaurants: September 21 | 3 PM

Minglewood Harborside

Arts & Culture: September 22 | 

Harbormaster Conference Room

Register Today

September Mug Up

Wednesday, September 14 | 5:30 - 7:30 PM

Cruiseport Gloucester

Join Discover Gloucester with Discover New England Executive Director Michele Cota for a discussion on the International Travelers' Market, followed by networking with industry colleagues.

Please RSVP if you plan to attend.

Paradise Blue

Performances Run through September 18

Gloucester Stage Company

Blue, a gifted trumpeter, contemplates selling his once-vibrant jazz club in Detroit’s Blackbottom neighborhood – it’s 1949 and gentrification is banging on the door. The house band is desperate to stay, Blue’s demons are tempting him to leave, and the arrival of a seductive stranger turns everything upside down. This dynamic and musically-infused drama shines light on the challenges of building a better future on the foundation of what our predecessors have left us. Learn More

Wednesday Evening Supper Club

Wednesday, September 14 | 4:30 - 6:45 PM

1606 Restaurant & Oyster Bar

Heading to Gloucester Stage Company to see Paradise Blue? Make it an entire evening of fun! We have partnered with GSC to host Wednesday Evening Supper Club: enjoy a specially curated 3-course Prix Fixe dinner at 1606 Restaurant & Oyster Bar with roundtrip shuttle transportation to and from Paradise Blue for an all-inclusive price of $63.50 per person.

Schooner Adventure

96th Anniversary Sail with Music by Dan King

Friday, September 16 | 5:30 - 7 PM

The culmination of the 2022 Music Sails features the sounds of Gloucester born and internationally known Dan King. All musical sails include complimentary beverages. BYO Picnics are encouraged.

Buy Tickets to 96th Anniversary Sail

Eat Local Raffle

Win a package of Cape Ann foodie experiences worth over $1000. Eat locally while supporting Schooner Adventure. Support Cape Ann businesses and culinary heritage while supporting our maritime heritage! Drawing to be held on the 96th Anniversary Sail, Friday, September 16, 4:30 - 7 PM. (Winner need not be present to win!)

Tickets: 1 for $20 or 6 for $100. Buy Raffle Tickets Here

Firebird Pops Orchestra:

Film Night at Hammond Castle Museum

Friday, September 16 | 7 - 9 PM

Hammond Castle Museum

The Firebird Pops Orchestra presents creative arrangements of beloved film music against the magical backdrop of Gloucester?s historic Hammond Castle Museum. Brendan J. Kenney conducts the chamber orchestra through the sweeping, magical scores of films and tv series such as Star Wars, Jurassic Park, Indiana Jones, Harry Potter, The Avengers, Game of Thrones, The Wizard of Oz, and more! 

Rockport Music

Shalin Liu Performance Center

Thursday, September 15 at 8 PM: Spyro Gyra

Friday, September 16 at 8 PM: Mike & Amy Aiken

Gloucester Downtown Clean Up

Saturday, September 17 | 9 AM | Burnham's Field

Get Active for a Cause This Saturday

Cape Ann Kids Pan Mass Challenge

Saturday, September 17

9 AM - 12 PM

Masconomo Park


Click to Learn More

Essex County Trail Association's Run for the Trails

Saturday, September 17

9 AM - 12 PM

Myopia Schooling Field


5 Mile / 10 Mile Trail Run

Men's & Women's Divisions

Race Day registration will be available, space permitting, for $5 additional

Click to Learn More

Tour de Greenbelt - Cycle for Land Conservation

Saturday, September 17

9 AM - 2 PM

Greenbelt's Cox Reservation


Event-day registration will be open from 7:30 to 8:4 AM

(6:45 AM for 100-mile riders)

Click to Learn More

Crow Fest 2022

Saturday, September 17 | 10 AM - 2 PM

Common Crow Natural Market

200 Eastern Avenue, Gloucester

A celebration of Common Crow, their local makers and farmers, and YOU (their brilliant customers) is back and in person. They couldn't be more excited! Rain or shine. Lean More

Bringing Women Artists of Cape Ann Online

Saturday, September 17 | 10 AM - 3 PM

Cape Ann Museum

The Cape Ann Museum Library & Archives and Sawyer Free Library are partnering to present Bringing Women Artists of Cape Ann Online. Inspired by the Art + Feminism initiative and the Cape Ann Museum’s upcoming exhibition on the Folly Cove designers, the organizations are coordinating a Wikipedia-a-thon to celebrate and share the incredible women artists of Cape Ann by updating their Wikipedia pages.  Free Registration Required

Jimmy Tingle Live - Humor for Humanity

Sunday, September 18 | 5 - 6:30 PM

Windhover Performing Arts Center

In Jimmy Tingle Live! HUMOR FOR HUMANITY, comedian, commentator and founder of Humor for Humanity, Jimmy Tingle mixes his funniest comedic hits and newest, post pandemic bits, to deliver the humor, hope and humanity the world so desperately needs in 2022. 

Click Here to Learn More  & Buy Tickets 

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 


Dry Salvages Festival: A celebration of T.S. Eliot

Saturday, September 24

Sunday, September 25

The Directors of the T. S. Eliot Foundation invite you to The Dry Salvages Festival to mark the connection between the Nobel Prize-winning poet and Gloucester, the home of his childhood summers, where he often said he was happiest. Join them in bird-watching and boat trips, tours of the Eliot house, an art exhibition inspired by his work and a performance of his most famous poems.


Marini's Farm Corn Maze and Play Area 

Opening September 10

Open 10 to 6 on Saturdays & Sundays in September.

Also open Friday nights 6 - 10 PM in October

Russell Orchards Apple Picking

Now Open to

Pick Your Own Apples






Farm Day Weekend at Appleton Farms

Saturday & Sunday

September 17 & 18

Games and activities for all ages, Wood-Fired Pizza and Food Trucks, Craft Beer Vendors, Animals & more

Cape Ann Ongoing Events 


  • Appleton Farms: Check out all events, from Farmhouse Culinary Workshops to Fire Pit Picnics to Hikes for Beer!
  • Cape Ann Museum: Learn about all the events, exhibitions, and talks happening at CAM.
  • Essex Shipbuilding Museum: Crossroads: Change in Rural America. Smithsonian traveling exhibit highlighting changing landscape of rural America in Essex, MA open through October 22.
  • 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


Glen T. MacLeod Cape Ann YMCA

2022 Golf Tournament

Monday, October 3

11 AM Lunch | 12 PM Shot Gun Start

Bass Rocks Golf Club

Hit the links for a great cause! The proceeds of the Glen T. MacLeod Cape Ann YMCA 2022 Golf Tournament will support all families and children of the Gloucester and Cape Ann communities.

The event includes lunch and dinner, 18 holes of golf (scramble format), on course games & contests, registration prize packages, putting contest, and a raffle. 

Please register at

Download Flyer

24th Annual Manchester-Essex Rotary Club Golf Tournament

Tuesday, October 4 | 12:30 PM Shot Gun Start

The Meadow at Peabody Golf Course

Peabody MA

$130 entry fee includes greens fee, golf cart, beverages, prizes, prime rib dinner ($50 for prime rib dinner only).

To benefit the Manchester-Essex Rotary Scholarship Fund. $100 Hole Sponsorships for local businesses.

To play or sponsor, contact Chris Shea (508-843-4979, or Dave Ray (978-921-2346,

Soundings Sponsors

Pivotal Partners

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