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Membership Drop-In Hours
Tuesday | 10 AM - 12 PM
Members are invited to join us for Membership Drop-In Hours, a dedicated time for members to stop by and meet with Keri Conlon, Member and Visitor Services Manager. This is an opportunity to ask questions, review benefits, and discuss business concerns in a small setting. No appointment is needed! Learn More
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Gloucester Main Street Block Party
Friday, September 4 | 6 - 10 PM
Join us for the last Gloucester Main Street Block Party on Friday, September 4, to kick off Labor Day Weekend. Enjoy music, shopping, food trucks, and more as Main Street shuts down for the evening.
Stage Sponsors: BankGloucester, Cape Ann Savings Bank, Institution for Savings
Gold Sponsors: Addison Gilbert Hospital/BILH, Applied Materials, Building Center, Endicott College
Silver Sponsor: A & A Services, Ebenezer Tax & Services, LeafFilter Gutter Protection
Supporting Sponsor: Cape Ann Lanes
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Business After Hours at Essex Historical Society & Shipbuilding Museum
Wednesday, September 9 | 5 - 7 PM
Please join us for our September Business After Hours at the Essex Historical Society & Shipbuilding Museum! Come catch up with your fellow Chamber members, forge new professional connections, and explore Essex’s rich maritime history and living shipbuilding tradition. Learn firsthand from Executive Director KD Montgomery about EHSSM's background, educational events, plans for the future, and more. Register Now
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Downtown Gloucester Listening Session
Tuesday, September 15 | 8:30 - 9:30 AM
Downtown Gloucester Businesses! Be a part of the conversation with the Greater Cape Ann Chamber, Discover Gloucester, and Ward 2 Councilor Dylan Benson
Join us for an informal listening session. This is an opportunity for us to hear directly from you - your priorities, concerns, ideas, and feedback on how we can work together to support Gloucester's vital downtown business community.
The objective is to foster communication and collaboration between the Chamber, the City, Discover Gloucester, and the business community to advance priorities, so your attendance and participation are important. Please RSVP to Colleen at colleen@capeannchamber.com or 978-283-1601.
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Small Business University
Increase the Value of Your Business
Thursday, September 17 | 12 - 1:30 PM
Whether you plan to sell your business in 5 years or 25 years, the work to maximize its value starts today.
Most small business owners spend years building their company but very little time preparing it to become a valuable, transferable asset. In this session, Tim Sanborn—who has participated in more than 65 business acquisitions and successfully built and sold his own company—will explain what buyers actually look for and what determines whether a business commands a premium price or struggles to sell. Presented by Tim Sanborn, Right Choice Business Solutions. Learn More & Register
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Swing into Fall: Businesswomen's Golf Event
Monday, Septmeber 21 | 8:30 AM - 1 PM
Rockport Golf Club
Please join the Businesswomen of Greater Cape Ann for our "Swing into Fall' Annual Golf Event at the Rockport Golf Club.
Newcomers are invited to start their day with basic instructions taught by Golf Pro, Steve Clayton at 8:30 AM. The Shotgun start will be sounded promptly at 10:00 AM for 9 holes of 'Scramble' format, to keep our foursomes moving at a good pace.
This event is for players of all levels- from first timers to accomplished players. There will be at least one experienced player in each foursome. Plan on enjoying a great day with other women while learning a game that is so important for 'doing business on the course'. Download Flyer | Register Now
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GET YOUR TICKETS TODAY!
39th Annual Greater Cape Ann Chamber Auction
Thursday, September 24 | 5 - 9 PM
Cruiseport Gloucester
You're Invited to Illuminate the Night! Get ready to ignite an unforgettable evening of giving, community, and energy at the 39th Annual Greater Cape Ann Chamber Auction.
This high-spirited night brings together local businesses, community members, and friends—all to support the Chamber's mission to promote local commerce, grow our regional economy, and bring impactful programs to life. When we shine together, our entire community grows brighter!
Our theme this year, Together, Let's Glow, reflects the incredible power of a united community. Each of us holds a spark, but together, we create a beacon of support for greater Cape Ann. Let's light up the future—together!
Get Tickets | Download Sponsorship Details
Radiance Sponsors: Beauport Hospitality Group; Cape Ann Savings Bank; Community Credit Union; Institution for Savings
Glow Sponsor: Johnson O'Connor
Spark Sponsors: Applied Materials; BankGloucster; Hammond Castle Museum; Law with Amy; R.W. Rogé & Company, Inc.; Seashore Comfort Solutions
Paddle Sponsor: Precision Roofing & Snowplowing
Photography Sponsor: Sassy Square Marketing
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$20K Game Tickets Now Available for Purchase
Drawing: Wednesday, October 28 | 5 - 7 PM
@ The Cut, with food by The Publick House
The $20K Game tickets are officially in the house and ready for sale!
There are 12 incredible chances to win, with a grand total of $20,000 in cash prizes up for grabs—including a $10,000 Grand Prize! Tickets are $100 each, and we are strictly limiting sales to just 400 tickets, giving you excellent odds to win.
How to Get Your Tickets
Online: Visit https://bit.ly/20KGame
In Person: Purchase directly from Chamber Board Members or your favorite local seller.
The live drawing takes place on Wednesday, October 28, 2026, from 5:00 PM to 7:00 PM at The Cut in Gloucester. You do not need to be present to win, but seating is limited if you'd like to join the fun.
Special thanks to our Presenting Sponsor, Seashore Comfort Solutions!
| | Member & Community Events | | |
On-Going Events
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Wake Up Spirit: Sunday, September 6 @ 11 AM | Floating Lotus Gloucester
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Rockport Exchange Farmer's Market: 9 AM - 1 PM in Harvey Park, Rockport | Every Saturday through October 10
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Cape Ann Lanes & Laneside Pub & Brewery:
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Music Video Bingo - Join us every Tuesday in our Laneside Pub & Brewery for Music Video Bingo!
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Ladies Night - Every Wednesday night all summer long
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Unlimited Cosmic Bowling: Thursday Night Special
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Backyard Growcery: Every Wednesday | 2:30 - 6:30 PM | Burnham’s Field, Gloucester
- Rockport Art Association & Museum
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Small Works 3 — Juried Artist Members: through September 13
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Museum Fundraiser: Collector's Sale: through September 27
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Impressions of the New England Landscape: through October 18
- Rocky Neck Art Colony: Weekly Life Drawing Workshops, Mondays, 1 - 4 PM
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Fiber Arts Circle: Wednesdays at Manchester Public Library, 2 - 3 PM
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Cape Ann Foodie Tours presents Beauport Hotel Taste of Gloucester Tour: Every Thursday, Friday & Saturday, 11:30 AM - 2:30 PM, starting at the Beauport Hotel
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Literary Gloucester, A Walking Tour: September 5, 19
- Beauport Hotel
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Birdseye Rooftop Live Music Access: Bringing live music every Sunday-Thursday on the Birdseye Rooftop at Beauport Hotel with craft cocktails and unbeatable views.
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Sunset Sessions on the Birdseye Rooftop: Spend your weekend nights on Beauport Hotel's Birdseye Rooftop with stunning views, lively tunes and savory cocktails! Friday & Saturday nights.
- The James Pub & Provisions Events, Essex
- Burger & Beer Night Mondays $20
- Trivia Night Tuesdays
- Live Music Fridays, Saturdays, and Sundays
| | 42nd Annual Gloucester Schooner Fest | | |
From Thursday, September 3rd, through Sunday, September 6th, 2026, Gloucester Harbor will come alive with the sight of magnificent schooners under sail. This Labor Day tradition draws vessels from near and far for parades, sails, deck tours, and the Mayor's Cup Races.
Hosted by Maritime Gloucester, the festival is your chance to get up close to these historic ships and be part of a celebration that has captivated thousands for over 40 years. Plan your weekend on and off the water and join us for a truly unforgettable experience!
DOWNLOAD 2026 PROGRAM | VIEW SCHEDULE ONLINE
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Themed Public Sail!
Sundays through September 20 | 11 AM - 1:30 PM
Schooner Adventure
Harriet Webster Pier | Maritime Gloucester
Sunday Themed Sails offer deeper interpretive journeys into Gloucester’s history. These thematic experiences trace a compelling narrative arc across the summer, from the birth of the Gloucester schooner and life on the Banks, to the global cod trade, artistic and literary connections, and ultimately the decline and preservation of the fishing schooner era. The season culminates in reflections on Adventure’s own story, including “Saving Adventure: A Ship Reborn” and “100 Years of Adventure.” Learn More
Public Sails
Fridays in September | 4 - 6:30 PM
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Schooner Festival Cruise Schedule aboard WEJACK
Thursday, September 3 - Monday, September 7
Join us aboard the legendary Gloucester Fishing Yacht, the Wejack to see all the visiting Schooners up close from the water. The Wejack has a full bar aboard. We have multiple trips offered daily during the Schooner festival that will be a boatload of fun! See the Calendar and schedule of events below to learn more about our trips offered for the Schooner Festival. The Wejack is a classic power/fishing vessel that you’ll fall in love with, and is not a schooner, but is the perfect spectator boat to get the best views. Learn More & Buy Tickets
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Cape Ann Guitar Society Folk Week 2026
Join Cape Ann Guitar Society for their second annual Folk Week - four nights of independent artists playing new and ancient folk music from Brazil, Europe, and Cape Ann.
Brasil Sonoroso in Concert
Thursday, September 3 | 7 - 9 PM
St. Anthony's by the Sea, 21 Farrington Ave, Gloucester
Wood and Bone with Kicked Off the Bus
Friday, September 4 | 6:30 - 9:30 PM
Windhover Center for the Performing Arts, Rockport
Henry Acker Trio
Saturday, September 5 | 7 - 9 PM
MAGMA, 11 Pleasant St Ste 64, Gloucester
Ramon Tasat in Concert
Sunday, September 6 | 4 - 6 PM
St. Anthony's by the Sea, 21 Farrington Ave, Gloucester
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Opening Reception - Landings 3 Visions
Friday, September 4 | 5 - 7 PM
Cape Ann Cosmos Gallery, 20 Pleasant St., Gloucester
From the Renaissance through Impressionism and abstraction, artists have interpreted the landscape. In contemporary painting, the landscape may remain recognizable—or become only the point of departure. LANDINGS 3 VISIONS brings together three accomplished New England artists whose paintings explore the territory between observation and interpretation. Land, sea, forests, rocks, harbors, boats, and the built environment provide subjects, but the artists’ individual ways of seeing—and painting—transform them. Learn More
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Beauport Cruiselines Labor Day Weekend Fireworks Cruise
Saturday, September 5 | 7 - 10 PM
Step aboard for an evening of breathtaking views as we cruise through the scenic Gloucester Harbor at sunset. Enjoy a decadent Prime Rib dinner buffet featuring delicious seasonal favorites, sip handcrafted cocktails from our cash bar, and dance the night away with live DJ entertainment on board. As the evening reaches its grand finale, sit back and take in a dazzling fireworks display from the best seat in town — right on the water beneath the sparkling night sky. Whether you’re celebrating with family, friends, or a special someone, there’s no better way to send off summertime in New England. Get Tickets
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Backyard Growers 11th Annual Growdown
Thursday, September 10 | 6 - 9 PM
Oak to Ember, Gloucester
Join Backyard Growers for farm-fresh dinner, drinks & fun at the 11th annual GrowDown! Let’s celebrate another successful growing season in our community! All proceeds support food equity programs in Gloucester’s neighborhoods, schools, and beyond. The event will feature entertainment, delicious farm-fresh dinner & drinks from Oak to Ember, a live video premiere and fund-a-need auction. Get Tickets
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Gloucester Stage Company presents MOON MAN WALK
Opening Night | Thursday, September 10 | 7:30 - 9 PM
Runs through September 26
Travel to the moon and back as Spencer revisits his childhood home in Philadelphia following his mother’s passing. With the help of the unfettered Petrushka, along with the haunting memory of his mother, Spencer dives into the mystery of his youth and uncovers the true identity behind his estranged father. Journey through time and space as we discover how our pasts shape, protect, and connect us all in this time-bending, regional premiere drama. Written by Pulitzer Prize winning playwright James Ijames.
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Marini Farm Corn Maze Adventures 2026!
Opening Day | Saturday, September 12 | 10 AM - 6 PM
Open Saturdays and Sundays through October
Our Corn Maze is not your typical walk through the stalks – it is educational and interactive. There are 18 stations strategically placed throughout the maze with answers to a game sheet that you will be given before entering. We don’t give you clues…you need to find your way out on your own! You will be able to track your progress through the maze by the amount of answers you find on your game sheet. A finished game sheet is a finished maze! For our youngest adventurers, we also have a 1 acre/20 minute “mini maze”. Their very own 5 stations scavenger hunt awaits. Learn More and Get Tickets
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Rockport Art Walk Second Saturdays
Saturday, September 12 | 4 - 7 PM
Art, artists, refreshments, shopping, and ocean views—what more could you ask for? Join us on the Second Saturday of every month for our Art Walk and experience a vibrant evening filled with creativity, conversation, and coastal charm.
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Cape Ann Pride's Masquerade Ball
Saturday, September 12 | 7 - 10 PM
Castle Hill on the Crane Estate
An evening of mystery and queer glam at one of the most beautiful settings - the Great House at Castle Hill, with the Grand Allee stretching out toward the ocean. Masks encouraged, formal/semi-formal attire welcome - come dressed to celebrate in whatever way makes YOU feel glamorous and festive! Enjoy a full cash bar, seasonal hors d'oeuvres by Fireside Catering, and live music from the acclaimed Suzuki School of Newton String Quartet. Get Tickets
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Pins for Pets Fundraiser
Sunday, September 13 | 4 - 6 PM
Cape Ann Lanes
Join us for Pins for Pets, a fun-filled bowling fundraiser benefiting STAY Pet Services — a program of Senior Care Inc. dedicated to helping older adults keep their beloved pets.
Whether you're a seasoned bowler or just in it for laughter, you'll enjoy an afternoon of friendly competition, and plenty of opportunities to make a difference. Start a team, cheer on your friends, enter to win exciting raffle prizes, and help ensure that no older adult must choose between caring for themselves and caring for a beloved pet. Reserve Your Spot Today
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Commonwealth Payroll & HR Webinar:
What Your Employees’ Attorneys Know (That You Don’t)
Tuesday, September 15 | 1 - 2 PM
Could one routine workplace decision become the claim you never saw coming?
Here’s a statistic: In 2024, the U.S. Equal Employment Opportunity Commission (EEOC) received 88,531 new discrimination charges, up 9.2% from the year before, and recovered nearly $700 million for workers. Behind every one of those numbers is a decision that felt routine to the employer and worth pursuing to the employee.
Join CommPayHR for a candid conversation with attorneys who represent employees and see, up close, where employer decisions, documentation gaps, and compliance missteps turn into legal exposure. Register to Attend
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Homeschool Adventures: Session 1
A 4-class series program
Tuesdays, September 15 through October 6 | 1 - 4 PM
Crane Estate & Appleton Farms, Ipswich
Young explorers are invited to join us in September & October for a 4-part homeschool series that will get them active & moving with nature adventures, exercise, and outdoor skill building. While exploring Appleton Farms & the Crane Estate, participants complete active adventures & design challenges that will exercise both their body & mind. Some potential activities include kayaking, tide pooling, wetland exploration, orienteering, gardening, obstacle course design, and more!
This is a drop-off program that is open to ages 5-11 and will include small group activities based on age and peer mentoring opportunities between age groups. Learn More & Register
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Creative CHIXX Conference 2026
Thursday, September 17 | 9 AM - 5 PM
Floriana, Ipswich
Owning a small business can sometimes feel like you're supposed to know how to do everything. You are not. The Creative Chixx Conference was built for women who want real ideas, real connections, and real help moving their business forward. Success is better when it's shared. Come find your people, your inspiration, and your next big idea at Creative ChiXX 2026. Learn More & Get Tickets
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The Savvy Caregiver
Thursday, September 17 | 11:30 AM - 1:30 PM
Essex Council on Aging
The SAVVY Caregiver is a free 6-week workshop is for caregivers of memory-impaired recipients, meets weekly and will help caregivers understand the impact of dementia, learn skills to manage daily life and communicate more effectively, and take care of themselves. Taking care of a person living with Alzheimer’s or related dementia is specialized work. To do this work successfully, caregivers need special skills, knowledge, and a positive attitude that helps them care for themselves. Learn More
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We extend a big thank you to our supporting sponsors.
If you are interested in promoting with the Greater Cape Ann Chamber of Commerce and sponsoring this newsletter, please contact Sam Bevins at sam@capeannchamber.com
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