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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; Seashore Comfort Solutions
Paddle Sponsor: Precision Roofing & Snowplowing
Photography Sponsor: Sassy Square Marketing
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On-Going Events
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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
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Blessings by Ruth Mordecai Collages and Paintings at Cape Ann Cosmos Gallery - through August 30
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North Shore Arts Association: Jeff Weaver Solo Show, through August 30
- 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
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Emerson Inn Moonrise Party
with Lois Lane and the Daily Planets
Thursday, August 27 | 5 - 9 PM
Join us at the historic Emerson Inn for an evening of elegance. Sip on crafted, moon-themed cocktails and enjoy a delicious menu of seasonal bites, along with live music by Lois Lane and the Daily Planets as we watch the red moon rise over the Atlantic. Reservations required: Call (978) 546-6321 or Reserve Online
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Castle Hill Picnic Concert
Thursday, August 27 | 6:30 - 8:30 PM
Join The Crane Estate for the last picnic concert of 2026, featuring hometown favorite Orville Giddings Band. Bring a picnic blanket or lawn chair and set up on the lawn. While here, explore the gardens, walk the 1/2-mile-long Grand Allee, try a landscape-themed eye spy, picnic, and dance on the grass.
Bring a picnic supper or purchase supper onsite from vendors Beefie Boys or The Lobster Roller and dessert from DownRiver Ice Cream or Q’s Nuts. Mill River Winery, True North Ales, and 1634 Meadery will sell beverages each week. Outside alcoholic beverages are not permitted and parcels will be searched upon entry. Get Tickets
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Challenge Course Admin 101 (Online Webinar)
Friday, August 28 | 12:30 - 2:30 PM
Whether you're new to overseeing a challenge course, ropes course, or climbing wall, or looking to strengthen your administrative foundation, Challenge Course Admin 101 is your guide to the essential systems and responsibilities that keep your program running smoothly and safely.
PE Activity Refresher
Tuesday, September 1 | 12 - 3 PM
Looking for inspiration and a fresh take on PE activities with your classes? Look no further than Project Adventure’s Phys Ed Activity Refresher!
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Pints & Ponytails
Thursday, August 27 | 6 - 8 PM
Cape Ann Lanes & Laneside Pub and Brewery
Hands-on hair styling workshop
Includes class with professional stylist Cathi Gelfand of Mirror Beauty Studio.
Mannequins to practice on.
Tools to use and goody bag to take home.
Pint of beer from Laneside Pub & Brewery.
Leave with new skills and serious Dad points!
Get Tickets
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Jimmy Keys Benefit for "Friends for Friends" Charity
Thursday, August 27 | 6 - 10 PM
Gloucester Fraternity Club
Jimmy Keys - International Musical Comedy Entertainer. Non-stop high energy entertainment. Benefit for "Friends for Friends" Charity--a nonprofit organization that donates comfort bags monthly to Addison Gilbert Hospital in Gloucester. Admission is $50 per person and includes a buffet dinner and the show. Text or call 508-843-3320 for tickets.
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Full Moon Sail
Friday, August 28 | 8 - 9:30 PM
Schooner Thomas E. Lannon
The harbor has a different kind of feeling under a full moon. Join us for an evening sail as the water catches the light and everything slows down just enough to remind you why you love summer on the North Shore. Peaceful, romantic, and honestly — just really good for the soul. Book the Sail
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Essex River Day
Saturday, August 29 | 5 - 9 PM
Shepard Memorial Park
Essex River Day is Back! The Locals of Essex invite you to celebrate our amazing town and river at Shepard Memorial Park on Saturday, August 29 from 5 PM to 9 PM! Grab the family and join us for a wonderful, free community event. Here is what is on deck:
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Live Acoustic Music: Enjoy sets from rising MERHS senior Maggie Whitman, covering hits from the 1960s to today.
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Food: Grab savory or sweet bites from the Crepes du Jour food stand.
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Local Brews: True North Ale Company will be serving up refreshments, including their Coast to Coast American Summer IPA, white wine blends, and non-alcoholic choices.
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A GIANT Bonfire: Cozy up when dusk arrives to watch the community bonfire take flight, fueled by local donations, and topped with a giant GREEHEAD.
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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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Builder Spotlight: A&A Building and Remodeling
Tuesday, September 1 | 4:30 - 5:30 PM
90 Park Street, Beverly or Virtually
Join WORKS By JD as we welcome A&A Building and Remodeling for our next Builder Spotlight. This event brings together builders, remodelers, architects, designers, vendors, and local industry professionals for a practical conversation around craftsmanship, collaboration, and quality residential construction.
A&A Building and Remodeling will share insight from their work in custom homes, renovations, remodels, outdoor living spaces, and architectural window and door installation.
With AIA CEU credit included, this event offers both professional learning and local industry connection. Guests may attend virtually or in person at the WORKS office. Register Now
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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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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
| | 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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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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