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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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MA House 2nd Essex District Candidate Forum 2026
Monday, October 5 | 6:30 - 8 PM
True North Ale Company
On Monday, October 5, the Greater Cape Ann Chamber of Commerce in partnership with Ipswich Local News and Hamilton Wenham News will host a Candidate Forum for State Representative for the Second Essex District on the November 3rd Election ballot.
The forum will be held at True North Ale Company from 6:30 to 8:00 PM. This event will be open to the public.
The candidates participating in alphabetical order are:
- Kristin Kassner (D) incumbent
- Daniel Kelly (R)
The candidates will each be given the opportunity to answer several questions on a wide range of topics. Please use this form to submit questions.
The event will be recorded by ICAM.
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Building Connections: An Ipswich Business Meet-Up
Wednesday, October 7 | 5 - 7 PM
Ipswich Country Club
Ipswich businesses are invited to join us for an evening of connection and opportunity at Ipswich Country Club!
Do you want to expand your network?
Are you looking for new opportunities for your business?
Are you interested in ways you can engage with fellow entrepreneurs and get more involved in our community?
Ipswich Division Chamber members are encouraged to invite non-member Ipswich businesses to attend this networking evening, to come meet the new Ipswich Town Manager, Brendan Sweeney, and enjoy light appetizers, a cash bar, and great connections. Engage with fellow and prospective chamber members and learn more about how we can work together for a stronger Ipswich business community.
Registration Required
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In-Person Coffee & Connections
Wednesday, October 14 | 8 - 9 AM
Chamber Office
Hosted by MassHire. Join us for a morning networking event where you can expand your business connections, explore resources, and discover new opportunities.
Register Today
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Business After Hours:
Cape Ann Savings Financial Advisors
Wednesday, October 21
Cape Ann Savings Bank, Gloucester
Join us for an evening of connection and conversation at Cape Ann Savings Financial Advisors! As a department of Cape Ann Savings Bank, CASFA is proud to unveil its fresh new brand following a recent rebrand from Cape Ann Savings Trust & Financial Services. Celebrate this exciting new chapter with them while enjoying a relaxed and welcoming evening of networking, relationship-building, and community.
Whether you’re a longtime Chamber member or new to the community, this is a wonderful opportunity to connect with fellow business leaders from across the region.
Register Now: Free for members | $15 for non-members
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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!
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Thursday, October 1 | 1 - 7:30 PM
Ribbon Cutting at 4:30 PM
Join us as we celebrate the Grand Opening of Ipswich River Craft in Essex!
Come tour their new studio in their brand new location and explore their unique brand of nautical gifts, specializing in hand-crafted and custom painted nautical alphabet flag signs!
Enjoy light refreshments while you browse an array of nautical inspirations from other local artisans and see how your name appears in the "secret" nautical alphabet. Observe live demos of gold leaf application. Custom orders welcome!
Special! Offering 20% off nautical flag block signs during the open studio.
| | | | Member & Community Events | | |
On-Going Events
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Wake Up Spirit: Sunday, October 4 @ 11 AM
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Marini Farm Corn Maze Adventures 2026: Open Saturdays and Sundays through October
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Pumpkin Sale: West Gloucester Trinitarian Congregational Church, 488 Essex Ave
- Monday - Friday: 3 - 6 PM
- Saturdays:9 AM to 6 PM
- Sundays: noon to 6 PM
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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, through September 30
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Fair Winds and Following Seas: Matthew Allen & Zelda Rohrbach Mayer: Through December 20 at Thalassa Gallery
- Rockport Art Association & Museum
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Bethany Peck's Solo Show: through October 12
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Impressions of the New England Landscape: through October 18
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Small Works 4 - Juried Artist Members: through November 1
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Fall Exhibition – Juried Artist Members: through November 8
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Riding the Waves: Art of the Schooner Adventure: through November 8
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Landings 3 Visions: Cape Ann Cosmos Gallery, through October 11
- 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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Woodman's Weekday Specials & $8 Kids Meals All Day Every Day! October 13 through May 7
- The James Pub & Provisions Events, Essex
- Burger & Beer Night Mondays $20
- Trivia Night Tuesdays
- Live Music Fridays, Saturdays, and Sundays
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1926: A Year in the Life of Hammond and His Castle
Wednesday, September 30 | 5:30 - 7:30 PM
Hammond Castle Museum
One hundred years ago, John Hays Hammond Jr. embarked on one of the most ambitious projects of his life: building Hammond Castle Museum. But why construct a brand new medieval-inspired castle after already transforming his previous home into a castle-like residence? And why was Hammond absent during the first year of construction, entrusting oversight of the project to one of the Hammond Research Laboratory's engineers? Learn More & Get Tickets
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Fall Cider & Donut Cruises
Weekends in October
Essex River Cruises and Charters
Embark on a journey to experience the award-winning flavors of Fall in New England! Cruise near Hog/Choate Island and behold the mesmerizing dark spruce forest. Watch as nature paints the landscape with brilliant hues of yellow and orange. Treat yourself to complimentary hot cider and delectable donuts from the acclaimed Russell Orchard of Ipswich. Join us for an unforgettable adventure amidst New England's most magnificent fall foliage.
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Reception for 3 New Exhibitions
Saturday, October 3 | 1 - 3 PM
Rockport Art Association & Museum
Join us for our reception for the following new exhibitions:
Bethany Peck Solo Show: September 26 - October 15
Riding The Waves: Art Of The Schooner Adventure – Juried Artist Members: September 26 - November 8
Fall Exhibition – Juried Artist Members: September 26 - November 8
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Cape Ann Plein Air
October 3 - 11, 2026
Cape Ann Plein Air week brings 36 juried artists to the coastal landscapes of Cape Ann, Massachusetts, where they paint through the week & compete for awards & prizes. Join us for live demonstrations, a Quickdraw competition with over 100 artists, opening reception, our Gala & Art Sale, & judges' talks.
Please visit the Cape Ann Plein Air website for the detailed calendar of events.
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"Tails on the Trails" presented by Cranney Home Services
to benefit Cape Ann Animal Aid
Saturday, October 4 | 10 AM - 2 PM
Dogtown Woods, Gloucester
Get your Tail on the Trails! Join Cape Ann Animal Aid for a 2.6-mile hike in Dogtown Woods with your pup to fundraise for Cape Ann Animal Aid! Register for this event, and then create your own fundraiser to keep the good momentum going! All funds raised will support homeless animals at Cape Ann Animal Aid.
Visit capeannanimalaid.org/walk for more information and to sign up to walk!
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Cape Ann Cake Fest
Sunday, October 4 | 2 - 4 PM
Windhover Center for the Performing Arts, Rockport
Hosted in support of The Open Door and Windhover Center for the Performing Arts, Cape Ann Cake Fest brings bakers of every kind — home bakers, bakery-bought, the ambitious and the just-here-for-fun — together for one afternoon of sampling, swapping, and second helpings. Bring a cake, leave with a box full of new favorites, and help support two organizations doing vital work on Cape Ann. Learn More
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Cape Ann Toastmasters Open House
Tuesday, October 6 | 7 - 9 PM
Cape Ann Savings Bank Community Room
123 Main Street, Gloucester
Curious about Toastmasters? Come see what we’re all about! Cape Ann Toastmasters is a local public speaking club where people come together to build confidence, improve communication skills, practice speaking in front of others, and develop leadership skills in a supportive, low-pressure environment. Our Open House is a great opportunity to visit, meet members, see how a Toastmasters meeting works, and learn whether the club might be a good fit for you. Learn More | Register Now
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North Shore Alliance Policymaker Series Featuring Dr. Stephen Zrike Jr., Secretary of Education
Wednesday, October 7 | 9 - 10 AM
18 Washington Square Salem
Secretary Zrike will provide an update of the Healey-Driscoll Administration Education initiatives statewide and for our region. Registration is required to attend.
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CAM Studio Art: Design and Print the Folly Cove Way
Wednesday, October 7 | 1 - 4 PM (Runs for 4 Sessions)
CAM Education Room, Downtown Campus
Step into the spirit of the legendary Folly Cove Designers and learn the art of block printing with artist Mary Rhinelander in this four-week course. This class blends design fundamentals, creative play, and the rich history of Cape Ann’s iconic design collective. Referencing her unpublished book, Design and How, you’ll explore the principles of design that Virginia Lee Demetrios taught her students—selecting a theme and exploring it deeply through clarity of line, rhythm, repetition, and pattern—and you will discover how her timeless ideas can elevate your own artistic voice. Each week builds your confidence as you sketch, carve, and print your way towards an original finished artwork. Learn More & Register
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A'mi Nail Studio Grand Opening Open House
Thursday, October 8 | 4 - 6 PM
17B Beach St., Manchester-by-the-Sea
Join us as we celebrate the opening of A'mi Nail Studio in beautiful Manchester-by-the-Sea! Come browse the new studio and enjoy light refreshments. Raffles and a special promotional offer for the first 20 guests!
A'mi Nail Studio: beautiful nails, thoughtfully done. Organic care and modern technique, in a calm, spa-like space designed around you. Learn More
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Harborlight Homes - Journey Home 2026
Thursday, October 8 | 6 - 8 PM
The Historic Theatre at Beverly Village for Living & The Arts
20 Colon Street, Beverly
Join us for Harborlight Homes’ most meaningful Journey Home yet; our first event hosted in a community your generosity helped create. It's going to be an evening to inspire. Great food, inspiring stories, and a first look at how your support is transforming lives across the North Shore. Learn More
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Cape Ann Plein Air Gala and Art Sale
Friday, October 9 | 6 - 8 PM
North Shore Arts Association, 11 Pirates Lane, Gloucester
Celebrating 10 years. 36 artists. 175+ paintings. One unforgettable night. Sip, snack, and shop original art fresh off the easel — then meet the artists who made it and see who won awards. Live music + open bar + light refreshments by Timothy Hopkins catering. Buy Tickets
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Cape Ann Artisans Fall 2026 Open Studios
Saturday, October 10
Sunday October 11
Explore the creativity, craftsmanship, and coastal inspiration of the talented artisans featured in the Cape Ann Artisans Fall Open Studios 2026! This year’s tour showcases an exciting variety of artistic styles and mediums. Visitors can also learn more about the open studios in the Media Announcement.
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Rockport Art Walk Second Saturdays
Saturday, October 10 | 4 - 7 PM
Last ArtWalk of the Season!
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. Visit rockportartwalk.com for list of participants.
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Stepping Up for SeniorCare!
54th Anniversary Celebration
Thursday, October 15 | 5:30 - 8 PM
Beauport Hotel
SeniorCare's 54th Anniversary Celebration, marking over five decades of dedicated service to our community, will be Thursday, October 15, 2026, in the beautiful Beauport Hotel Grand Ballroom overlooking Gloucester Harbor.
Join us for an unforgettable evening of celebration and support for SeniorCare’s vital services for older adults! Enjoy a buffet dinner, cash bar, exciting raffles, and awards as we honor our Community Heroes:
- Lenny & Dottie Linquata, Myra L. Herrick Outstanding Older American Award
- Sheila Taylor, Rosemary F. Kerry Community Service Award
Get Tickets
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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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