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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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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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Rockport Harvest Fest
Saturday, October 17 | 11 AM to 5 PM
Downtown Rockport
The Greater Cape Ann Chamber of Commerce is excited to bring back Rockport’s Harvest Fest, a cherished community event, for another year! Join us by the shore for a unique blend of fall festivities and coastal charm, where the crisp sea breeze meets the warmth of community spirit. Enjoy Rockport’s local charm and bountiful harvest while you explore scenic downtown and immerse yourself in festive seasonal activities. Whether you’re a longtime local or just visiting, this is the perfect way to experience the magic of autumn by the sea. So, grab your sweater and your loved ones, and join us for a day of seaside celebration!
2026 Event Highlights
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Apple Pie Bake Off: Join our host, Rick Doucette, and come cheer on local amateur bakers as they compete for the title of best apple pie! (Entries still open!)
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Hometown Entertainment: Enjoy live performances from local musicians
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Local Vendors: Discover unique artisan goods and seasonal treats.
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Family Fun: Bring the kids and explore seasonal crafts, games, face painting, and a live animal exhibit!
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Seaside Bites and Brews: Savor seasonal favorites, local cuisine, and beer.
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Shopping: Enjoy the rich artistic culture and plentiful selections of our local retailers.
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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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41st Annual Essex ClamFest
Saturday, October 24 | 11 AM - 4 PM
Clam Chowder Contest: 12 PM - 1 PM (or while supplies last)
Shepard Memorial Park
Join us at the Essex ClamFest, Arts & Crafts Festival in Shepard Memorial Park in Essex. Come taste Cape Ann's finest chowders from Noon to 1 pm and vote for your favorite! (Tasting only while supplies last) While the highlight of the day is the Chowder Tasting Competition, there are also a variety of activities, including arts and crafts vendors, live entertainment, and plenty of on-site food vendors!
Chowder Competition's Participating Restaurants:
- 35 Beach
- Addison Gilbert Hospital - Sodexo
- Castle Manor Inn
- CK Pearl
- Machacha Taco & Tequila Bar
- The Burn
- The Farm
- The James Pub & Provisions (2025 Winner)
- Woodmans of Essex
Important Note: Martin Street will be closed in one direction for increased on-street parking. Parking is also available at Essex Elementary School on Story Ave, with a free shuttle bus (sponsored by Beauport Limousine) running every 10 minutes.
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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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On-Going Events
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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: LAST FARMER'S MARKET OF 2026! 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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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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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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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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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 Artisans Fall 2026 Open Studios
Saturday, October 10 | Sunday October 11
Download Brochure
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.
Participating Artists:
Nina Goodick | Anniqaum River Pottery: Functional Pottery
Jacqueline Ganim-DeFalco: Sea Glass Wearable Art, Garden Stones & Sculpture
John Abisamra: Fine Art Photography
Tina Frassica: Quilting
Katrina Abbott: Pottery and Textiles
Sara Wright: Handwoven and Knit Accessories
John Bassett: Eco-Friendly recycled glass art*
Pam Stratton: Mosaics, Mixed Media, Eco Printed silk scarves, Jewelry, Sculpture
Rob Diebboll: Oil and Water Color Painting
Kathryn Roberts: Watercolor Painting
Cindy Efinger: Mosaic and Sculpture
Jane Keddy: Textiles, Prints, and Mixed Media*
Visitors can also learn more about the open studios in the Media Announcement.
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Make and Move Series: Glutes and Totes Edition!
Saturday, October 10 | 10:30 AM - 12 PM
Island Stretch & Strength, 261 Main St, Gloucester
Join Island Stretch & Strength for a fun morning of movement and creativity! This Make & Move event combines a 30-45 minute glute and core focused workout with a hands-on mini tote bag activity. We will utilize iron on patches to create a bag unique to you!
Participants will move through an approachable workout designed to build strength, improve mobility, and leave you feeling good—then wind down by creating a custom mini tote using iron-on designs. All fitness levels are welcome. Come for the workout, stay for the creativity and connection! Register Now
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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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Cape Ann Makers Market - Fall Market at Magtoberfest
Sunday, October 11 | 11 AM - 5 PM
Magnolia Library & Community Center
Jump start your holiday shopping at Cape Ann Makers Market's Fall Market. This Fall Market will feature 24 Cape Ann artisans, crafters and makers, showcasing handcrafted jewelry, photography, sea glass, stained glass, fiber arts, body care, artisanal salts and specialty foods, and so much more! Visitors can also stroll all along Lexington Ave and enjoy a classic car display, live music performances, a great line up of local food trucks, beer garden and other fun activities! See List of Vendors
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National Coming Out Day Meet Up
Sunday, October 11 | 4 - 5:30 PM
Saluti Wine Bar
Join us at Saluti in Gloucester in celebration of National Coming Out Day!
Meet and gather, share your story or just mingle with friends.
All are welcome!
Full bar and Saluti's menu available to order from
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401(k) Straight Talk for Employers
Commonwealth Payroll & HR Webinar
Tuesday, October 13 | 1 - 2 PM
Your 401(k) plan is more than a benefit. It can influence recruitment, retention, compliance and your organization’s financial strategy. Yet many employers are left sorting through competing advice, unfamiliar terminology and a growing list of responsibilities. Join our panel of experts for practical guidance on the importance of 401(k)s and walk away having a clearer framework for evaluating your plan and asking the right questions. What We WIll Cover
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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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Mapping Workflow, Not Titles: A REACH Leadership Roundtable
Wednesday, October 21 | 12 - 1 PM
Online Webinar
REACH Leadership Roundtables are open, facilitated working sessions designed for leaders to tackle real, day-to-day challenges while gaining and sharing insights with peers across organizations. We’ll dedicate this Roundtable to discussing:
1. What workflow mapping reveals that org charts and job descriptions can't
2. How title-based thinking creates gaps and overlaps in processes
3. Practical strategies for mapping work by function and flow, so responsibility follows the task rather than the role
Register Now
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Carol Lee's Cottage Pop Up Sale!
Saturday, October 24 | 11 AM - 6 PM
Brackett's Ocean View, Rockport
Come check out Unique Gifts, Art, Fashion & Housewares at Carol Lee's Cottage - Special Pop Up Sale. One Day Only!
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Rocky Neck Art Colony Beaux Arts Ball Halloween Bash
Saturday, October 24 | 6 - 10 PM
51 Rocky Neck Restaurant
Get ready for an unforgettable night of Halloween fun, creativity, and Rocky Neck style! The Rocky Neck Art Colony (RNAC) will host its third annual Beaux Arts Ball Halloween Bash. This is not your ordinary Halloween party.
Guests are invited to come dressed to impress—or dressed to surprise—for an evening filled with live music, dancing, passed hors d'oeuvres, a costume contest, prizes, and plenty of creative Rocky Neck spirit. Artists, friends, neighbors, and art lovers will come together for one of the Colony’s most festive celebrations of the year. 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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