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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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Rockport Harvest Fest
Saturday, October 17 | 11 AM to 5 PM
Downtown Rockport
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!
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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
Visit bit.ly/EssesxClamFest to see list of vendors, foods & entertainment.
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!
| | Member & Community Events | | |
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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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 Pecks Solo Art Show: through October 155
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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
- 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
| | Please note that the Rocky Neck Art Colony Beaux Arts Ball Halloween Bash has been canceled. | |
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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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Woodman's Weekday Specials & $8 Kids Meals All Day Every Day!
October 13 through May 7, 2027
L. Dexter Woodman Family Foundation - Restaurant Night
Wednesday, October 14 | 11 AM - 10 PM
The James 55 Main St. Essex
Join us at The James for lunch or dinner and The James will generously donate a percentage of the proceeds from the entire day to the Foundation! Live music by Jeff Fraser.
Please note that the L. Dexter Woodman Family Foundation - Left Right Center Fundraising Tournament has been postponed.
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Leo Mancini-Hresko – Portrait Painting Demonstration
Wednesday, October 14 | 6 - 8 PM
Rockport Art Association & Museum
Join Leo Mancini-Hresko for a portrait demonstration exploring his approach to painting the human head and how it closely parallels his method for painting the landscape. Over the course of the demonstration, Leo will discuss local color, light and shade, and the importance of working from the general toward the specific in order to achieve a strong likeness. Throughout the demo, Leo will be happy to answer questions, and a selection of his portrait work will be on view during the event.
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Small Talks: Connecting with your 9-11 year old
Thursday, October 15 | 5:30 - 7 PM
Cape Ann YMCA
Sponsored by the City of Gloucester Health Department
What: Caregiver classes & coaching
For Who: Parents & caregivers of 9-11 year olds
To Gain:
- Confidence & skills to talk with your youth
- Readiness to navigate adolescence
- Family-to-Family support
Cost: Free registration & refreshments
When: Thursdays 5:30-7pm (through November 19)
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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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Taste Gloucester Food Tour
Saturday, October 17 | 11:30 AM - 2:30 PM
Cape Ann Foodie Tours
Taste Gloucester guests will make their way on foot through downtown Gloucester sampling food from five or six local vendors during this award-winning foodie tour.
From delicious local chowder, authentic Italian cannoli, to a sandwich that Gloucester natives have been enjoying for decades. This tour will expose you to local treats you’d be hard-pressed to discover on your own. Along the way, our dynamic tour guides will provide the backdrop to this 400-year-old city with great stories and interesting facts about the oldest working seaport in America. There will be no room for lunch after this tour as we make sure you leave “full” of knowledge! Book Online or call 617-902-8291.
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City of Gloucester Halloween Party
Saturday, October 17 | 12 - 3 PM
Stage Fort Park
A free event for kids of all ages!
🚜Haunted hayride
🚒 Touch a truck
🍬Candy parade
🍿Popcorn and snacks
🎉Everyone's favorite - DJ LEO!!
💧 Please bring a water bottle - water will be provided
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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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Marini Farm, Ipswich
Pumpkin, Pints and Pianos
Friday, October 23
An ALL-NEW fall tradition is coming to Marini Farm! Join us on Friday, October 23rd for an unforgettable Friday Night Family Festival featuring Dueling Pianos LIVE under the stars!
🎹 Live Dueling Pianos Show: 7:00 PM – 9:00 PM
🌽 Maze Park & Corn Maze: 6:00 PM – 10:00 PM
🔥 S’mores & Concessions: Available throughout the evening
Hallow-Marini Party
Saturday, October 24 | 12 - 3 PM
Sunday, October 25 | 12 - 3 PM
Families will find Halloween fun at Marini Farm in Ipswich! By popular demand we are hosting another kid's Halloween event! We welcome everyone to join in on the fun and dress up. There will be a DJ, Dance Party with Characters and Trick or Treat Candy Drop!
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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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