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October 19, 2022

Today is Support Your Local Chamber of Commerce Day! Thank you to our members and volunteers who help make our chamber great!

Chamber Events

$25K Game Official Drawing 

featuring Halloween/Harvest theme.


Thursday, October 20 | 5 - 7 PM

Gloucester Elks


NEW! CHILDREN INVITED & COSTUMES ENCOURAGED!!  Children and costumes are welcome and there will be a goodie bag for all kids plus a prize for best costume (for both kids and adults).


Calling all ticket holders! Join us at the Gloucester Elks for the $25K Game Official Drawing! There is limited seating available, so please reserve your spot today by email or by calling 978-283-1601.

38th Annual Essex ClamFest

Saturday, October 22 | 11 AM to 4 PM

Memorial Park, Essex 

(Rain Date: Sunday, October 23)

Come taste Cape Ann’s finest chowders! Although the highlight of the day is the Chowder Tasting Competition, there is a great variety of activities, including arts and crafts vendors, live music by Unchartered Watahs and Daisy Nell & Capt. Stan, and plenty of food vendors on-site (5-star Phresh Food, Holy Cow Ice Cream, Nana's Fried Dough, The Eclectic Clam and The Lion's Club).

Notice of Erratum: In the Monday Business Edition of Soundings, the name of Lindsey Egan was spelled incorrectly. We apologize for the oversight.

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Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings


Discover Gloucester 2022 Summer Season in Review & RSVP

Thursday, October 27 | 5:30 PM

Gloucester Stage Company

Please RSVP and/or submit survey if you did not attend a roundtable session.

RUN: Effective Contract Drafting and Negotiation to Close Deals Quickly

Thursday, October 20 | 9 AM

Join Morse Law for the second of several (complimentary!) virtual sessions led by the Morse Women Attorneys Group. Each session will focus on an area of law essential to the business lifecycle, start to exit and everything in between. On Thursday, October 20, Amanda Schreyer will discuss strategies for drafting and negotiating contracts to efficiently achieve the best outcomes, while still closing deals quickly. We will approach these strategies from both sides of the table, and will look at ways to find middle ground on key terms that is acceptable to both parties. Register for Zoom link.

Gloucester 400+ Presents: A Musical Medley Fundraiser

Thursday, October 20 | 7:30 - 10:30 PM

@ Blue Lobster Company

Everybody likes to get a little Madhouse, but no one has a better time than the eight piece powerhouse rythm and blues band led by Singer Songwriter John Keegan. Put on your dancing shoes and head to Blue Collar Lobster for a light hearted night of cocktails and dancing with the band and special guests. Funds from the evening's festivities will directly support free, public programming across the city and throughout 2023! Buy Tickets Now

Fall Cider & Donut Cruises

Weekends in October

Essex River Cruises

Experience amazing Fall Foliage & Donut Cruises this month! Cruise down the river and see the leaves change into brilliant hues of yellow and orange. Enjoy complimentary hot cider and donuts from Russell Orchard of Ipswich. Book Now - Tickets are Going Fast

Rockport Music

Shalin Liu Performance Center

Mark & Maggie O'Connor: Thursday: October 20 | 8 PM

Heather Maloney: Friday, October 21 | 8 PM

Medea - Metropolitan Opera in HD: Saturday, October 22 |  12:55 PM

Della Mae: Saturday, October 22 | 8 PM

Leo Kottke: Sunday, October 23 | 7 PM

October at Hammond Castle

Spiritualism Tours by Candlelight: Thursdays in October | 7 - 9 PM

The Masquerade of Abbadia Mare: Inspired by the Tales of Edgar Allan PoeFridays in October | 6 - 9 PM

Help Clients with Healthcare Costs

Friday, October 21 | 12 - 12:30 PM

NeedyMeds Webinar

As a healthcare professional, you may often be in the difficult position of working with those struggling to meet their healthcare costs. But, you’re also in the unique position of being able to help. Join to learn the healthcare cost solutions NeedyMeds offers and how you can make a positive impact in the lives of the individuals and families you serve. Space is limited so don’t wait to sign up View All Needy Med Webinars

Scott Damgaard

Friday, October 21 | 7 - 9 PM

Whale's Jaw Cafe

Scott Damgaard was recently featured in Metronome Magazine, and has been touring the country this past year. As a songwriter, guitarist, recording artist, performing artist and producer, Scott has been constantly active making music. In addition to having written and released seven studio albums, he has also played thousands of live shows, both solo acoustic style and with a full electric band. Join us for an unforgettable evening of music from Scott, accompanied by dinner and full bar. $5 cover charge (cash or credit). Fully accessible to all and family friendly. See More Event's at Whale's Jaw Cafe

Kids Pumpkin Decorating Sail

Aboard the Schooner Thomas E. Lannon

Saturday, October 22 | 10:30 AM

Join Schooner Thomas E. Lannon for their 2nd annual pumpkin decorating sail. Includes pumpkin and materials to decorate. Purchase Tickets Today

Crossroads Wrap Party

Saturday, October 22 |  6 - 8 PM

Essex Shipbuilding Museum,  The Waterline Center

Come together to celebrate the end of "Crossroads" Essex!  The story of our small town is too big to capture in six weeks of programming. We covered as much as possible but are excited to keep exploring. Join us in continuing this conversation into the future as we learn from our past and enjoy our present! Enjoy hors d'oeuvres from the Shipyard Grille and drinks from the Basin Bar.

Cape Ann Museum Tours & Talks

CAMTalk: Exhibition Series - The Art & History of Early Photographic Processes

Saturday. OCtoer 22 | 2 - 3 PM

Hopper's Houses Walking Tour

Sunday, October 23 | 1:30 - 3 PM

The Thin Place

Through October 23

Saturdays & Sundays: Matinee: 3:00 PM

Wednesday - Saturday: Evening:7:30 PM

Gloucester Stage

Do you believe in the afterlife? Hilda does, and in her longing to reconnect with her grandmother’s spirit, she finds Linda, an esteemed medium. Linda can communicate with those in the thin place – through the veil, hearing their voices in the quiet. If you believe, she can make you hear them too. Part seance, part ghost story, this journey will make you question your assumptions about the spirit world in chilling moments of revelation. Buy Tickets

Fisheye: My Underwater Vision

A solo photography show by Dawn McDonald

Rockport Art Association & Museum

Through October 27

In an exhibition titled Fisheye: My Underwater Vision, local photographer Dawn McDonald will be taking viewers on a journey of her undersea adventures from the Pacific Ocean to the Indian Ocean, through the Sulu and Caribbean Seas, to right here in the Atlantic Ocean off Cape Ann. An avid scuba diver, McDonald’s numerous interactions with unique and endangered sea creatures, and seeing the negative changes in their environment over the years, led to her strong support for conservation and advocacy, and a desire to share the amazing beauty of the ocean and its varied inhabitants. Read More

Silent Movies with Live Keyboard Accompaniment by Jeff Rapsis

Meetinghouse Green

Sunday, October 30 | 3 - 4:30 PM

Before elaborate soundtracks and before actors spoke in films, keyboard artists entertained audiences with their live improvised musical accompaniment to follow a film's storyline. Children and adults of all ages will be delighted with the musical interpretation of keyboard artist Jeff Rapsis as he infuses new life into three works from the early era of cinematic history. Three movies to be shown are Buster Keaton's The Haunted House and Charlie Chaplin's The Floorwalker and The Kid.

Buy Tickets 

Guest Artist Matthew Billey

Showing at Seven Suns Gallery

Showing through Friday Nov 25, 2022

The “Red Sun” series and others of Matt’s paintings will be featured as a Fall Event at Loren Doucette Studio at Seven Suns Gallery.  Seven Suns Gallery is located at 48 Bearskin Neck in Rockport, Ma. and is open 7 days a week from 10:00 AM - 6:00 PM.

Read Matthew Billey's Bio

Trick or Treat & Kid's Halloween Happenings  


  • Essex: Monday, October 31 from 5 to 8 PM. Winthrop, Maple & Pickering Streets will be closed to traffic.
  • Gloucester: Starting at dusk. No official hours posted.
  • Ipswich: Monday, October 31 from 5:30 to 8:30 PM
  • Manchester-by-the-Sea: Monday, October 31 from 5:30 to 7:30 PM
  • Rockport:: Starting at dusk. No official hours posted.

Gloucester Halloween Party

Saturday, October 22

1 - 4 PM

Stage Fort Park, Gloucester

Free Admission


Wobblin Goblin Parade: Sat. Oct. 22 | 10 AM - 11:30 AM

Haunted Library: Wed., Oct. 26 | 5:30 PM - 7 PM 

Halloween Party: Mon., Oct. 31 | 5 PM - 6:30 PM  

Ipswich Downtown

Trick or Treat 

Saturday, October 29

1 - 4 PM

Downtown Ipswich

Rockport Downtown

Trick or Treat

Sunday, October 30

3 - 5 PM

Rockport Downtown Businesses

Gloucester Downtown

Trick or Treat

Monday, October 31

4 - 6 PM

Gloucester Main Street

Paid Events 

Spooky Forest Walk

Saturday, October 22 

4 - 7 PM

Doyon School, Ipswich

Buy Tickets

Trick or Treat at Hammond Castle

Thursday, October 27

3:30 - 6 PM

Hammond Castle

Buy Tickets

Hallow-Marini Party

Saturday, October 29 &

Sunday, October 30

12 - 3 PM

Marini Farm, Ipswich

Buy Tickets

Cape Ann Ongoing Events 


  • Appleton Farms: Check out all events, from Hayrides, Hikes for Beer, and Wood-Fired Pizza
  • Cape Ann Museum: Learn about all the events, exhibitions, walking tours and talks happening at CAM.
  • Essex Shipbuilding Museum: Crossroads: Change in Rural America. Smithsonian traveling exhibit highlighting changing landscape of rural America in Essex, MA open through October 22.
  • Hammond Castle: Gloucester Gratis Days every Tuesday. Self-guided tours daily.
  • Rockport Exchange: Farmer's Market every Saturday through October 15th from 9 AM to Noon in Harvey Park
  • Schooner Adventure: Weekend public sailings with free sails for children

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