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October 12, 2022

Business After Hours at Appleton Farms 

Drone View courtesy Jurek Schreiner, Look of Joy Photography

Chamber Events

$25K Game $$ WIN BIG $$

Thursday, October 20 | 5 - 7 PM

Gloucester Elks


Join us at the Gloucester Elks for the Big Game Drawing! There is limited seating available, so please Reserve Your Spot Today!

Tickets are available for purchase at the Chamber office. There are 12 chances to win with a total of $25,000 being given away. Cost is $100 per ticket, with a limit of 500 tickets being sold. 


  Grand Prize: $10,000

  Second Prize: $5,000

  Third Prize: $2,500

  Fourth Prize (6): $1,000

  Fifth Prize (3): $500


In addition, 50/50 Raffle tickets are also available for purchase. A Body Length is $20 and an Arm Length is $10.

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).

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Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings

Ipswich Illumination

October 14 - 16

Illumination, now in its 13th year, features a collection of interactive art installations, live music, poetry, projection, bonfires and more along the Ipswich River. Admission for all events is free, pay as you go for food and drinks.

Illumination kicks off Friday evening with a screening of "A Beautiful Day in the Neighborhood" at the Take Out Terrace. Saturday is packed full of events, music and food, including bonfire lighting by archery. Illumination wraps up on Sunday afternoon with poetry and swing dancing.

See Full Schedule

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

Absolute Jack Flies Again: National Theatre in HD, Thursday, October 13 | 7 PM

From A. to Beatles: Sunday, October 16 | 7 PM

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

Heather Maloney: Friday, October 21 | 8 PM

Guest Artist Matthew Billey

Showing at Seven Suns Gallery

Artist Reception: Friday, October 14 | 5 - 8 PM

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

October at Hammond Castle

Nosferatu: A Symphony of Horror with Live Accompaniment by Peter KrasinskiWednesday, October 12 | 7 - 9 PM

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

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

RemediChain: A New Kind of Medication Reclamation Program Webinar

Thursday, October 13 | 4 - 4:30 PM

Needy Meds

Join this 30-minute webinar to be introduced to RemediChain, a platform that allows individuals to donate unused medications to patients in need. Using the platform when disposing of unused, unneeded medications will allow you to help someone in need, reduce medicinal waste, and protect the environment. During the presentation, you'll learn how to donate medications, register as a patient in need, and view the real-time inventory of available medications. View All Needy Med Webinars

Open Mic Night

Friday, October 14 | 7 - 9 PM

Whale's Jaw Cafe

Open Mic Night is back with host John Hicks! Full bar and dinner available throughout the night. Call us to reserve your table, 978-999-5241. Located at entrance of Whistlestop Mall. Plentiful free parking and fully accessible to all abilities. $5 cover charge per person (cash or credit). See More Event's at Whale's Jaw Cafe

Elevate 2022 Woman's Conference

Saturday, October 15 | 8 AM - 2 PM

Endicott College

Elevate 2022 is brought you by the Colin & Erika Angle Center for Entrepreneurship at Endicott College and is focused on developing the next generation of entrepreneurs across all sectors of business. Take part is sessions led by those who have founded successful companies along with rounding out your skills in all things entrepreneurial.

Free for students and faculty. Sign Up Now

Wedding Giveaway & Venue Tour Open House

Saturday, October 15 | 12 - 4 PM

Cape Ann Cruises @ Gloucester House Dock

With partners Cake Ann, All Purpose Flowers & Gloucester House

Come Tour the yacht F/V Wejack (dockside) to learn how your wedding, event, and celebration could be experienced cruising aboard a yacht with your guests. Open house features stationed hors d'ouevres, complimentary mimosas, table display set-ups, meet Captain and wedding coordinator, wedding cake display, and more! (Rain date Sunday, October 16)

Register for Open House and/or Your Chance to Win a Wedding!

Cape Ann Museum Tours & Talks

Hopper Houses Walking Tour: Saturday, October 8 | 10:30 AM - 12 PM

CAMTalk: History Series -- Fictive Kin: Re-visiting the Relations of Frank Speck and His Indigenous Interlocutors: Saturday, October 15 | 2 - 3PM

Joe Garland's Gloucester Walking Tour: Sunday, October 16 | 1:30 - 3 PM

Castle Hill Vintage Car Hill Climb

Sunday, October 16 | 9 AM - 4 PM

Crane Estate at Castle Hill, Ipswich

Join The Trustees and the Vintage Sports Car Club of America for an exciting new event featuring pre-WWII cars competing in times races. Come for the day and enjoy live music, food trucks, a bootlegger’s garden and picnicking on the lawn! Schedule a 30-minute guided Great House tour set in 1929. A Crane maid or footman will show you guest and family rooms. Advance tour reservations and additional fee are required. Cars will race in the morning and again in the afternoon with a midday lunch break when the autos will be on display in the Great House forecourt. Designated viewing spots will allow spectators to safely watch the races. Learn More & Buy Tickets

Nervous Theatre’s production of Samuel Beckett’s TEXTS FOR NOTHING

Sunday, October 16 | 7:30 - 9:30 PM

Tuesday, October 18 | 7:30 - 9:30 PM

Gloucester Stage

Be immersed in the words of Samuel Beckett as audiences of only 30 gather around a single performer murmuring into the darkness. Texts For Nothing plumbs the depths of isolation and dread in this stark meditation on the nature of being. 

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

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

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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