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November 23, 2022

Small Business Saturday - Shop Local

Dream House Gallery & Boutique invites you to Shop Local

4 Beach Gifts & Goodies is there 4 your Shop Local needs.

On Small Business Saturday, November 26, Shop Local, Shop Greater Cape Ann!

Greater Cape Ann Gift Checks may be purchased at the Chamber office in Gloucester, both Shaw’s locations in Gloucester, at Tuck’s Candy’s & Gifts in Rockport, and at Cape Ann Savings Bank in Manchester-by-the-Sea.

Available in any denomination from $10 - $100. Accepted at over 250 participating 

Greater Cape Ann Chamber Member businesses. Visit

to learn more.

Chamber Events

Inform, Inspire, Spark!

Tuesday, November 29 | 5 - 7PM

Register Now

Inform. Inspire. Spark! is a series of 5-minute talks sharing momentum-building work happening on greater Cape Ann in the areas of community celebrations, investment, arts and culture, decarbonization, coastal resilience, and design. 

The lightning talks will be followed by short, interactive breakout sessions where you can learn ways to get involved.

Download Flyer | Register

Coffee & Connections

Thursday, December 1

9 - 10 AM

Please join us Thursday morning, October 6 at 9 AM for our monthly virtual Coffee & Connections. This is a great opportunity for new and old members, as well as prospective members, to grab a cup of your favorite morning beverage and Zoom in from you home or office for an informal "Get to Know My Business" networking session. Know someone who would enjoy learning more about the Chamber? Please invite them to attend!

Register for Zoom Link


Mark your calendars for Friday, January 27 from 6 to 11 PM to help us celebrate 2023 President Loran Caputo and 2022 President Caitlin Pszenny, plus thank out-going and welcome incoming Board members. It promises to be a great evening of food, fun and dancing at the Beauport Hotel.

Early Registration Now Open

Tis the Season!

Gloucester Santa Parade & Tree Lighting

Sunday, November 27

End the Thanksgiving weekend with Gloucester’s Santa Parade, beginning at the State Fish Pier and ending at Kent Circle where the Tree Lighting will take place at 4:30 p.m.

The Festivities get started on Thursday, December 1 with the Manchester Division Chamber Holiday Party and Lucky 9 Drawing, where one lucky winner will have the chance to win $1,000! Tickets for the drawing cost $25 and are available for purchase at the Chamber office.

Download Brochure & Schedule

Download Window Poster

Mark your calendars for December 3. Santa wlll be arriving by lobster boat at 1 PM, followed by photos with Santa and Dock Square Tree Lighting at 4:20 PM

See Full Schedule and List of Participating Businesses on

Download Brochure & Map

Chamber Holiday Parties

Thursday, December 1 | 5 - 7 PM

Manchester Division Party and Lucky 9 Drawing @ Boo-Bird

Tuesday, December 6 | 5 - 7 PM

Rockport Division Party & Half-price Sale at Roy Moore's Fish Shack

December 7 | 5 - 7 PM

Essex Division Party @ Ripple on the Water

December 7 | 5 - 7 PM

Next Gen Party at Cape Ann Lanes

Tuesday, December 13 | 5 - 7 PM

Ipswich Division Party. Location TBD

Thursday, December 15 | 5 - 7 PM

Gloucester Chamber Party & CEO Ken Riehl's Retirement Party @ Gloucester House

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Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings

Hammond Castle Museum

Game Night: Tabletop Gaming

Thursday, November 25

4th Annual Deck the Halls

November 25 - December 30

Holiday Illumination Celebration with Jambalaya Horns

Friday, November 26 | 5:30 - 8 PM

Tree Jubilee

November 25 - 27 and December 2- 4

Marini Farm, Ipswich, MA

Over 100 Decorated Trees & Wreaths to Win! Tour the gallery of uniquely decorated trees and wreaths donated by local organizations, families, and businesses; then choose the ones you want a chance to win! OVER 100 spectacularly decorated trees and wreaths will be raffled off (decorations and all!) at the end of the Jubilee. You never know what the donors will decorate their trees with! Proceeds benefit the Ipswich Humane Group to support the animals at the Ipswich Animal Shelter.

Cape Ann Makers Market – Holiday Market

Saturday, November 26 | 11 AM - 4 PM

The Emerson Inn, Rockport

Come out to the Cape Ann Makers Market – Holiday Market at Rockport's Emerson Inn on Small Business Saturday and shop the more than 40 creative Cape Ann Artisans, Crafters and Makers!

The event will feature an incredible selection of coastal inspired and holiday themed handmade gifts, including jewelry, metalsmithing, painting, photography, fiber arts, hand harvested artisanal sea salts, natural body care and much more. Learn More & See List of Vendors

Rockport Music

Shalin Liu Performance Center

Nefesh Mountain: Saturday, November 26 | 8 PM

The Seagull - National Theatre Live: Sunday, November 27 | 1 PM

Keller Williams & Steve Poltz: Thursday, December 1 | 8 PM

A Seaside Yuletide - with Jon Butcher, Alan Estes, and Sal Baglio: Saturday, December 3 | 8 PM

Christian Tetzlaff: Sunday, December 4 | 3 PM

Adaptation Strategies for the Good Harbor Beach Ecosystem

Free Webinar from TownGreen

Wednesday, November 30 | 6:30 PM

This is the 2nd in a three-part workshop/webinar series that focuses on the Good Harbor Beach ecosystem that includes Good Harbor Beach, Salt Island, the marsh, and the surrounding connected ecosystem. Breakout Groups will allow participants to discuss the issues raised and reflect on the changes that have already happened. 

Register for Webinar

Shopping, Music & Tastings

Cellar Door | Ipswich

December 1: Sip, Shop and enjoy music by Joe and Renee Cardoza | 6 - 8 PM

December 2: Wine Tasting | 6 - 8 PM

December 9: Craft Beer Tasting | 5 - 7 PM

December 15: Live Music Shopping Night

See More Cellar Door Events in December

Discover Gloucester’s 2022 Holiday Awards Luncheon

December 1, 2022 | 12 - 1:30 PM

Cruiseport Gloucester

Join Discover Gloucester for the 2022 Holiday Awards Luncheon, first time back since 2019. The gathering is a time for colleagues and community members to celebrate the holiday season, and for Discover Gloucester to recognize individuals and organizations who have made a lasting impact in the tourism business community this year. 

Tickets are $35 per person. Registration is required. Registration and payment deadline is Friday, November 25. Learn More

Holiday Pottery Sale

Saturday, December 3 & Sunday, December 4

10 AM - 4 PM

Annisquam River Pottery & Marty Morgan Pottery

10% of all sales will go to "The Art of Lunch" Cape Ann Museum Grace Center Meals.

Download Flyer

Holiday Events

Below is a "working list" of up coming Holiday events in the greater Cape Ann region. Please visit the Community Calendar on the Chamber website for more information. For Rockport events, see dedicated Christmas in Rockport page.

Download PDF

Did we miss your event? Please email with details.

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