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December 14, 2022

Chamber Events


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

Seeking Sponsors for the Annual Celebration

Promote your business during the Chamber’s most popular event of the year! If you are interested in sponsoring this evening, we have sponsorship opportunities available to businesses who wish to promote themselves to members in the community.

Download the Sponsorship Form now or contact us to learn more!


Gold Sponsors

Silver Sponsors


So Long, Farewell, auf Wiedersehen, Goodbye

Ken's Retirement Party & Chamber Holiday Party

Please join us at the Gloucester House this Thursday, December 15 from 5:30 - 7:00 PM as we celebrate the Holidays and say thank you and farewell to Ken Riehl, CEO since 2013.


It will be a very special yet bittersweet night commemorating Ken's 10 years at the helm of the Chamber. While we will "riehly" miss his tremendous leadership over this past decade, we sincerely wish him and Holly lots of "riehly" great adventures in their retirement life! They have "riehly" earned it! 


We look forward to seeing you there and lifting a glass together to honor Ken - Salut!!

ALT New Year's Eve Party

Friday, December 30 | 7 - 10 PM

Beauport Hotel

Ready to make an IMPACT in your community in 2023? Party for good at the ALT New Year's Eve Party, brought to you by a collaborative collective of Cape Ann nonprofits on December 30 at the Beauport Hotel. We're inviting the next generation of changemakers to get down to live music (The DubTones), enjoy delicious food and drink, and learn more about how you can make an impact in your own back yard in 2023. Download Flyer

Snag your tickets here:

Join Us for the First Coffee & Connections of 2023!

Thursday, January 5 | 9 AM

This will be the first Coffee & Connections for new CEO Steve Buckley, so please join us in welcoming him to this fun morning networking event!

Please join us on the first Thursday of the month at 9 AM for our virtual Coffee & Connections. For new & prospective members, this is the perfect opportunity to introduce your business and meet other members and Chamber staff. For veteran members, it is a great way to let new members learn about your business and talk about anything new and exciting in the works for you. So grab a cup of your favorite morning beverage and Zoom in from your home or office for an informal "Get to Know My Business" networking session. Also, if you know someone who would enjoy learning more about the Chamber, please invite them to attend!

Improv & Martinis

Wednesday, January 18 | 6:30 PM

A Great Gathering at The Fish Shack

$45 per person

(Rescheduled from November 2)

Start the New Year off with Improv & Martini’s, a Great Gathering of Total Delight led by Izzy Gesell. Izzy is a Professional Humorist, Improv Master, Organizational Alchemist. Join us for an evening full of Engaging Fun, Fantastic Food, and Amazing Adult Beverages. No need to go to New York, or L.A. or Boston because the hot spot of the universe will be right here, in Rockport, Massachusetts! 

A limited number of tickets are available so Register Now to Reserve Your Ticket!

Shop Local - Shop Greater Cape Ann

Essex Evening Holiday Shop Hop

Thursday, December 15 | 4 - 8 PM

With 14 Participating Retail Stores and 18 Restaurants & Markets

Download Map

46th Annual Men's Night (All Day) Gloucester Shopping Night

Thursday, December 15

10 AM - 8 PM

 Men’s Night is a special evening geared towards men’s shopping needs in Gloucester. Come enjoy the festive decorations and friendly service of local merchants. Men’s night will feature events including raffles, gift certificates, special promotions, extended holiday hours, and refreshments.

Christmas in Rockport: Weekend Schedule at a Glance

Friday, December 16 - Sunday, December 18

  • Last Minute Stocking Stuffer Weekend

Saturday, December 17

  • 2:30 PM: Christmas Concert at the Rockport Baptist Church
  • 5 PM: Live Nativity Reenactment Pageant

Sunday, December 18

  • 4:30 PM: Menorah Lighting & Chanukah Celebration at Bartlett Park

View Full Schedule

Give the Gift of 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.

Visit Our Premium Advertiser

Member & Community Events

Please Check the Full Community Calendar for All Member Event Listings

See Holiday Events at End of Newsletter for a Detailed List of Upcoming Holiday Events

Pauline's Gift Shop Customer Appreciation Day

Wednesday, December 14 | 10 AM - 7 PM

Hammond Castle Museum

Santa Returns to the Castle

Friday, December 16 | 3 - 6 PM

4th Annual Deck the Hall Guided Tours

Friday - Sunday: Through December 30 | Varying Times

Holiday Illumination Celebration

Through January 1 | 4 - 10 PM

Rockport Music

Shalin Liu Performance Center

Eileen Ivers: Friday, December 16 | 8 PM

Cape Ann Big Band Holiday: Saturday, December 17 | 2 & 7 PM

John Pizzarelli Trio: Sunday, December 18 | 5 PM

Sawyer Free Library @ 21 Main Street Open House

Saturday, December 17 | 10 AM - 2 PM

Come discover the Sawyer Free Library's new space and learn about all its services, both in person and digital. Swing by to say hello to your favorite librarians and meet a few new ones. There will be a scavenger hunt for kids, local history display and more for all to enjoy. Cookies and hot chocolate will be served too!

Cape Ann Makers Market - Last Chance Holiday Market

Saturday, December 17 | 11 AM - 3 PM

West Gloucester Trinitarian Congregational Church

Cape Ann Makers Market featuring 13 vendors specifically chosen for the giftability of their products! Everything from candles, soaps, body care, sea salts, jewelry, handcrafted bags, pottery, photography and more! All handcrafted by local artisans. Get your last minute shopping done or buy yourself something nice for the New Year.

American Originals: A Moravian Christmas

December 17 | 7:30 PM

Gloucester Meetinghouse.

The Musicians of the Old Post Road perform chamber music from the Moravian community played on period instruments.Musical selections are drawn from Moravian composers including several modern-day premieres of works penned by America’s Moravian immigrants along with selections by Johann Joachim Quantz, Carl Heinrich Graun, and Johann Christoph Friedrich Bach, the fifth son of J.S. Bach. Buy Tickets

A Big Band Holiday

December 18 | 7:30 PM

Gloucester Meetinghouse.

The Gloucester Meetinghouse Foundation welcomes the Cape Ann Big Band and guest vocalists in a magical evening of holiday music at the Gloucester Meetinghouse at the corner of Middle and Church Streets.

Buy Tickets

Chanukah Celebration

Ipswich Public Menorah Lighting

Tuesday, December 20 | 5:30 - 7:30 PM

Town Hill & Gathr

The Public Menorah celebrates Jewish tradition, culture, and pride. Celebrate with us, as we light the giant menorah and celebrate Chanukah with friends, family, and community leaders. Enjoy festive music, jelly donuts, latkes, chocolate gelt, and great Chanukah spirit! Menorah Lighting will be at the bottom of Town Hill. Chanukah Celebration will follow at Gathr - 42 Market Street, Ipswich, MA 01938

Christmas at Castle Hill

Fridays, Saturdays, Sundays through December 31

Castle Hill, Ipswich MA

Grand Banks is hosting it's first Makers Market. They will be featuring 8 local vendors who have mastered their crafts. In our Germany inspired Bier Garten Penny Packers food truck will be serving up a variety of savory dishes while Alexis from Helen's Bottle Shop keeps us warm with thoughtfully selected choices of wine, beer, and festive mocktails. Christmas at Castle Hill runs Fridays, December 2, 9, and 16, 5-8PM; Saturdays, December 3, 10, and 17, 10AM-4PM; Sundays, December 4, 11, and 18, 10AM-4PM; and December 27-31, 10AM-4PM.

Make Reservations

Masterpieces in Miniature

Daily through December 31

Rockport Art Association & Museum

Stop by Rockport Art Association & Museum for small works of art created by juried artist members for sale. Art makes a great holiday gift.

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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