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December 7, 2022

Chamber Events

Amanda Armstrong Group

Office Grand Opening

Thursday, December 8 | 3 - 6 PM

35 Fuller St., Unit 100, Magnolia

Amanda Armstrong Group is delighted to announce that they are opening a satellite Compass office in Magnolia (Gloucester) to better serve their clients and provide a home base for their team on the North Shore. The Grand Opening will take place from 3pm-6pm with a ribbon-cutting ceremony to be held by the Greater Cape Ann Chamber of Commerce at 5pm. Please stop by for a tour of the space, good food and drinks, and great company. Please RSVP Here


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!

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

Chamber Holiday Parties

Wednesday, December 7 | 5 - 7 PM

Essex Division Party @ Ripple on the Water

Wednesday, December 7 | 6 - 8 PM

Next Gen Party @ Cape Ann Lanes

Please RSVP Here

Tuesday, December 13 | 5 - 7 PM

Ipswich Division Party @ American Barbecue in Rowley

Thursday, December 15 | 5:30 - 8:30 PM

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

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 9

  • 4 - 9 PM: Holiday Shopping Night with Stamp Card & Raffle
  • 9 PM: After Party & Raffle Drawing at Fleur Cuisine 

Saturday, December 10

  • 10 AM - 4 PM: Holiday Farmer’s Market at Whale Jaw Cafe
  • 1 – 3 PM: Horse-Drawn Wagon Rides; Strolling Musicians

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

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.

Winter Wreath - Making with Local Flora

Wednesday, December 7 | 5 - 6:30 PM

Backyard Growers

Learn how to design and create festive winter wreaths using local flora like amaranth, straw flower, and evergreen. Instructed by North Shore flower farmer Lauren Barnhill of Sunspell Flora, each participant will take home a wreath of their own creation. Learn More & Purchase Tickets

Rockport Music

Shalin Liu Performance Center

Handel's Messiah: Friday, December 9 | 7 PM

Metropolitan Opera Live in HD: Saturday. December 10 | 12:55 PM

Pokey LaFarge: Saturday, December 10 | 8 PM

Christmas with the Back Bay Ringers: Sunday, December 11 | 2 & 5 PM

Christmas Celtic Sojourn: Tuesday, December 13 | 4:30 & 8 PM

Eileen Ivers: Friday, December 16 | 8 PM

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

Shopping, Music & Tastings

Cellar Door | Ipswich

December 9: Craft Beer Tasting | 5 - 7 PM

December 15: Live Music Shopping Night

See More Cellar Door Events in December

Hammond Castle Museum

4th Annual Deck the Hall Guided Tours

Friday - Sunday: Through December 30 | Varying Times

Holiday Illumination Celebration

Through January 1 | 4 - 10 PM

Santa Returns to the Castle

Friday, December 16 | 3 - 6 PM

Grand Banks Makers Market

Thursday, December 8 | 2 - 7 PM

Grand Banks Showroom

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. 

Holiday Pop Up Market

at Treetop Yoga

Friday, December 9 | 6 - 8 PM

Join Treetop Yoga and Cape Ann Compass Health/Wellness Coaching for an evening to both treat yourself and treat others. Sign up for a one hour Friday Fun Yoga Flow with Sharon Esker that will include an option Hemp CBD Wellness healing from Cape Ann Compass/Green Compass. All proceeds from this $10 class will go to The Open Door.

After class, head to our lobby for shopping and meet some local wellness providers who can help you find some calm. 

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

Ipswich Jingle Bell Walk

Saturday, December 10 | 11 AM

Town Wharf & Town Hall

Santa arrive at the Town Wharf by boat at 11 AM followed by a Jingle Bell walk to Town Hall. Featuring Buddy the Elf, the Grinch, yummy food, holiday crafts, and games plus chances to win an Apple iPad and a Christmas Tree. Special guest appearance by the IHS String Quartet. The event will also feature a toy drive benefiting the Marine Toys for Tots Foundation so bring an unwrapped toy if you would like to donate.

This Community event is brought to you by the

Ipswich High School Interact Club, with the support

of the Ipswich Rotary Club. Proceeds support the charitable activities of Interact.

Download Flyer

Debut opening at the Don Gorvett Studio + Gallery

Saturday, December 10 | 3 - 7 PM

211 East Main St., Gloucester

Join us in celebrating the long-awaited opening of Don Gorvett's Studio and Gallery. We are exhibiting Don's most recent color woodcuts and drawings done since his return to Gloucester in 2019. The new work focuses on Cape Ann's maritime heritage. Enjoy seasonal light nosh and have a beverage with the artist, friends, and fellow art enthusiasts. The Don Gorvett Studio and Gallery is located upstairs at the historic Beacon Marine Basin in East Gloucester, Massachusetts. Learn More

G. F. Handel Messiah Sing

Sunday, December 11 | 11 AM

First Parish Church, Manchester by the Sea

The First Parish Church, Congregational, of Manchester-by-the-Sea is presenting its first annual Handel’s Messiah Sing. They will sing Part One and the Hallelujah Chorus. The public is invited to attend and sing these wonderful Messiah choruses! This event will be conducted by well-known composer and conductor, Dr. Herman Weiss, and will also feature professional soloists and a 14-piece orchestra.. You are encouraged to bring your own vocal score. Listeners are welcome to attend, also. A reception will be held in the Chapel Hall directly afterward. A free will offering at the door will be gratefully accepted to support future community events, but is not required to attend – all are welcome!

Pauline's Gift Shop Customer Appreciation Day

Wednesday, December 14 | 10 AM - 7 PM

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.

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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