Planning a Holiday Getaway? We've got lots of Reasons to celebrate the Season here in Gloucester. Cape Ann is chock full of events that will make your heart sing and your soul rejoice. Festivals, Decorated Window Contest, Fireside Dining, Live Music, Warm Hospitality, Great Shopping and Art Exhibits! Joy is all around! Be Part of It.
Cape Ann Makers Market
Saturday, November 30,
9:00 AM - 4:00 PM
Cape Ann Auction House,
1 Kondelin Road, Gloucester
Cape Ann Makers Market (CAMM) is excited to present  2019 Holiday Market, our first semi curated holiday market experience on November 30, 2019. The Holiday Market will be an indoor holiday shopping event featuring over 30 artisans, crafters, and makers of Cape Ann and beyond. 
Cape Ann Makers Market (CAMM) is dedicated to celebrating our makers, from Gloucester, Essex, Manchester-by-the-Sea and Rockport, who strive to create and sell high quality handcrafted goods such as jewelry, ceramics, printing, painting, photography, woodworking, fiber arts, and more. We believe in a creative collective approach. It’s our goal to promote collective local shopping alternatives, with a unique atmosphere to support our local makers, local environment, and local economy. Visit them on FaceBook CAMakerMarket
Sunday, December 1
@ 3:00 - 5:00 pm

Welcome the Christmas holiday to Gloucester at the annual Christmas Parade, the official start of the Holiday Season on Cape Ann! The Annual Christmas Parade starts at 3pm and winds it's way through downtown Gloucester to Stacey Boulevard and Kent Circle , for the lighting of the Tree ceremony which begins at about 4:15pm. Santa will be there to Welcome Everyone! Stay tuned for more details on the festivities. 
Handel's Messiah
The Handel & Haydn Society
Monday, December 2, @ 7 PM
First Congregational Church of Rockport, across from
Shalin Liu Performance Center
Handel’s iconic Messiah is a treasured holiday tradition that will be performed by the incomparable Handel & Haydn Society in a special chamber arrangement for 13-member chamber orchestra and chorus led by Associate Conductor Ian Watson. The Yankee Magazine hails that “The Handel and Haydn Society’s Messiah remains unmatched.”  This concert will be held at the First Congregational Church of Rockport  (across the street from the Shalin Liu Performance Center).
Meet The Artist Night:
Marion Rayner,
December 2, 2019
Hammond Castle Museum
Marion Rayner is an experienced watercolor artist whose inspiration comes from the natural beauty that surrounds Cape Ann. She is particularly fond of the landscapes, seascapes and scenes around her home. The opening reception will be from 5:30 to 7:30 pm and Rayner’s show will be available in our Museum Shop through the month of December. Opening reception tickets are free and may be reserved at:
Life Bloom Massage & Spa,
Holiday Sales Event
Buy one, get one 25% off gift certificates for the whole
month of December. (Limit 4 per person).   LifeBloom Holiday Sale Event. A ONE DAY ONLY event on Saturday, December 7th from 10am-8pm all gift certificates are buy one, get one 50%off. Join us for hot cocoa, holiday cookies, and festive shopping!  Life Bloom Massage & Spa, 5C Dr. Osman Babson Road, Gloucester, 978-559-7896.
Main Street Shops and
Window Display Contest
Downtown, Gloucester
Beginning Nov. 29
It's beginning to look at lot like Christmas! Main Street in Downtown Gloucester will be twinkling and sparkling with extra holiday cheer! That’s because a number of businesses are participating in the  Downtown Gloucester Holiday Window Contest ! Stroll down Main Street to look at all of the beautifully decorated windows and vote for your favorite winner in 5 different categories. Window Winners announced on December 20.
Thurs., December 5
5:00 pm - 10:00 pm

Head to Downtown Gloucester on Thursday, December 5th, 2019 for the 46th Annual Ladies Night. Enjoy refreshments, discounts, and a fun shopping event. Click HERE for more information. Free Fun For All!
Harborview Inn
Holiday Gift Certificates!
$300 to spend at the Harborview for $269. 
$200 to spend at the Harborview for $169. 
$150 to spend at the Harborview for $129. 
Call 1-978-283-2277 to purchase your gift certificates.

Two Night Discount
Stay 2 nights, receive a discount!
Reserve 2 nights: receive the second night at half price! 
Valid beginning November 1, 2019 for stays Sunday – Thursday, thru March 31, 2019 
Special not valid if booked via third-party booking site (,, Expedia. etc.).  Mention this special when making your reservation at  or when calling 1-978-283-227
Boxwood Tree Design Class
Beauport Hotel Gloucester
55 Commercial Street
Thurs., December 5
​@ 7:00 - 9:30 PM

Join us on Thursday, December 5th, for a Boxwood Tree Design class co-hosted by Beauport Hotel Gloucester and Audrey's Flower Shop. It's a great way to mingle, meet new people, and prepare for the holiday season as you design and arrange your own Boxwood Tree. Cocktail service and bar bites menu will be available during the event as well.
All materials are included with your ticket.
Tickets are $80 and can be purchased by visiting this link: and click on FLORAL DESIGN CLASSES
For more information, call Audrey's Flower Shop at 978-283-2171
December 6-8
From December 6th through December 8th, Maritime Gloucester is hosting Deck the Docks, a holiday open house, featuring a pop-up art gallery, crafts, trees, wreaths, great gifts ideas. A fun day for family and friends to enjoy a little of everything to brighten the days and lighten the holiday stress! Click HERE for more info.
Charles Dickens'
A Christmas Carol
North Shore Music Theatre
December 6 - 22, 2019
New England’s brightest holiday tradition! An original adaptation based on Charles Dickens’ classic novella, A CHRISTMAS CAROL is a musical ghost story following the miserly Ebenezer Scrooge through a series of strange and magical journeys, where he ultimately discovers the true spirit of the holiday season. Featuring dazzling special effects and traditional songs like “God Rest Ye Merry Gentleman,” “The Boar's Head Carol,” and “We Wish You A Merry Christmas,” this award-winning production was created specifically for North Shore Music Theatre and has been seen by more than one million people since its debut in 1989.
Santa's Arrival by Boat - Rockport
Sat., December 7, 2019
1:00 - 3:30 PM
Where else can you see Santa arrive by lobster boat? Santa will arrive at Rockport’s T-Wharf on Rockport Harbor on Saturday, December 7, 2019 at 1:00 PM, following a brisk lobster boat ride across Sandy Bay. Then Santa will climb up onto a Rockport Forest Fire truck and proceed along T-Wharf and across the street to Rockport Baptist Church led by Rockport cub scouts. This year Santa will be able to linger a while to visit and have photos taken with the children at the church until the Tree Lighting Ceremony begins. Then Santa will head over to Dock Square to greet the crowd and kick off the Tree Lighting festivities, before climbing back onto the fire truck to begin his long return journey to the North Pole.
Annisquam Christmast Fair
Saturday, December 7
@ 8:00 Am - 12:00 PM
The Annisquam Christmas Fair features handmade holiday greens, centerpieces, wreaths and plants, exceptional handmade crafts and a glittering display of costume jewelry. Beautifully wrapped foods, baked goods and preserves are all prepared by Circle members, and there is even something for a beloved pet! Free.
Hammond Castle Museum
Holiday Craft Fair
Saturday, December 7
@ 10:00 am - 2:00 pm  
Join us for a Holiday Craft Fair to kick off the start of the holiday season at Hammond Castle Museum! Shop locally made products from around Cape Ann and take self guided tours of the museum! Our craft fair will include over 10 vendors and artisans and the museum will be decorated for the holiday season. Advanced tickets are available. Scroll down to purchased your tickets today!
Sunday, December 8
11am or 2pm
Cruise Port Gloucester 

Enjoy a harbor cruise aboard the luxurious Beauport Cruiselines! We will be singing holiday carols with the elves, enjoying hot cocoa and cookies, and listen to a reading of “The Night Before Christmas.” Plus a visit from Santa himself! Tickets include hot cocoa, cookies, and a picture with Santa. Beauport Cruise Lines, 6 Rowe Square, Gloucester. Get tickets at: www.beauportcruisesline
Saturday, December 14
10:00 am - 4:30 pm
  Join  us for the 31st annual Middle Street Walk! Be enchanted by historic Middle Street in the winter season. Performances, crafting, contests, trolley tours and more! Details at  www. .
 The Cape Ann Museum is free and open to the public all day!
Sat., December 14 @ 4:30 pm
Main Street, Gloucester, MA 
Gather together on Main Street for Gloucester's Lobster Trap Tree Lighting on December 14th starting at 4:30 pm. It's a fun, family activity! Lobster Traps and Lobster Buoys, decorated by the children of Cape Ann Art Haven, make up this distinctly unique Christmas Tree in downtown Gloucester.
Rockport Makers' Festival
Town of Rockport
Weekend of
December 14-15, 2019
Come to the Rockport Makers' Festival for an unforgettable holiday experience on December 15th and 16th! Shop for the perfect handmade gifts in a seaside Christmas village. Plus, shop some of New England's best creative brands at the Holiday Market in two locations: Rockport Art Association & Museum and Brackett's Ocean View Restaurant. Join in on the fun at the town-wide celebration of Rockport's creative businesses with maker-themed events in the shops, festive food, music, and attractions at Rockport's famous art venue. Click HERE for more info.
Henri Smith
New Orleans Christmas
Sat., December 21 
at 8pm
Gloucester Stage Company

Featuring Grammy-winner Amadee Castenell New Orleans Singer/Bandleader Henri Smith brings his 9-piece band back to the Gloucester Stage Company for a special New Orleans Christmas concert after their sold-out Gloucester Concert Series premiere last May.
Rockport’s Live
Christmas Pageant
Dock Square and Main Street
Saturday, December 21
5 pm. A torch-lit live
re-enactment of the Nativity.

I n the spirit of the holidays, the Rockport Art Association and Museum once again presents the Annual Live Christmas Pageant. The pageant will be held Saturday, December 21 at 5PM (rain date Sunday, December 22 at 5PM).
Each year hundreds of spectators gather to watch the live re-enactment of the story of baby Jesus, Mary and Joseph, the Bethlehem inn and the stable. The pageant begins with a torch lit procession which starts at Dock Square and proceeds up Main Street to the Congregational Church. Here the story of Jesus’ birth is brought to life through a live narration.
All that Sparkles!
We recommend that you take a walk, grab the kids for a car ride or take a stroll along the Harbor to view some magnificent holiday lights in and around Gloucester and Cape Ann. From the store fronts on Main Street, to the Boulevard, to the working waterfront on Rogers Street, to the Back Shore and through the woods, you'll enjoy festive lights, welcoming motels and inns, fireside dining, and so much more. We encourage you to visit Gloucester and celebrate the season of hope, joy and enchantment. We are blessed with a city that is full of love. We wish you a most beautiful holiday season with friends and family and look forward to seeing you soon
-- we'll be sure to leave the light on!
Stay tuned for more Upcoming Events!
Be sure to click on
for more of what to do in Gloucester, Cape Ann!

Elizabeth Carey
Executive Director
Discover Gloucester
PO Box 915
Gloucester, MA 01930
and keep a toe in the sand