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.
  Schooner Thomas E. Lannon
Last Day to Purchase 2020
Deal Coupons 
Lannon Deal Coupons will be on sale through today, Friday, December 13th. This is your last chance to pre-purchase tickets for the 2020 season. Deal Coupons are just $28 each, and you can purchase up to 5 per transaction. The Coupon entitles you to join them for any of their two-hour (non-feature) sails during our 2020 season. Click  HERE  to buy yours now. 
Within 48 hours after completing your purchase, you will receive an email at the address you provide during check–out with your coupon codes. It's very easy! If you have any questions, please contact them at
Schooner Thomas E. Lannon, 63 Rogers Street, Gloucester, MA 01930, (978) 281-6634
Main Street Shops and
Window Display Contest
Downtown, Gloucester
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 19.
Myschyffe Managed:
Medieval and Renaissance Madrigals
December 14, 2019
10:30 am - 3:00 pm  $10 – $20.00
Join them for a day of music and holiday cheer at the Hammond Castle Museum. For the first time in nearly 20 years, the holiday season is coming to Hammond Castle Museum. The halls will be decked, all will be jolly, and Myschyffe Managed will be fa la la-ing throughout the day. Myschyffe Managed sets the perfect holiday ambiance for exploring the castle while madrigals fill the air with holiday cheer. Performances times are: 10:45 a.m. to 11:30 a.m., 12:30 p.m. to 1:15 p.m., and 2:15 p.m. to 3:00 p.m. Adults are $20, Children are $10 and include self guided tours of the museum. 
Off-site parking will be provided! Please park at Stage Fort Park in Gloucester. Free shuttles will run continuously with drop offs every 15 minutes. 
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.
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
Charles Dickens'
A Christmas Carol
North Shore Music Theatre
Through December 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.
Deck The Halls
At Hammond Castle Museum
Through December 20
daily - 10am to 3:00 pm
For the first time in nearly two decades, the castle will be open to celebrate the holiday season! They have partnered with Manchester-by-the-Sea Brownie Troop 67137, All Purpose Flowers of Magnolia, Annisquam Landcare Inc., Audrey’s Flower Shop, Chapman’s Greenhouse and  Harborside Interiors who have each sponsored   a room, deck its halls and trimmed the tree. Guests can vote for their favorite room and a winner will be crowned at the end of the season. The museum will be open for self guided tours through Friday, December 20th from 10:00 am to 3:00 pm, daily. Last tickets will be sold at 2:30 pm. Ticket are: $15 Adults, $12 Seniors and $10 Children. *Please note exception: On December 14th – all tickets will be $20 as they will be hosting  Myschyffe Manage  who will perform renaissance madrigals and more throughout the day. And, the Museum is closed to the public on Sunday, December 15th for a special event.  w

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.
Back Bay Ringers at
Shalin Liu, ROCKPORT
December 15, 2019
5:00 PM
Get in the holiday spirit with the Back Bay Ringers! Back Bay Ringers (BBR) is an advanced, auditioned, handbell ensemble. Under the direction of Griff Gall, BBR has quickly developed a reputation for excellence, regularly performing at Boston-area landmarks such as Faneuil Hall, Symphony Hall, the Boston Children’s Museum, and the Prudential Center.
Tickets:$20, $15. Shalin Liu Performance Center, 37 Main St, Rockport, MA (978) 546-7391
Henri Smith
New Orleans Christmas Concert
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.
Wooden Spoon Making Workshop at Calvo Studio
December 22, 2019
9:00 Am - 5:00 Pm |
Sign up for  Calvo Wood Carving School ‘s Wooden Spoon Making full-day workshop for a wonderful opportunity to get the basic understanding of all aspects involved in learning wooden spoon carving. This is a fun class to learn how to carve a wooden spoon that you will be able to take home and use that night. Learn about the varied tools and techniques and the different woods that you can use as well as the steps how to design spoons. This full-day class includes tools for use in the class with a small fee for your materials. All you need to do is show up with your enthusiasm and have a fun time. $150.00.
Calvo Wood Carving School , 235 E Main St, Gloucester, MA. (978) 283-0231
Rockport New Year’s Eve
December 31, at 6pm -
January 1, 2020 at 12am
Ring in the New Year by taking in the sights and sounds of this interesting and diverse community event that features dozens of local shops and venues, musical events, food and other entertainment ranging from clowns and jugglers to telescope viewing with the astronomy club. The ball drops at midnight in Dock Square. The celebration begins at 6PM on Dec 3. Entertainment is scheduled on the hour, every hour. Some events are free and others require a button purchase. To participate in those events, buy a RYNE button at  participating local shops  or at the event headquarters on New Year’s Eve. www.rockportnye.or g
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
( Annisquam Light) -- 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! HAPPY HOLIDAYS TO YOU!

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