The Holidays in Gloucester – Enjoy Holiday Cheer During your Cape Ann Visit

December 07, 2020 / Art and Music, Good to Know, Outdoor Adventures, Things to Do & See

The holiday season is looking a bit different this year, but Gloucester and Cape Ann are as cheerful as ever.

Be sure to visit the Beauport Hotel Gloucester lobby to find the holiday spirit. Their annual holiday décor is designed and installed by Meredith McCarthy Floral Design and Event Styling each year, combining the holiday season with Beauport’s classic style. Covered in cheer and filled with festive garlands, wreaths, trees and more, you are sure to feel the holiday spirit during your Beauport stay or dining experience at 1606 Restaurant and Bar. While you’re there, visit the Beauport Boutique and shop for the whole family. Find lines from Colby Davis of Boston Jewelry, Mariposa, Vineyard Vines, Rockport Candle Company and more. There is a gift for everyone!

Another local must-see is the Hammond Castle Museum, which will be decorated by small businesses throughout the holidays. Santa will be visiting the museum on December 10 and 11. But be sure to call ahead if you want to stop by the museum on Fridays, Saturdays and Sunday in December for guided tours. Tours are ticketed and timed to keep everyone safe and by reservation only. Learn more HERE.

Maritime Gloucester is celebrating the holidays with “Deck the Docks” with a virtual twist! The annual collaboration with SeArts gives the opportunity for artists to showcase their work for your viewing from the comfort of your own home. Shop the artists’ work and learn more HERE. Maritime Gloucester is also selling Christmas trees and participating in the First Annual Winter Lights on Cape Ann celebration. You’ll also get a chance to see the schooners Adventure and Ardelle lit up in their finest festive spirit of sparkles!

We encourage you to check out the North Shore Art Associations’ new Holiday Sale of Fine Art, now live HERE. Their Holiday Sale of Fine Art is Now Live! This eclectic collection of NSAA members work is on view and available for purchase. Here you can find the perfect gift – or treat yourself!Art makes a truly meaningful gift, AND your purchase helps support local artists and the North Shore Arts Association. Visit the holiday collection HERE.

A classic Gloucester holiday spot is found next to the police station on Main Street, the Lobster Trap Christmas Tree. This handmade tree is unique to Cape Ann and a must see this season. While finding yourself downtown, be sure to enjoy the Holiday Shopping Spree. Shopping small and local in Gloucester throughout December is encouraged and be sure you enter the Holiday Shopping Spree contest. At participating stores, they will provide you with a ticket to fill out and enter to win a gift certificate curated from the Shop Gloucester, Gloucester Downtown Association. So many reasons to shop local here in Gloucester!

Take a drive into Rockport and enjoy all kinds of new holiday happenings. The 75th Annual Christmas Pageant will be a window exhibition in shops downtown with costumes designed by the Rockport Art Association & Museum. Each display will feature a QR code to the RAAM website to learn more about the annual pageant (virtual this year). Learn more HERE.

Local artists have come together for the Holiday Tree Art Stroll in Rockport. Which will feature wooden trees designed by Rusty Kinnunen of Rusty & Ingrid Creative Company, prepared by Pete Willcox and his team from the Rockport Rotary Club and painted by local artists. Each tree will be placed in the Rockport Cultural District creating a unique walking art stroll to enjoy with your family and friends.

The Sammy the Seagull Hide & Seek Game will challenge kids to find Sammy decked out in holiday cheer all over town and find a secret message by using their decoder sheet. Once completed, they can visit Brother’s Brew, Tuck’s Candy Factory, the Fudgery, and Happy Whale for free, fun holiday treats. While looking for Sammy and find yourself downtown on Friday and Saturday nights until 8pm, enjoy festive holiday strolls, complete with specials at the restaurants and cafes. Looking to reach Santa while you’re here? Head over to the North Pole Post Office and write him a personal letter. Try to spot some of his elves working in the mailroom. Bearskin Neck and Downtown are also participating in the First Annual Winter Lights on Cape Ann – be sure to take a stroll/or drive through this magical land of wonderful gifts, treats, displays and joy!

Wrap up a holiday evening and hop in the car for a scenic cruise for the First Annual Winter Lights Display on Cape Ann. Throughout Gloucester, Rockport, Essex and Manchester, over 150 locations are lit up for the holiday season for you to enjoy while social distancing. Pop on your favorite holiday playlist, maybe stop along the way for hot cocoa, and enjoy the ride. We also encourage you to check out the downloadable brochure and custom designed Google Map here, designed to provide an easy, enjoyable evening of lights, celebration, shopping, dining, — and perhaps an overnight stay too! Learn more HERE