Gloucester Christmas Events & Things to Do 2025

Step back in time at the Middle Street Walk, a cherished holiday tradition. Explore historic churches and buildings, browse local crafts, and enjoy festive food. Highlights include a Gingerbread House Contest, live music, horse-drawn hay rides, and a unique Lobster Trap Tree lighting ceremony. It's a day of community, history,...

Discover the charm of the Cape Ann Makers Holiday Market, a premier event celebrating local artisans. Browse a curated selection of high-quality, handmade goods, original designs, and unique crafts created by talented makers from Gloucester and surrounding towns. It's the perfect opportunity to find distinctive holiday gifts while supporting the...

Experience the charm of the Annisquam Sewing Circle Christmas Fair, a beloved annual event. Members meticulously craft unique gifts, ornaments, and festive treats throughout the year, offering a delightful shopping experience. This community gathering is held at the historic Annisquam Village Hall, creating a warm and inviting atmosphere for all...

Rockport transforms into a winter wonderland throughout December with 'Christmas in Rockport.' Festivities include Santa's grand arrival by boat, a magical tree lighting ceremony, and a live Nativity pageant. Explore unique shops during Mistletoe Madness and Stocking Stuffer Weekend, enjoy festive music from carolers and strolling musicians, and take a...

Discover the warmth of the holiday season at the 54th Annual Marblehead Christmas Walk. This signature New England event transforms the historic town into an enchanting winter wonderland. Enjoy a festive weekend featuring preview shopping, a tree lighting ceremony, Santa's unique arrival by lobster boat, a vibrant parade, an artisan...

Salem's So Sweet is a beloved annual festival celebrating chocolate and ice sculptures. Visitors can explore dazzling ice creations throughout town, enjoy sweet treats and special deals from local businesses, and participate in the fun Chocolate Hearts Challenge game. The event kicks off with a festive party and late-night shopping.

Experience the best of New England's culinary and artisanal talent at the Craft & Specialty Food Fair. This three-day event in Topsfield showcases a vibrant marketplace brimming with exquisite handmade crafts and delectable specialty foods. Discover unique gourmet treats, watch live demonstrations, and savor the flavors of local food innovators.

Discover unique, handmade treasures at the Peabody Institute Library's third annual Winter Arts & Crafts Fair. This vibrant market, held during the Peabody Main Streets Holiday Stroll, features local artists showcasing their crafts. Find the perfect gift for any winter holiday celebration while supporting local creators and enjoying a festive...

Experience the charm of the Saint Joseph School Annual Christmas Craft Fair, a cherished tradition spanning over 40 years. This festive event offers a delightful array of handmade crafts, personalized ornaments, and seasonal decor. Browse unique items, try your luck with exciting raffles and a silent auction, and enjoy delicious...

Discover a festive indoor Holiday Market at the Melrose Family YMCA, offering a wonderful opportunity to find unique holiday gifts and delicious seasonal foods. This event brings together local artisans and producers, providing a charming atmosphere to get into the holiday spirit and support the community.

Step back in time at the Dickens Holiday Marketplace and Craft Fair, a festive event transforming the RMHS Main Street hallway into a winter wonderland. Discover unique treasures from over 50 artisan vendors, enjoy the sounds of strolling carolers and live musical performances, and immerse yourself in the holiday spirit...

Step into the holiday spirit with North Shore Music Theatre's 35th anniversary production of 'A Christmas Carol.' This beloved musical ghost story follows Ebenezer Scrooge on a transformative journey, featuring dazzling special effects and traditional carols. It's a timeless tale of redemption and the true meaning of the season, perfect...

Get ready for a joyous and raucous holiday celebration as the Squirrel Nut Zippers bring their Christmas Caravan Tour to town. They deliver a unique musical experience, blending festive hits with their signature sound inspired by early 20th-century jazz and folk music. Prepare for an unforgettable night that captures the...

Step aboard the Salem Trolley for a unique and interactive performance of Charles Dickens' 'A Christmas Carol.' This beloved holiday classic is brought to life in a humorous and whimsical way, offering a completely unexpected experience as you ride along with Scrooge. Now in its 39th season, this show sells...

Experience one of Melrose's most beloved holiday traditions with the Melrose Symphony's Holiday Pops. Joined by vocalist Renese King and her band, they present a magical evening filled with holiday classics, sparkling arrangements, and opportunities for joyful sing-alongs. Get into the festive spirit with this enchanting musical event.

Experience the magic of the holiday season with a Candlelight concert at the Simons Theatre. This special event features a captivating performance of Tchaikovsky's "The Nutcracker" suite, alongside beloved holiday classics like "O Holy Night" and "Greensleeves." Let the enchanting melodies and the warm glow of candlelight transport you into...

Prepare for an unforgettable evening with the world-renowned tenor, Andrea Bocelli, as he graces the stage at TD Garden. Bocelli will perform a captivating selection of music, including cherished holiday songs from his chart-topping album 'A Family Christmas,' alongside his most beloved arias and crossover hits. This concert promises an...

Boston Ballet presents Mikko Nissinen's The Nutcracker, a breathtaking holiday spectacle. Journey with Clara on Christmas Eve through a magical world filled with dancing bears, a growing Christmas tree, and an epic battle with the Mouse King. This production features technically challenging choreography, stunning sets and costumes, and the enchanting...

Discover the magic of 'Midwinter Revels: A Scandinavian Story for Christmas,' a cherished holiday tradition. This captivating production weaves together festive Scandinavian songs and dances with an enchanting story inspired by Gregory Maguire's 'Matchless.' Experience the warmth and light of a tale set on a northern island, brought to life...

Experience the magic of the season with the Boston Pops' renowned Holiday Pops concert. This beloved annual tradition brings festive cheer to Symphony Hall with beloved holiday classics. Conducted by Keith Lockhart and featuring the Tanglewood Festival Chorus, the performance promises an unforgettable celebration of holiday spirit.

Step back in time this holiday season at Hammond Castle Museum's 7th annual 'Deck The Halls' celebration. Explore rooms transformed with festive trees, twinkling lights, and elegant décor, each with a unique holiday theme. Discover playful elves, nutcracker guards, and even menorahs honoring Hanukkah. For an extra magical experience, join...

Immerse yourself in a holiday wonderland by the sea at the Sea Festival of Trees. This beloved tradition showcases thousands of glittering Christmas trees, offers seaside indoor ice skating, and features visits from Santa and popular characters. It's a festive celebration supporting the historic Salisbury Beach Carousel.

Step into a dazzling winter wonderland at Stone Zoo's ZooLights, where thousands of twinkling lights transform the zoo into a magical holiday spectacle. Wander through tree-lined paths adorned with festive displays and catch glimpses of resident animals like flamingos, black bears, and reindeer. This enchanting event offers a unique opportunity...

Experience the Merrimack Valley Celebration of Lights, a spectacular drive-through event showcasing over a mile of dazzling displays. Featuring more than 1 million LED lights, this attraction boasts the longest light tunnel in New England, offering a magical journey through a winter wonderland from the comfort of your vehicle.

Step into a world of wonder at SOLSTICE: Reflections on Winter Light, an annual event transforming Mount Auburn Cemetery into an illuminated wonderland. Wander through captivating outdoor light and sound artworks, and find a moment of peace indoors with live music and candle lighting. It's a perfect opportunity to reflect...

Join the Greater Cape Ann Chamber of Commerce staff for their annual holiday celebration. This festive gathering offers a relaxed opportunity to connect with fellow business professionals and community members. It's a perfect chance to mingle, share holiday cheer, and wish everyone a happy holiday season.

Ring in the New Year with a spectacular celebration at the Doubletree Hilton Danvers. This 'Hoppin' New Year's Eve Party' promises an unforgettable night filled with music, dancing, and festive cheer. Guests can expect a delightful dining experience and a vibrant atmosphere to welcome the upcoming year in style.

Step back in time at the Holiday Open House hosted by the Sandy Bay Historical Society. This special event invites visitors to explore the beautifully preserved Sewall-Scripture House, a historic gem built in 1832. Discover fascinating local history, genealogical records, and unique artifacts that tell the story of Rockport.

Experience the magic of Christmas as Santa arrives by boat at Masconomo Park for the annual Christmas-by-the-Sea event. Children can join Santa for a Jingle Bell Walk and parade, followed by opportunities for photos. The afternoon also features crafts, face painting, a candy cane hunt, and refreshments, with a special...

Craft a unique holiday tree adorned with genuine sea glass at this festive workshop. Participants will receive wine, snacks, and desserts, with a cash bar available for additional beverages. It's a perfect opportunity to blend holiday cheer with coastal charm.

Get ready for the 4th annual Downtown Salem Holiday Parade! This family-friendly event brings holiday magic to the heart of downtown with dozens of colorful floats, festive characters, and live musical performances. The parade culminates in a joyous tree lighting ceremony, creating a truly magical experience for all.

Experience the magic of the 9th Annual Peabody Holiday Stroll, a festive community celebration across downtown Peabody. Enjoy a day filled with Reindeer Games, Santa's Workshop, and creative craft activities. Witness live music, dance performances, and a special 'Touch a Truck' event. The festivities conclude with caroling and a tree...

Join the Wakefield Center Neighborhood Association for their annual Lighting of the Lights ceremony. This beloved community event marks the start of the holiday season with the ceremonial illumination of the Upper Common. Attendees can enjoy complimentary hot chocolate and a heartwarming choir performance, with a special appearance by a...

Get ready for the Stoneham Holiday Parade, an annual celebration that brings the community together. This festive event features a rolling parade with decorated floats and participants from local businesses and organizations, all designed to spread holiday cheer throughout the town. It's a wonderful opportunity to experience the festive spirit...

Embark on a magical journey aboard the North Pole Express, a festive train adventure that sold out last year! This enchanting experience departs from the Anderson Woburn Transportation Center, offering a delightful escape filled with holiday music, entertainment, and a live retelling of 'The Night Before Christmas.' Don your favorite...

First Night Boston is a cherished New Year's Eve tradition offering a spectacular celebration of arts and community. Attendees can enjoy live music, dazzling fireworks, intricate ice sculptures, and a vibrant parade. This free, family-friendly event transforms the city into a festive hub with diverse performances across multiple venues, welcoming...

The Mayor's Enchanted Trolley Tour brings holiday cheer to Boston neighborhoods for the 28th year. This festive event features Santa visits and tree lightings, spreading holiday spirit to children across the city. The tour travels through various Boston locations over a weekend.