Milton Christmas Events & Things to Do 2025

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...

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...

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 grandeur of Handel's Messiah at the annual Community Messiah Sing hosted by UU Wellesley Hills. This beloved event welcomes everyone from the congregation and surrounding community to join in song or simply enjoy the performance. Featuring professional soloists and a chamber orchestra, with music director Suzie Cartreine conducting...

Experience the timeless holiday classic, The Nutcracker, brought to life by the Commonwealth Ballet. This enchanting performance features stunning choreography, elaborate costumes, and captivating sets, telling the magical story of Clara's adventure. A special sensory-friendly performance is also available, offering a more relaxed and inclusive experience for all audiences.

Immerse yourself in the soulful sounds of New Orleans with the legendary Preservation Hall Jazz Band as they present their 'Creole Christmas' concert. This special performance features a delightful mix of beloved New Orleans jazz classics and festive holiday tunes, all infused with the band's signature vibrant style. It's a...

Get into the holiday spirit with Canadian Brass: Making Spirits Bright. This acclaimed brass ensemble delivers a joyous and festive musical celebration, perfect for the season. Experience their signature blend of virtuosity and warmth as they perform beloved holiday tunes.

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...

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 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...

Experience the timeless holiday magic of The Nutcracker Ballet, presented by Heritage Ballet. Follow young Clara on a whimsical journey as her Nutcracker doll transforms into a prince and leads her through a dreamscape of dancing snowflakes and the Land of the Sweets, culminating in a meeting with the Sugar...

Step back in time with 'It's A Wonderful Life: A Live Radio Play,' a charming theatrical event that recreates the magic of a 1940s broadcast. This production brings the heartwarming story of George Bailey to life with a cast that embodies numerous characters, offering a unique and engaging way to...

Immerse yourself in the magic of the holiday season with Merrimack Repertory Theatre's production of 'A Christmas Carol.' This beloved classic tells the transformative story of Ebenezer Scrooge, brought to life by talented actors in a captivating stage performance. It's a perfect outing for families and anyone looking to embrace...

Discover the festive spirit at the Lower Mills Milton Village Holiday Stroll. This charming event invites visitors to wander through the beautifully decorated village, soaking in the holiday cheer and seasonal atmosphere. It's a perfect opportunity to enjoy the sights and sounds of the season in a picturesque setting.

Discover a treasure trove of handcrafted goods at the 41st annual Dedham Junior Women's Club Craft Fair. Over 80 juried artisans will showcase their unique creations, including jewelry, clothing, home decor, and children's items. Enjoy a festive shopping experience with food and snacks available, and support a great cause as...

The 20th annual Dedham Square Holiday Stroll and Gift Market invites visitors to kick off the holiday season with a festive evening. Explore over 50 street vendors offering unique gifts and treats, enjoy live music and caroling, and delight in free activities for all ages. The highlight includes Santa, Mrs....

Step into a winter wonderland at The Venetian Weymouth's Holiday Pop-Up, returning for its third year. The entire restaurant is transformed into a dazzling spectacle with thousands of ornaments, lush greenery, and sparkling lights, creating an unforgettable dining experience. Guests can savor delicious Italian cuisine, including a special 3-course holiday...

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...

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...

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 magic of the West Acton Village Holiday Stroll! This festive event invites you to explore local businesses offering special deals, participate in a village-wide hunt for prizes, and enjoy the sounds of carolers. Meet Santa Claus and enter a raffle for a chance to win a special basket....

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, handcrafted art and holiday decorations at The Loading Dock Gallery's annual Winter Lights event. This festive showcase features over 30 local artists and artisans, offering a perfect opportunity to find extraordinary gifts and seasonal decor. Browse three rooms filled with beautiful artwork and embrace the spirit of local...

Join the Town of Weymouth for their annual Christmas Tree Lighting & Holiday Festival. This beloved event brings the community together to celebrate the start of the holiday season with festive cheer, entertainment, and activities for all ages.

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...

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.

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...

Unleash your creativity in a hands-on winter cookie decorating class. Learn festive techniques to transform plain cookies into edible works of art, perfect for the holiday season. This class is a delightful way to get into the festive spirit and create sweet treats.

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...

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...

Step back in time at The Old Manse for a captivating holiday tour. This historical colonial home is beautifully transformed for the season, offering an enchanting journey through New England's festive traditions. Discover the magic of Christmas as it was celebrated during the Hawthornes' time, blending rich history with unforgettable...