Annapolis Christmas Events & Things to Do 2025

Step into a festive Downtown Annapolis Winter Wonderland during Midnight Madness. This cherished holiday tradition invites you to stroll through streets adorned with twinkling lights, festive decorations, and a towering Christmas tree. Enjoy extended shopping hours until midnight, discover unique gifts from local boutiques, and soak in the magical atmosphere...

Discover the Annapolis First Sunday Arts Holiday Market, a festive gathering on historic West Street. Browse over 100 artisan vendors showcasing handmade pottery, jewelry, paintings, and more. Enjoy live music from local artists and savor delicious treats from food vendors. It's the perfect destination for unique holiday shopping and a...

Discover the charm of the Annapolis Holiday Market, a beloved tradition set against the historic backdrop of Annapolis, Maryland. This festive event showcases over 100 local and regional artisans, offering a wide array of crafts, handmade gifts, and specialty food items. Visitors can savor seasonal treats like hot chocolate and...

Get into the holiday spirit at the Advent Market Celebration! This festive event offers a delightful start to the season with a wide array of handmade crafts and artisan vendors. Enjoy live music, caroling, and delicious food truck options. Families will love the kids' crafts, petting zoo, and pony rides,...

Discover a festive holiday market at Severn Run High School, featuring a curated selection of artisanal crafts and unique gifts. This community event is the perfect place to find special holiday treasures and support local vendors. Enjoy a cheerful atmosphere with festive treats and beverages available.

Discover unique, handcrafted gifts and festive holiday items at the Severn Run High School Cheerleading Holiday Craft Show. This event brings together local artisans and vendors, offering a wonderful opportunity to find special presents while supporting the school's cheerleading squad. Immerse yourself in a cheerful atmosphere and get a head...

Savage Mill Yuletide transforms the historic mill into a festive wonderland. Discover unique gifts at the Holiday Makers Market, meet Santa and Mrs. Claus, and enjoy live music. Don't miss the magical bridge and tree lighting ceremonies, plus a special exhibition on the mill's Christmas past.

Experience the heartwarming tradition of Christmas in St. Michaels, celebrating 39 years of community service. This beloved event offers a chance to create lasting holiday memories while supporting local non-profit organizations. Purchase the exclusive 2025 Limited Edition Collectors Ornament, with all proceeds directly benefiting the Bay Hundred community. Join in...

Get ready for Midnight Madness, a special late-night shopping event in St. Michaels. Local businesses open their doors for extended hours, offering a festive atmosphere for holiday shoppers. It's the perfect opportunity to find unique gifts and enjoy the start of the holiday season in a charming setting.

Step into a magical European Christmas wonderland at Baltimore's Inner Harbor. This authentic German Christmas Market features over 60 international vendors offering unique gifts, crafts, and delicious festive foods. Enjoy mulled wine, German beer, and special events like wine tastings and meet-and-greets with Santa. It's a perfect destination for holiday...

Discover Baltimore's ultimate holiday shopping destination at the Holiday Makers Market. This vibrant event transforms the Inner Harbor into a festive hub, showcasing dozens of local artists and makers. Find unique gifts, handcrafted decorations, and enjoy a community art project creating upcycled umbrella jellies for sustainable decor. It's the perfect...

Experience the festive spirit at the Silver Spring Christmas Market and Holiday Craft Show. This event brings together a curated selection of local artisans and vendors, offering a wide variety of handmade crafts, unique gifts, and seasonal treats. Discover everything from intricate jewelry and artwork to delicious baked goods and...

Discover a treasure trove of unique gifts and delightful treats at the DC Holiday Market in Dupont Circle. This festive market showcases over 35 local artists, crafters, and small businesses offering worldwide handicrafts and boutique brands. Find the perfect holiday presents amidst bright, festive decor in a vibrant neighborhood setting.

Ballet Theatre of Maryland presents a captivating, Annapolitan-inspired Nutcracker. This unique production reimagines the beloved classic with local historical elements, vibrant costumes, and original choreography. Follow Clara's dream journey through 19th-century Annapolis, from snow-dusted gardens to a Land of the Sweets filled with local confections. It's a festive holiday treat...

Step into a winter wonderland with Irving Berlin's 'White Christmas,' a dazzling musical adaptation. This heartwarming production brings the classic songs and beloved story to life on stage, offering a perfect festive escape for the holiday season. Prepare for a magical theatrical experience filled with joy and holiday cheer.

Step into a magical winter wonderland with "The Nutcracker 2025." This enchanting ballet performance is a timeless classic, perfect for the whole family. Experience the magic of sugar plum fairies and toy soldiers as the story unfolds, sparking imagination and touching hearts. Keep the tradition alive with this spectacular holiday...

Step back into Victorian London for an acclaimed adaptation of Charles Dickens' A Christmas Carol at the Bowie Center for the Performing Arts. This beloved story unfolds with music, magic, and heart, following Ebenezer Scrooge's journey of rediscovery. It's a cherished holiday tradition perfect for families.

The National Ballet Company returns to the Prince George's Publick Playhouse with their enchanting rendition of 'The Nutcracker.' This timeless holiday classic promises a magical experience for all ages, featuring stunning choreography, vibrant costumes, and Tchaikovsky's iconic score. Follow Clara's journey through a whimsical winter wonderland as the story of...

Get ready to groove to the soulful sounds of Motown and classic holiday hits! The BRENCORE ALL STARS are set to deliver an unforgettable performance featuring legendary artists. This popular show sells out quickly, so secure your tickets early for a festive concert experience.

Get into the holiday spirit with the Columbia Orchestra's 'Holiday Pops' concert. This festive event features beloved seasonal music performed live, perfect for families looking to celebrate the season. Experience the joy and magic of holiday tunes brought to life by talented musicians.

Experience the timeless tale of Ebenezer Scrooge's redemption in this enchanting production of 'A Christmas Carol.' This music-infused adaptation brings Dickens's Yuletide classic to life with beloved characters and a vibrant children's ensemble. Acclaimed actor Craig Wallace returns to embody Scrooge in Ford's cherished annual tradition, promising a 'rich visual...

Immerse yourself in the magic of the holidays with The Washington Ballet's iconic production of The Nutcracker. This cherished DC tradition, running from November 29 to December 28, 2025, features over 380 dancers in a spectacular performance set in historic Georgetown. Experience the familiar story with unique local twists, including...

Ring in the New Year with an unforgettable celebration on the water in Annapolis. This exclusive yacht party offers a DJ, dancing, and a complimentary beverage, all while providing a front-row seat to the city's 9:00 PM fireworks display. Alcoholic and non-alcoholic drinks are available for purchase from the full-service...

Get ready for a decadent celebration of all things chocolate at the Annapolis Chocolate Binge Festival! This family-friendly event transforms the first block of West Street into a chocolate lover's paradise. Alongside a delightful array of chocolate vendors, the festival hosts an exciting Gingerbread House decorating contest, inviting everyone from...

Get ready for the most wonderful crawl of the year! The Official 12 Bars of Christmas Crawl® descends upon Baltimore on Saturday, December 20th, 2025. Don your most festive holiday attire, from Santa suits to ugly sweaters, and prepare for a day of spirited fun. Attendees receive a commemorative Santa...

Join Santa for a delightful breakfast buffet at the historic B&O Railroad Museum. This family-friendly event includes a special gift for every child, photo opportunities with Santa, and a charming train ride. It's the perfect way to kick off the holiday season with a memorable experience for all ages.

Celebrate the New Year with a touch of sophistication at the B&O Railroad Museum's New Year's Tea. This elegant English afternoon tea, hosted in the historic 1884 Baldwin Roundhouse, offers a delightful blend of festive cheer and refined indulgence. Guests will enjoy a scenic journey aboard the Mile One Express...

Experience a quintessential Washington, DC holiday tradition at The Nutcracker Tea Party. This festive event offers delightful treats and family fun, culminating in a choice of attending either the afternoon or evening performance of the beloved Nutcracker ballet at the Warner Theatre. It's a perfect way to immerse yourself in...

Experience a unique holiday spectacle as decorated boats illuminate the waterways in a dazzling parade. This event offers a festive maritime twist on traditional light displays, showcasing creative and vibrant holiday decorations on vessels.

Embark on a magical journey through the Symphony of Lights, a breathtaking drive-through holiday spectacle. This immersive experience transforms the night into a wonderland of animated and synchronized light displays, all set to the enchanting sounds of holiday music. It's the perfect way to soak in the festive spirit from...

Experience the magic of the holiday season at the National Christmas Tree Lighting Ceremony. This cherished national tradition features the beautifully decorated National Christmas Tree, illuminated with thousands of lights. Visitors can also admire unique ornaments representing every U.S. state and territory, creating a festive and inspiring atmosphere.

Journey back to 1775 for a Colonial Yuletide celebration in historic Annapolis. Experience the holidays as they were in early America with music, storytelling, and traditional festivities at both the William Paca House & Garden and the Hogshead Trades Museum. Meet Santa, enjoy colonial crafts, and discover how Annapolitans prepared...

Embark on Annapolis' beloved holiday tradition, the Jolly Express Cruise. This delightful 45-minute voyage on Spa Creek offers a magical 'sleigh ride' experience complete with holiday music and warm hot cocoa. Captain Santa or Mrs. Claus will guide the festively adorned Miss Anne, creating cherished memories for all aboard. It's...

Get ready for a magical evening at 'A Budweiser Clydesdale Miracle on West Street,' a festive prelude to the Military Bowl. This event features the renowned Budweiser Clydesdales, alongside a vibrant street scene with food trucks, vendors, and engaging activities for all ages. It's the perfect way to kick off...

Get ready for a season of festive cheer in Bowie! While specific plans for this year are announced in the fall, past events have included magical visits from Santa, charming trainspotting days, and delightful holiday movie screenings. Explore the historic Belair Mansion during its open house and admire the community's...

Experience the magic of the holiday season at the annual Laurel Armory Illumination. This cherished tradition officially kicks off the festive period with a special ceremony. Prior to the illumination, enjoy a vibrant Holiday Parade that winds its way through the city, starting from City Hall.

The acclaimed Morgan State University Choir is set to perform at the annual Monument Lighting ceremony. This special holiday event will feature the choir's world-class vocal talents against the backdrop of the historic Washington Monument in Baltimore. It's a unique opportunity to enjoy a festive musical performance during the holiday...

Step into a festive wonderland at the Holiday Train Garden, hosted at the historic Baltimore and Ohio Ellicott City Station Museum. This enchanting display features meticulously crafted model trains winding through charming holiday scenes. It's a perfect, family-friendly outing to experience the magic of the season in a unique historical...

Immerse yourself in 'The Gift of Art 2025,' an exhibition at The Artists' Gallery of Ellicott City. This event features a stunning array of original artwork from talented local artists, spanning mediums from ceramics and wood turning to paintings and photography. Discover unique pieces perfect for gifting or adding to...

The U.S. Capitol Christmas Tree Lighting Ceremony is a cherished national tradition. Each year, a magnificent tree, sourced from a different national forest across the United States, is selected and transported to the West Front Lawn of the U.S. Capitol. Visitors can witness the tree's grand arrival with a police...

Experience the joy of the Montgomery County Thanksgiving Parade, a cherished annual tradition! This vibrant celebration features dazzling floats, lively marching bands, and whimsical 12-foot inflatable turkeys. The parade culminates with a special appearance by Santa Claus, making it a perfect festive outing for the entire family to kick off...