The holiday season is officially in full swing, and this week’s lineup brings all the sparkle, cheer, and community spirit you could ask for. From festive 5Ks and dazzling light displays to magical markets, beloved annual traditions, and family-friendly performances, there’s something to brighten every kind of celebration. Whether you’re kicking off Thanksgiving with a meaningful run, strolling through glittering displays, hunting for handmade gifts, or soaking in the joy of music, art, and holiday magic, these events are ready to help you savor the season. Dive in, bundle up, and enjoy the warmth, wonder, and togetherness that make this time of year unforgettable.
The Y Turkey Trot Charity 5K
November 27th; The Y in Arnold, Annapolis 8am
Kick off Thanksgiving morning with a festive run that gives back. The Y Turkey Trot Charity 5K brings families, friends, and neighbors together for a feel-good start to the holiday, offering a relaxed, welcoming atmosphere for both runners and walkers. Participants receive a race shirt and bib, and complimentary parking makes arrival easy. Proceeds help provide food and financial support for local families, turning this beloved tradition into a meaningful way to begin the day of thanks.
Lights on the Bay
November 27th – January 1st; Sandy Point State Park, Annapolis 5:30pm
Enjoy a sparkling two-mile journey through Sandy Point State Park as more than 70 animated and stationary light displays illuminate the roadway in a dazzling holiday showcase. Kids can join in the fun with a nightly scavenger hunt, searching for hidden items, answering display-themed clues, and earning a chance to win prizes. And for an extra touch of magic, Santa himself makes a special appearance on Thanksgiving Day. It’s a festive tradition with something to delight every member of the family.
40th Festival of Trees
November 29th- December 2nd: Tidewater Inn, Easton
The Festival of Trees returns for its 40th year with “Forty Years of Silver and Gold,” celebrating a beloved Eastern Shore tradition that has raised nearly $4 million in support of Talbot Hospice. What began in 1985 as a heartfelt tribute by founders Midge Fuller and Leslie Ware has grown into a multi-day community celebration filled with shimmering trees, festive displays, family fun, and the spirit of giving. Guests can explore more than 100 exquisitely decorated trees in the Tidewater Inn’s Gold Ballroom, enjoy live performances, shop for seasonal gifts, and take part in special traditions like the Santa 5K Fun Run/Walk, Santa’s Workshop, Carols by Candlelight, and the stunning 12-foot poinsettia tree. With keepsake luminaries, beautifully crafted wreaths, and joyful moments woven through the entire weekend, the Festival of Trees continues to honor loved ones, uplift the community, and shine in support of Talbot Hospice.
Kennedy Krieger’s Festival of Trees
November 28th; Maryland State Fairgrounds, Timonium 10:00am – 7:00pm
Step into a holiday wonderland as the festival fills the weekend with more than 800 decorated trees, wreaths, and gingerbread houses, each crafted by local businesses, community groups, schools, and imaginative individuals. Wander aisles of twinkling lights, themed displays inspired by the year’s biggest trends, and handcrafted details that make every tree feel like its own work of art. Santa will be visiting throughout the event for festive photos and wish-list chats, while amusement rides, games, crafts, and live entertainment keep families smiling from morning to night. With something magical around every corner, it’s a joyful holiday tradition for all ages.
Christmas Village in Baltimore
November 26 – December 24th; Inner Harbor- West Shore Park, Baltimore
Christmas Village in Baltimore brings European holiday magic to the Inner Harbor, capturing the charm of a traditional German Christmas market with more than 60 vendors nestled in cozy wooden booths. Inspired by Nuremberg’s famed Christkindlesmarkt, this beloved event fills the season with twinkling lights, festive food, and Old World cheer. Guests can shop handcrafted gifts, sip warm Glühwein beneath the glowing mulled-wine pyramid, enjoy bratwursts fresh off the grill, and explore both indoor and outdoor attractions — including the Carousel, Ferris Wheel, beer garden, and heated tent. It’s a joyful, bustling celebration that has made Christmas Village one of the top holiday markets in the country and a must-visit tradition for families and friends.
Circus Pop the Holiday Bubble-bration
November 30th; Children’s Theatre of Annapolis, 2:00pm – 3:00pm
Get ready for pure wonder at Circus Pop! The Giant Bubble Show, a one-of-a-kind performance that blends high-energy circus skills with breathtaking bubble artistry. Veteran performer Logan Jimenez dazzles audiences with fire eating, daring escapes, and bubble creations so spectacular they feel almost unreal. From towering 15-foot soap bubbles to swirling bubble sculptures and even a bubbling volcano, every moment is crafted to captivate. It’s a joyful, imagination-filled show designed to amaze guests from the littlest viewers to the young at heart, making it a magical outing for the whole family.
Annapolis Tree Lighting
November 30th; Market House and City Dock, Annapolis 3:00pm
Downtown Annapolis comes alive on November 30 as the annual Grand Illumination brings families, friends, and visitors together to welcome the start of the holiday season. From 3:10 to 3:40 p.m., the Annapolis Symphony Academy Aquarius Wind Ensemble fills the waterfront with festive orchestral music, setting the tone for an evening of sparkling lights and seasonal cheer. As the city’s Christmas tree is illuminated, the historic streets glow with warmth, carols drift through the crisp air, and the community gathers to celebrate this beloved tradition that transforms Annapolis into a winter wonderland.
Mistletoe & Martinis: Providence of Maryland’s Holiday Sip & Shop
December 2nd; Providence Greenhouse, Annapolis 6:00pm – 9:00pm
Get into the holiday spirit at Providence’s Mistletoe & Martinis event, a cozy evening of shopping, sipping, and seasonal cheer. Guests can browse unique gifts and décor, handcrafted pottery from the Providence Pottery & Arts Studio, and fresh holiday greens from Providence Greenhouses, including cedar garlands, noble fir wreaths, mistletoe, and poinsettias. Complimentary seasonal martinis and festive bites await by the fire pit, all beneath a canopy of twinkling lights. Whether you’re visiting with friends, family, or stopping by on your own, it’s the perfect way to welcome the season and find something special for everyone on your list.
