The Talent Machine Presents "A Merry Mix-Up" Holiday Spectacular
Your holiday calendar is officially booked. From twinkly late-night shopping and waterfront light parades to cozy concerts, merry markets, and hometown parades packed with surprises, this week is full of reasons to get out and soak up the season. Whether you’re chasing that classic Christmas feeling, hunting for gifts you’ll actually be excited to give, or just looking for something fun to do after work, you’ll find it here. Pick one event or make it a whole festive lineup—either way, there’s plenty of cheer waiting just down the road.
Midnight Madness
December 11th, Downtown Annapolis, 5:00pm
Midnight Madness turns downtown into a twinkling holiday playground, where decorated storefronts, garlands, glowing lights, and free street entertainment make it feel like you’ve stepped into a classic Christmas scene. Wander from shop to shop for cheerful specials and sweet treats, browse galleries and boutiques for gifts you’ll actually be excited to give, and soak up that cozy, small-town magic that makes the season feel extra special. It’s the kind of night made for bundling up with friends or family, shopping local, and letting the holiday spirit do the rest.
U.S. Naval Academy Band Holiday By the Bay Concert
December 11th; US Naval Academy Main chapel, Annapolis 7:30pm - 9:00pm
Holiday by the Bay is a festive, free holiday concert featuring multiple Naval Academy Band ensembles and special guests from the Brigade of Midshipmen. Expect a lively mix of multicultural favorites that moves from classic carols to modern seasonal picks, all performed in the stunning setting of the Main Chapel. It’s the kind of feel-good night that makes you want to hum along, soak up the atmosphere, and officially call the holiday season “on.” Families are welcome, and Santa might even make a surprise visit to delight kids (and kids-at-heart) with a little extra cheer. Best of all, no tickets are required, so it’s an easy, last-minute-friendly plan for a December evening. Come for the music, stay for the tradition, and leave with your holiday spirit fully recharged.
Christmas in St. Michaels 2025
December 12th – 14th; Downtown St. Michaels
Christmas in St. Michaels returns December 12–14, 2025, bringing a whole weekend of small-town holiday charm and feel-good tradition. It’s the kind of event that turns a simple stroll into a memory—full of seasonal cheer, community spirit, and that unmistakable “Christmas is here” feeling. Keep an eye out for updated 2025 details as they roll in, because the schedule is packed with reasons to come back year after year. A favorite highlight is the Limited Edition Collectors Ornament, a must for longtime fans and the perfect keepsake if you’re starting a new tradition. Even better, ornament and product proceeds support local nonprofit organizations, so your holiday shopping does real good. Come ready to celebrate, say hello to Santa, and soak up the joy of giving that makes this weekend so special.
Oxford Holiday Market 2025
December 12th – 14th; Oxford Community Center, Oxford
The Oxford Holiday Market returns for a festive weekend of shopping, snacking, and small-town holiday charm. Browse a curated mix of artisan vendors offering handcrafted gifts and seasonal décor, perfect for crossing a few special names off your list. When you’re ready to refuel, swing by the café for cozy lunch options and sweet treats like apple strudel, stollen, and cookies paired with a warming cup of tea. With free admission and plenty of cheerful browsing, it’s an easy, feel-good way to spend a winter weekend celebrating the season.
The Talent Machine Co. Presents "A Merry Mix-Up" Holiday Spectacular!
December 12th – 23rd; Indian Creek School, Crownsville 7:00pm – 9:15pm
The Talent Machine Company’s annual Holiday Spectacular returns December 12–23 with A Merry Mix-Up, a high-energy musical revue that’s become a can’t-miss family tradition. With both evening and matinee performances available, it’s easy to make this festive show part of your holiday plans. Expect a fast-moving blend of favorite seasonal songs, crowd-pleasing dances, and a playful storyline that asks the big question: what happens when the holidays get a little… mixed up? Performed by an impressive cast of young talent ages 5 to 18, the production delivers big holiday spirit with plenty of heart and sparkle. And yes—there are special appearances from Rudolph, Frosty, the Elves, and Santa himself, making it extra magical for kids (and nostalgic for grown-ups, too). Tickets are $20, and it’s the kind of cheerful, feel-good outing that leaves everyone humming on the way home.
Governor and First Lady Moore to Welcome Marylanders for Holiday Open House
December 13th; Government House, Annapolis 9am – 12:00pm
Step inside Government House for a rare, feel-good holiday tradition as Governor Wes Moore and First Lady Dawn Moore welcome Marylanders for a public Holiday Open House. Stroll through the beautifully decorated rooms, soak up the seasonal atmosphere, and enjoy a festive moment that celebrates the heart, resilience, and togetherness that makes Maryland feel like home. It’s a simple, special way to get into the holiday spirit—perfect for anyone who loves a little history, a little sparkle, and a lot of community cheer.
Holiday Traditions Tour of the William Paca House
December 13th; William Paca House and Garden, Annapolis 4:00pm – 5:00pm
Step into the glow of the season with a festive, candlelit tour of the William Paca House, beautifully dressed for the holidays. Bring family and friends and enjoy a cozy one-hour guided walk through the home of a Signer of the Declaration of Independence, led by a knowledgeable docent who brings the house—and its history—to life. Along the way, you’ll learn how 18th-century Annapolis families celebrated, hosted, and prepared their homes for holiday guests, with special focus on traditions in the Paca household. Expect charming seasonal décor, warm candlelight, and a little extra atmosphere with music and garlands throughout the mansion. The experience ends on a sweet note with a treat to enjoy and a take-home recipe so you can carry a bit of historic holiday cheer back to your own kitchen. It’s a festive way to kick off the season, slow down, and soak in the spirit of an Annapolis holiday long ago.
Eastport Yacht Club Lights Parade
December 13th; Annapolis Harbor/Ego Alley, Annapolis 5:00pm – 9:00pm
Born from a few Eastport Yacht Club members cruising the harbor and singing carols on a chilly December night in the 1980s, this bright Annapolis tradition has been turning heads for 40 years. What started as a spirited, small-scale loop around the water quickly became something bigger once boaters began adding twinkling lights and playful decorations—transforming the harbor into a floating holiday parade. Today, the Lights Parade is a beloved seasonal highlight, with illuminated boats gliding by in a sparkling show that feels equal parts cozy and spectacular. You can catch it from shore for free, or make a night of it with one of the on-the-water viewing cruises offered by local operators. Either way, it’s pure Annapolis magic—carols, community, and a harbor that shines.
Heroes Holiday Market
December 14th; Heroes Pub, Annapolis 8:00am – 11:00am
Start your Sunday on a festive note at the 6th Annual Heroes Holiday Market, packed with cheerful vibes and plenty of local finds. Browse and shop from 35+ local vendors offering gifts, goodies, and holiday favorites that make wrapping up your list a whole lot more fun. Families can say hello to Santa and friends, adding an extra dose of seasonal magic while you stroll. Be sure to check out the massive Heroes Holiday Raffle, all benefiting The Chesapeake K9 Fund—so every ticket supports a great cause. Come for the shopping, stay for the community spirit, and leave with gifts (and maybe a little extra holiday glow).
Mayor’s Christmas Parade
December 14th; Hampden, Baltimore 1:00pm – 4:00pm
Get ready for a holiday parade that’s equal parts hometown charm and can’t-believe-your-eyes fun. Expect colorful floats, local personalities, and lively bands bringing the streets to life with nonstop seasonal energy. Keep an eye out for surprise favorites like Darth Vader and the Boumi Shriners, because this lineup loves to mix classic cheer with a little extra wow. And of course, the grand finale belongs to Santa Claus, wrapping it all up with the kind of magic that makes the whole crowd smile. It’s the perfect family outing—bundle up, grab your spot, and enjoy the show.
Winter Concert: Lyra Chamber Orchestra & Aquarius Wind Ensemble
December 14th; Maryland Hall, Annapolis 5:00pm
Join the Annapolis Symphony Academy for a cozy Winter Concert featuring the Lyra Chamber Orchestra and the Aquarius Wind Ensemble. This free recital shines a spotlight on talented student musicians as they fill the evening with seasonal favorites and concert highlights that feel made for December. It’s a wonderful chance to support young performers, soak up the spirit of the season, and enjoy an uplifting night of live music with the community. General seating is available, so come ready to settle in and let the sounds of the season carry you.
Songs of the Season
December 14th; Eastport United Methodist Church, Annapolis
Celebrate the season with Songs of the Season, featuring holiday favorites performed by the Naptown Philharmonic Orchestra Chorus in its debut concert. Directed by Jeanne Kelly, this festive program brings bright harmonies, classic carols, and joyful seasonal selections together for a warm, community-filled evening of music. It’s an easy, feel-good way to slow down during a busy month and soak up the sounds of the holidays—perfect to enjoy with friends, family, or anyone who loves a good sing-along moment from the audience.
