TONY LEWIS JR
As the calendar turns to December, the region comes alive with twinkling lights, bustling markets, seasonal concerts, and celebrations that capture the heart of the holidays. This week is filled with beloved traditions, community gatherings, and magical moments waiting to be enjoyed — from small-town parades and cozy open houses to festive festivals, sweet treats, and spirited performances. Whether you’re shopping local, savoring seasonal flavors, or soaking in the glow of holiday cheer, there’s no better time to explore, connect, and make memories. Dive in and discover everything happening across our communities this week — the season’s magic starts here.
Midnight Madness
December 4th; Downtown Annapolis, 8:00pm – Midnight
Midnight Madness transforms Downtown Annapolis into a sparkling winter wonderland filled with festive lights, decorated storefronts, live entertainment, and irresistible holiday cheer. Visitors can wander beautifully adorned streets, pop into charming shops offering specials and treats, and soak up the cozy, small-town magic that makes Annapolis one of the top Christmas destinations in the country. It’s the perfect night to gather friends and family, support local businesses, and experience the warmth and wonder of the holiday season in the heart of downtown.
Holiday Art Show 2025 Muddy Creek Artist Guild
December 4th; Hitching post, Lothian 12:00pm – 7:00pm
Kick off the holiday season with the Muddy Creek Artists Guild as they launch their popular Holiday Art Show and Sale, featuring an exciting new location and extended weekends for even more time to explore. Discover unique, handcrafted works from more than 40 talented South County artists—everything from jewelry and photography to ceramics, fiber art, painting, sculpture, and one-of-a-kind gifts. The show offers a festive, creative atmosphere where visitors can meet the artists, find inspiration in fresh new pieces, and shop for meaningful, locally made treasures. With special events planned throughout the run and free admission for all ages, it’s a vibrant celebration of community, creativity, and holiday spirit.
The Festival of Trees continues in loving memory of Mr. Bill Towers.
December 5th; Towers Family Historic Museum, Denton 12:00PM – 5:00PM
Each December, the Towers Family Historical Museum glows with Christmas trees, community spirit, and the legacy of generosity that inspired the Festival of Trees. Hosted in honor of the late Mr. Bill Towers, this cherished tradition continues to uplift Compass Hospice while celebrating the kindness and quiet strength he embodied. The Towers family has opened their museum to the community since 2017, helping raise vital support for compassionate hospice care—a cause deeply meaningful to them, especially after experiencing its impact firsthand during Mr. Bill’s final days at home. Those who knew him remember a humble man who gave freely, helped everyone he could, and asked for nothing in return—except that the Festival succeed for the sake of the families it serves. Today, the event carries forward his legacy of care, gratitude, and community, shining brighter each year in his memory.
Annual Dickens of a Christmas
December 5th; Downtown Chestertown, 5:00pm – 9:00pm
Settle in for a festive evening packed with small-town charm and big holiday spirit. Enjoy cozy carriage rides through the lights, savor freshly shucked oysters and bites from local food vendors, and warm up with beer, wine, and crackling bonfires. The celebration kicks off with an opening ceremony and performances by the KCHS Band, Garnet Elementary Chorus, and the Chester River Chorale, all leading up to an electrifying jam session from The Devils Brigade (formerly the American Rogues). It’s the perfect blend of music, flavor, and community to welcome the season in style.
Annual Tree Lighting Celebration
December 5th; Greater Severna Park and Arnold Chamber of Commerce, Severna Park 5:00pm – 6:30pm
Kick off the holiday season with an evening of pure festive magic at the Annual Tree Lighting Celebration, where twinkling lights, joyful laughter, and community spirit fill the air. Santa arrives in true North Pole fashion to greet families and hear holiday wishes—though the Grinch may try to stir up a little mischief along the way. Enjoy a lively lineup of entertainment with performances from Creative Force Dance Center, the Severna Park Elementary School Chorus, The Edge Dance Complex, Severna Park High School Jazz Band and Cheerleaders, and the Bach to Rock Glee Club. With music, dancing, and holiday fun at every turn, it’s a sparkling start to the season and a wonderful way to celebrate together.
A Vintage Deale’s Open House
December 5th; A Vintage Deale, Deale 5:00pm – 9:00pm
Get into the holiday spirit at A Vintage Deale’s annual Open House, where the shop comes alive with twinkling seasonal décor, whimsical little creatures, and plenty of cozy charm. Guests can browse unique finds in a warmly lit, festive atmosphere while enjoying refreshments and sweet treats. It’s a cheerful, laid-back chance to reconnect with this beloved local spot, soak up some holiday magic, and maybe discover a few special treasures to take home.
Gingerbread Festival
December 5th; Marley Station Mall, Glen Burnie 5:00pm – 8:00pm
Celebrate the sweetness of the season at the Annual Glen Burnie Gingerbread Festival, where creativity, community, and holiday fun come together inside Marley Station Mall. Bakers of all ages and skill levels are invited to craft their most imaginative gingerbread houses—whether entering solo or as a team—and have their creations displayed for two festive weekends. With prizes up for grabs and plenty of whimsical designs to admire, it’s a joyful showcase that spreads cheer and inspires delightful holiday spirit.
A Charlie Brown Christmas with Eric Byrd Trio
December 5th; Maryland Hall, Annapolis 6:00pm – 9:00pm
Celebrate the season with a timeless holiday classic as the acclaimed Eric Byrd Trio brings Vince Guaraldi’s beloved A Charlie Brown Christmas soundtrack to life. Their soulful, swinging renditions of favorites like “Linus and Lucy” and “Christmas Time Is Here” create an atmosphere filled with warmth, nostalgia, and pure holiday cheer. With multiple performance times to choose from — Friday, December 5th at 6pm and 8pm, and Saturday, December 6th at 6pm and 8pm — it’s the perfect way to kick off your festive celebrations with music that delights audiences of all ages.
Centreville Christmas Parade
December 5th; Town Of Centreville, 6:30pm
The Centreville Christmas Parade returns with all the charm and sparkle of the season, filling downtown Centreville with twinkling lights, festive floats, and plenty of small-town cheer. This year’s theme, Bright Nights and Holiday Lights, sets the stage for a magical evening as marching units, community groups, and holiday characters make their way through the streets in a joyful celebration of the season. Bundle up, bring the family, and enjoy one of Centreville’s most beloved holiday traditions.
SMCM Orchestra Concert
December 5th; Nancy R. & Norton T. Dodge Performing Arts Center, Lexington Park 7:00pm – 8:30pm
Enjoy an evening of festive music as the SMCM Symphony Orchestra, under the direction of Jeffrey Silberschlag, presents its annual holiday concert. This spirited performance brings together joyful seasonal selections and the rich, full sound of a talented student orchestra, creating a warm and memorable start to the December celebrations. It’s a wonderful night of artistry, community, and holiday cheer.
Elves for Elders
December 6th; The Rumor Meal, Annapolis 12:00pm
Join Partners In Care for a heartwarming day of giving as the community comes together for the Elves for Elders social event — a festive gathering where volunteers decorate, fill, and deliver cheerful holiday stockings to brighten the season for local older adults. Whether you’re a longtime PIC volunteer or a brand-new elf, this joyful day celebrates connection, compassion, and the magic of small acts of kindness. Guests are encouraged to bring a stocking to fill with thoughtful, comfort-focused goodies, help spread the word to new volunteers, and enjoy the camaraderie of a community dedicated to combating isolation and sharing holiday warmth. It’s a fun, meaningful way to make the season a little brighter for someone who needs it.
Cookies & Cocoa with Claus!
December 6th; Children’s Theatre of Annapolis, 11:00am – 12:30PM
Celebrate the wonder of the season at a cozy holiday gathering filled with cookies, hot cocoa, story time, and a magical visit from Santa himself. Little ones can soak in the excitement as Santa brings cheer, surprises, and plenty of smiles — and parents won’t want to miss the perfect photo moment. Seating is limited and tickets must be purchased online in advance, with all children accompanied by an adult. It’s a sweet, spirited way to experience Christmas through the eyes of a child.
A Colonial Yuletide
December 6th; William Paca House and Garden, Annapolis
Step into the warmth and charm of an 18th-century holiday as Historic Annapolis invites you to celebrate a Colonial Christmas at the William Paca House and the Hogshead Trades Museum. This festive afternoon transports you back to 1775, where music, storytelling, and old-world traditions bring the spirit of early American yuletide to life. With admission granting access to both historic sites, guests can explore at their own pace and experience the season as colonial Annapolitans once did—filled with community, cheer, and timeless holiday magic.
Nutcracker Tea 2025
December 7th; DoubleTree Hotel, Annapolis 10:00am – 5:00pm
Celebrate a beloved holiday tradition at the DoubleTree Hotel in Annapolis with a magical Nutcracker Tea featuring three festive seatings at 10:00 AM, 1:30 PM, and 5:00 PM. Families will enjoy a delicious holiday buffet, an enchanting Nutcracker performance by The Edge Dance Complex, and a heartwarming visit from Santa and Mrs. Claus complete with photos and a classic Christmas story. With a special gift for every child, this cherished seasonal experience is designed to delight guests of every age.
Annapolis Chocolate Binge Festival
December 7th; Calvert and West Street, Annapolis
The Annapolis Chocolate Binge Festival returns to downtown for a sweet and spirited start to the holiday season, transforming the first block of West Street into a lively celebration of treats, lights, and festive cheer. This beloved first-Sunday tradition invites families and chocolate lovers alike to indulge in irresistible sweets, enjoy fun entertainment, browse holiday vendors, and soak in the glow of the dazzling West Street Light Canopy — a joyful kickoff to December that blends community, coziness, and plenty of cocoa-filled magic.
Brigade Holiday Market
December 9th; U.S. Naval Academy-DahlgrenHall, 10:00am – 4:00pm
Get ready to shop, sip, and celebrate at the 10th Annual Brigade Holiday Market, where festive cheer meets local creativity. Dahlgren Hall transforms into a lively holiday marketplace filled with unique gifts from local makers and businesses — perfect for finding something special for everyone on your list. Enjoy complimentary cookies and hot chocolate as you browse, soak up the spirited atmosphere, and take a break from the holiday rush. Open to the public with free admission, this cheerful market welcomes Midshipmen, families, and visitors for a fun, feel-good day of seasonal shopping.
Lights on the Bay
December 3rd – January 1st; Sandy Point State, Annapolis 5:00pm – 9:00pm
Take a magical drive through the holiday season as Sandy Point State Park lights up the shoreline with nearly 70 sparkling animated and stationary displays. This two-mile scenic route along the Chesapeake Bay becomes a twinkling wonderland, perfect for families, friends, and anyone ready to embrace the spirit of the season. Kids will love the nightly scavenger hunt — searching for hidden surprises, answering fun display-themed questions, and entering for a chance to win prizes. With glowing scenes, festive charm, and fun for all ages, this beloved tradition offers a bright and joyful way to celebrate the holidays.
