Your Charm City Holiday Bucket List

Browse our loaded list—and check it twice—when planning festive activities this holiday season.

It’s the most wonderful time of the year again. Wintertime holidays loom just ahead, and with that comes great fun set to last through December. With so many can’t-miss events (and so little time) suddenly, festive becomes a fiasco. So here’s a small gift for you this year: a roundup of Baltimore basics to help you get started. As locals can vouch, Charm City delivers on holiday happenings year after year. Below, see our favorites to help you ease into the holiday season the Baltimore way.

12/1: Kick Off the Holiday Season with Mount Vernon’s Monument Lighting

Bring on the fireworks! Thursday, this neighborhood spectacle celebrates 51 years. Leading up to the big show, with breathtaking light displays set to bring magic to Mount Vernon Place, check out food and drink vendors and listen to heartwarming musical acts brought by local performers. This year’s lineup features the Baltimore School for the Arts Twigs program and expert trumpeter Brandon Woody. Washington Monument and Mount Vernon Place. 699 N. Charles St. 5-8 p.m. Free.

12/3: Watch Lighted Boats Set Sail Across The Harbor 

Taking off again this year from Anchorage Marina, this adored downtown tradition is both nautical and nice. Keep cozy from the waterfront and watch in awe as glowing sailboats float their way from Fells Point out to Canton. Canton, Fells Point, Harbor East and Inner Harbor. 3720 Dillon St. 6-8 p.m. Free.

12/3-16: Traverse a Tasty Wonderland at Center Plaza

Thirty-foot ice cream cones, towering lollipop sticks, and a candy cane forest…oh my! In its second year, this sugar-dripping display plans to offer 12 evenings of downtown excitement. Surrounded by sweets, play drag bingo, snap photos with Santa, and fashion a gingerbread rowhome. The Center Plaza attraction will also play host to Christmas karaoke nights, a Frozen family sing-a-long, and 21-plus partying. Center Plaza. Times vary. Free.

12/4: Say Hello to Santa at the Mayor’s Christmas Parade

If all goes to plan, this adored Hampden street party hopes to draw in close to 2,000 guests. Watch as Santa Claus takes to the pavement, surrounded by fierce marching bands, motorcycles and floats. And, as always, stay tuned for the winners of this year’s Miss Yuletide and Miss Yuletide Jr. competition. Hampden and Medfield. 1-4 p.m. Free.

12/10: Shop Around for Goodies at This Year’s Holiday Heap

Make that list and check it twice. This locally loved festival is headed back to Charles Village with gifts for all your favorite peeps. Stock up on handmade trinkets, art to fill those bare walls, and artisanal cuisine brought by the region’s finest makers. Charm City Craft Mafia. 2640 St. Paul St. 10 a.m.-5 p.m. Free.

To 12/24: Grab Your Fill of European Goodies at the German Christmas Village

Inspired by authentic Christmas markets found in Germany (see Nuremberg’s Christkindl) this annual event brings Europe to the Inner Harbor. Scour West Shore Park for toys, eclectic handmade wares, and delicious German bites (think: gooey, melted Alpine Cheese atop a warm baguette, soft pretzels, and potato cakes with schnitzel). Plus, catch carnival attractions and be sure to pose for pictures at the famous Glühwein pyramid. West Shore Park/Inner Harbor. 11am – 7pm. Free.

To 12/30: Raise a Glass and Snap Selfies at the Miracle Pop-Up Bar

Best part about this pop-up cocktail party? Sweet holiday sips come with vintage glasses to match. At Leinie’s Lodge and Beer Garden inside Power Plant Live—which has been decked out with candle-lit table tops, tinsel, and presents dangling from the ceiling—keep things toasty with festive drinks like spicy mulled wine or hot buttered rum. While you’re at it, snap a pic in front of a bow-covered selfie wall, order some holiday-themed appetizers, and say hi to Santa behind the DJ booth. Power Plant Live! 34 Market Place. Times vary. $20.

To 12/31: Climb Aboard a Jolly Trolley at this Festival of Trains

Bundle up the little ones and book it to the B&O Railroad Museum, which turns into a twinkling wonderland this time of year. Take Polar Express train rides, visit Santa’s Winter Village, ogle festive model train layouts, and pose for family pictures with the man in red. (We hear that Mrs. Claus will be there also). Keep an eye out for additional programming like a crafty class for toddlers and a toy drive. B&O Railroad Museum. 901 West Pratt St. 10 a.m.-4 p.m.  $Free-25.

12/31: Per Tradition, Welcome 2023 With Fun and Fireworks in the Inner Harbor

On the heels of last year’s cancellation, flashy, water-facing firework displays will grace the Inner Harbor this year. Stay tuned for coming details on festivities, and get ready to celebrate the kickoff of a great new year for Baltimore. Baltimore Office of Promotion & the Arts. Details TBD. 

To 1/1/2023: Spot Mesmerizing Stoop Displays on Hampden’s 34th Street

Each year, ornately decked out rowhomes turn Hampden’s West 34th Street into a storybook. While strolling down the block, admiring a tree composed of hubcaps, and a stoop adorned with Sesame Street characters, sip decadent hot chocolate from the Charmery while stopping to take photos with loved ones. 726 West 34th Street. 6-10 p.m. Free.

To 1/16/23: Make Life a Winter Rom Com at the Inner Harbor Ice Rink

With mesmerizing harbor views, this ice skating experience is perfect for a play date or a holiday-themed date night. Make a figure eight with friends, or glide hand-in-hand while taking in the frosty magic. Plus, each Thursday at 5:30 p.m., listen for a groovy DJ setlist. Inner Harbor Ice Rink. 201 East Pratt Street. Times vary. $4-175.

1/21/23: Admire This Year’s Entries at the Harbor Point Ice Festival

As in years past, this beloved event will bring the world’s best ice sculptures to Baltimore. Watch as experts take down giant hunks of ice with chainsaws while snagging delicious, local food truck bites and spiked drinks. Central Plaza. 1310 Point Street. Price and timing TBD.