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. Below, see some of our favorites to help you ease into the holiday season the Baltimore way.

12/7: Kick Off the Holiday Season with Mount Vernon’s Monument Lighting

Bring on the fireworks! This neighborhood spectacle celebrates 52 years this year. Before the 8 p.m. lighting of the Washington Monument at Mount Vernon Place, you can check out onsite food and drink vendors and listen to heartwarming local musical acts like the Baltimore School for the Arts’ TWIGS program and the Peabody Brass Ensemble. Don’t forget to stop by neighborhood bars and restaurants while you’re in the area. Mount Vernon Marketplace, The Ivy Hotel, The Owl Bar, Ulysses, and Wet City (which will once again be serving spiked cider and Chartreuse hot chocolates in to-go cups) are among those hosting parties with food and drink specials. Washington Monument and Mount Vernon Place. 699 N. Charles St. 5-8 p.m. Free.

12/9: Find Unique Gifts at Charm City Craft Mafia’s Holiday Heap

Make that list and check it twice. This annual pop-up market 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 other one-of-a-kind gifts brought by the region’s finest makers. Of course, Holiday Heap is a standout, but there are plenty of other holiday markets happening throughout the month. Check out more, here. Charm City Craft Mafia. 2640 St. Paul St. 10 a.m.-5 p.m. Free.

12/12: Spread Love and Light at the Annual Hanukkah BrewHaha

The ninth-annual event hosted by the local chapter of Repair the World—an organization that connects Jewish young adults to service opportunities in their communities—is taking over the taproom at Union Craft Brewing in celebration of the Festival of Lights. Throw on your coziest Hanukkah attire to light the menorah, scarf down latkes, sip Union brews, enjoy live DJ music, try your hand at a raffle, and grab a scoop from The Charmery for dessert. Get there on time—the first 100 people through the door will receive a take-home pint glass.

12/16: Celebrate Kwanzaa with BLK Ass Flea Market

As part of Baltimore Peninsula’s Holiday Remix lineup of community programming, the South Baltimore development is teaming up with the BLK Ass Flea Market to host a Kwanzaa edition of the annual shopping bazaar highlighting Black-owned businesses. While browsing handmade items and stocking stuffers from more than 30 local vendors, snap photos with Black Santa, groove to live DJ tunes, and sit in on workshops that delve into the seven principles of Kwanzaa.

To 12/24: Grab Your Fill of European Goodies at the Baltimore 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

Leinie’s Lodge and Beer Garden inside Power Plant Live has once again been transformed into a wonderland of tinsel, lights, and vintage decorations galore. Throw on your holiday best and head to the pop-up bar to enjoy festive beverages like the “Christmapolitan” and “Snowball Old Fashioned.” While you’re at it, roast tableside s’mores, enjoy holiday film screenings, and create gingerbread masterpieces. Power Plant Live! 34 Market Place. Times and prices vary. 

To 12/31: Climb Aboard a Jolly Trolley at the B&O’s 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-$27.

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, a stoop adorned with classic characters, and the famous Hanukkah House, be sure to stop and snap a few photos with loved ones. 726 West 34th Street. 6-10 p.m. Free.

To 1/15/23: Make Life a Winter Rom Com at the Local Ice and Roller Rinks

With mesmerizing harbor views, the Inner Harbor ice rink 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. This year, locals can also take advantage of The Roller Wave, a new indoor installation at the Baltimore Peninsula that will be operating throughout January. Additionally—thanks to the work of the Youth Resiliency Institute in partnership with Baltimore City’s Department of Recreation and Parks, South Baltimore’s Middle Branch Park will play host to a pop-up rink this season. Sadly, a community skating event originally scheduled for December 10 has been postponed due to weather, but you can follow updates, here201 East Pratt Street. Times vary. $12-100.

1/27/24: Admire This Year’s Entries at the Harbor Point Ice Festival

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

To 2/2024: Pack Up the Car to See a Dazzling Holiday Light Show 

Of course, no holiday season would be complete without marveling at the twinkling light displays offered throughout the region. Whether you’re looking to drive, walk, bike, or ice skate your way around a local showcases, our comprehensive travel guides have everything you need to plan an outing. Check out this piece for illuminated displays closer to home (including the fan-favorite Merriweather Symphony of Lights and brand new Charm City Lights at Druid Hill Park). Or, if you’re down for a road trip, access this guide for can’t-miss light shows happening throughout the Mid-Atlantic.