Get Jolly With Our December Date Night Ideas and Events in Maryland

Grab a cup of cheer and fun with our selection of adult happenings in December, whether you want to spend a romantic night with your significant other or a night out enjoying holiday festivities with friends!

Events ongoing throughout December:

be6a0cde13a86df3a08087ee692e0281Through Jan. 6
Georgetown Glow: Light Art Festival
Experience the sparkle of the season at Georgetown GLOW, a spectacular outdoor public light art installations. 5–10 p.m. Georgetown Waterfront Park, Washington.

Jolly Express Cruise
Fridays, Saturdays and Sundays in Dec. Enjoy a 45-minute Spa Creek cruise aboard the Miss Anne, while the boat is decorated in reindeer antlers and a lit up red nose. Reservations recommended. $13–$23. 6, 7 and 8 p.m. Annapolis City Dock, Annapolis.

A Christmas Carol
Weekends through Dec. 30. Adapted from the novel by Charles Dickens, “A Christmas Carol” is a beloved holiday performance. $30–$40. Annapolis Shakespeare Company, Annapolis.

1 Saturday
Holiday Candlelight Stroll
Fridays and Saturdays (except Dec. 8). Holiday walk through downtown Annapolis. $12–$21. 7–8:30 p.m. Downtown Annapolis.

2 Sunday
Chocolate Binge Festival
Are you a chocoholic in need of a fix? You won't want to miss the 4th Annual Chocolate Binge Festival in Downtown Annapolis. Free. 5 p.m. Annapolis.

Get in the holiday spirit with Pentatonix at the Anthem on December 2 and 3, shows are at 7 p.m. $59.50 - $149.50.

4 Tuesday
Love, Factually
4–31. This holiday satire from the twisted minds at Second City, gets to the truth of December life, love, and romance. Whether you love or hate the movie Love, Actually, you're going to fall in love with this mashup of parody, original comedy, music, improv, and audience participation. $50–$75. Kennedy Center, Washington, D.C.

Chanukah Brew Ha Ha
Throw on your favorite ugly sweater and head to the best beer fest in Baltimore, complete with Chanukah treats, 3D printed mezzuzahs and fun ways to tap into the spirit and themes of Chanukah. $18. 7–10 p.m. Union Craft Brewing, Baltimore.

5 Wednesday
The Caring Tree Girls’ Night Out
This evening of merriment, sparkle, and cheer features culinary treats, sweets, and libations with holiday music favorites on the piano. A minimum donation of $35 is requested for entry. 6–8 p.m. All proceeds go directly to support the Wellness House of Annapolis.

Beer and Wine Tasting
Immerse yourself in Baltimore’s brewing industry—past and present—during this panel discussion with local brewers featuring tastings from each company. . Registration required. $45. 6:30–9 p.m. Baltimore Museum of Industry.

midnight madness6 Thursday
Midnight Madness Annapolis
Dec. 6, 13 and 20. Stroll through downtown Annapolis as shops remain open until midnight, and enjoy carolers, food, drinks, special deals and fun for the kids. Free. 6 p.m.–midnight. Downtown Annapolis.

A Christmas Carol
Dec. 6–16. Be transported to the streets of Victorian London and the counting house and bedchamber of Ebenezer Scrooge. In the revelations of his visitors and in his memory, we are transported to times and places of Scrooge's past, present, and future. Buy early! $10. See websites for showtimes. Colonial Players, Annapolis.

7 Friday
A Celebration of Christmas
The Annapolis Chorale and the Annapolis Chamber Orchestra take the stage for this annual holiday favorite that includes a joyous blend of everyone’s favorite songs, like “White Christmas” and “It’s the Most Wonderful Time of the Year.” Not to be outdone in the holiday cheer department, the Annapolis Chamber Orchestra takes the spotlight for the classic “Sleigh Ride.” $58. Maryland Hall for the Creative Arts, Annapolis.

Midnight Madness Ellicott City
Come out to support Ellicott City businesses on this 40th annual Midnight Madness, which will feature visits with Santa (4–8 p.m. at the firehouse), strolling carolers, late-night shopping, libations, and the tree lighting. Free. 6 p.m.–midnight. Historic Ellicott City.

8 Saturday
Shells and Bells
This party on the Creek will feature a front row seat to the Eastport Yacht Club’s Parade of Lights. As part of the evening guests will enjoy specialty cocktails, wine and spirits tastings, local food, live music, oysters & champagne, and an auction. $125. 6–10 p.m. Historic Charles Carroll House & Gardens, Annapolis.

10 Monday
Annapolis Christmas Show
10–11. Local artists perform a mix of original and classic holiday songs. $42. 7 p.m. Rams Head On Stage, Annapolis.

14 Friday
Holiday Pops with Cathie Ryan
The Annapolis Symphony Orchestra will celebrate the holidays with Celtic flair this season, with Irish-American vocalist Cathie Ryan for the annual Holiday Pops concert, one of the Symphony’s most popular events. $47–$95. 8 p.m. Maryland Hall for the Creative Arts, Annapolis.

speedo run15 Saturday
Santa Speedo Run
Strip down to your Speedos for this annual run through downtown Annapolis! Post-run party with live music and plenty of libations at O'Briens. Bring an unwrapped children's toy or book to donate. Register to run/walk. $25. Check-in and pre-drinks at 10:30 a.m.; run starts at 12:30. City Dock, Annapolis.

20 Thursday
A Christmas Tour at Maryland Hall
An evening of holiday jazz music featuring Billboard charting violinist Chelsey Green and the Green Project and local legendary Jazz Saxophonist Art Sherrod Jr. with singer/songwriter Lolita Chambers. $31. 7:30 p.m. Maryland Hall for the Creative Arts, Annapolis.

21 Friday
Dublin 5
Celtic music to enjoy. Their eclectic mix of traditional roots and blazing instrumentals with an amped up rock twist make for a great show! $27. 8:30 p.m. Rams Head on Stage, Annapolis.

22 Saturday
A Holiday Drag Brunch
This is a true variety show with a Holiday twist, as entertainers determine if you've been naughty or nice over the last year while they perform a chorus of your favorite holiday inspired songs, do comedic skits, and make you say “OMG” as they dance, twirl, and somersault to high-energy dance numbers. $20. 12:30 p.m. Ram’s Head on Stage, Annapolis.

TSO2018 WinterTour 1080x1080 a41221761523 Sunday
Trans-Siberian Orchestra
‘The Ghosts of Christmas Eve’ features the Best of TSO and more! $42–$80. 3 p.m. Capital One Arena, Washington, D.C.

28 Friday
The Roots Holiday Tour
Catch the Roots live on tour as the legendary hip-hop group plays a standing-room only performance to end out 2018. $70. 8 p.m. The Fillmore, Silver Spring.

29 Saturday
Battle of the Birdland Wing Festival
A wing-eating competition, sauce competition and facemelter challenge (waiver required) mark this third annual wing festival. Noon–4 p.m. $25. Delia Foley’s, Baltimore.

31 Monday
Annapolis New Year’s Celebration
Festive activities for the whole family start at 3 p.m. at Weems Whelan park behind Maryland Hall, including a moon bounce, face painting, obstacle course and more. Early bird fireworks at 5:30 p.m. Downtown enjoy a DJ under the big tent 8–9 p.m., live music 9–midnight, and more fireworks to ring in the new year.

New Year's Eve Bash
Open bar, hors d’oeuvres, music, raffles, and a great view of the fireworks. Ages 21 and older. $116. 8:30 p.m. Pusser’s Caribbean Grille, Annapolis Marriott Waterfront Hotel.

Big Night DC
Fifteen themed party areas, open bars, food buffets, multiple dance floors, live music and DJs, party favors and more. $99–$329. 9 p.m.–3 a.m. Gaylord National Hotel & Resort, National Harbor.

Big Night Baltimore
Themed party areas, open bars, food buffets, multiple dance floors, live music and DJs, party favors and more. $100–$200. 9 p.m.–2 a.m. Radisson Baltimore Downtown-Inner Harbor, Baltimore.

Charm City Fireworks Cruise
Ring in the New Year on an exclusive and fun fireworks cruise aboard the luxury yacht, Raven in Baltimore’s Inner Harbor. $90. 10 p.m.–1 a.m.



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