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Upcoming Events

There's always something going on around town, and this is the place to find out!

Dec. 16, 2025 9:00 p.m. - 11:00 p.m.

Damiano David at Fillmore Silver Spring

The Fillmore Silver Spring

Concerts & Live Music

Dive into the beating heart of electronic dance music (EDM) and techno at The Fillmore Silver Spring in Silver Spring, Maryland on Tuesday 16th December 2025! Become one with the rhythmic pulse of house music, the relentless energy of techno, and... Read more

The Fillmore Silver Spring

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Dec. 17, 2025 5:00 p.m. - 7:00 p.m.

Ugly Sweater Happy Hour at Captain's Daughter Bar & Lounge

Captain's Daughter Bar & Lounge

Food & Drink

Captain’s Daughter Bar & Lounge invites guests to get into the holiday spirit at its Ugly Sweater Happy Hour on Wednesday, December 17, 2025, from 5 PM to 7 PM. Celebrate the season with $7 draft beers, $10 orange crushes, $13 crab dip, $10 flatb... Read more

Marriott International

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Dec. 17, 2025 7:30 p.m. - 10:00 p.m.

BSO Presents Classical Christmas

Joseph Meyerhoff Symphony Hall

Concerts & Live Music

Conductor Patrick Quigley leads a program featuring Charpentier’s Prelude from Te Deum (ed. Quigley), Mozart’s Exsultate, jubilate, Bach’s Orchestral Suite No. 4, and excerpts from Handel’s Messiah. Features Maya Kherani (soprano), James Reese (t... Read more

Handel Choir of Baltimore, Missa Musicians

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Dec. 18, 2025 8:00 a.m.

Midnight Madness

Downtown Annapolis

Seasonal & Holiday

Downtown Annapolis Partnership proudly presents Midnight Madness—a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the stree... Read more

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Dec. 18, 2025 11:00 a.m.

Annapolis Holiday Market

St. John's College

Art & Galleries, Fairs & Carnivals, Special Attractions

Annapolis Holiday Market expands to 2 weekends in December. This year, the holiday market will be on the front lawn of St John's College, near the intersection of College Avenue and St John's Street. This puts the market about a block from the C... Read more

Annapolis Holiday Market

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Dec. 18, 2025 noon - 1:00 p.m.

Yin and Peaceful Yoga in Downtown Annapolis

17 Francis St

Health & Wellness

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Dec. 18, 2025 2:00 p.m. - 4:00 p.m.

Flowerpot Snack n' Paint Xperience

Easton Visitor's Center

Art & Galleries

Jennifer Hartfield

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Dec. 18, 2025 6:00 p.m. - 8:00 p.m.

Brampton 1860's Grape Expectations Dinner Party

Brampton Inn

Food & Drink

Grape Expectations: A Playful Plates Party” at Brampton 1860 At Brampton 1860, we invite you to Celebrate the season with “Joyeux Feast-ivités”—a festive French holiday dinner where each small plate course is artfully paired with exceptional F... Read more

Kar-Tr

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Dec. 19, 2025 - Dec. 23, 2025

Thyme for Cheer

Harvest Thyme Tavern

Food & Drink, Seasonal & Holiday

THYME FOR CHEER: FESTIVE HOLIDAY BRUNCH & DINNER MENUS Gather your crew and soak up the holiday spirit! Chef Rik and his Team are serving up festive brunches and dinners made from scratch with the best local ingredients, perfect for lively gathering Read more

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Dec. 19, 2025 10:00 a.m. - 8:30 p.m.

THE POLAR EXPRESS™ Train Ride

B&O Railroad Museum

Fairs & Carnivals, Kids & Family, Seasonal & Holiday

Whether you’re starting a family tradition, planning a festive date night, or celebrating with friends, THE POLAR EXPRESS™ Train Ride brings the spirit of Christmas to life—for all who believe. Your adventure includes live performances, hot choco... Read more

polar-express-train-ride_31140751715_o (1).jpg

B&O Railroad Museum

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Dec. 19, 2025 11:00 a.m.

Annapolis Holiday Market

St. John's College

Art & Galleries, Fairs & Carnivals, Special Attractions

Annapolis Holiday Market

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Dec. 19, 2025 7:00 p.m. - 9:15 p.m.

The Talent Machine Presents "A Merry Mix-Up" Holiday Spectacular!

Indian Creek School

Kids & Family, Performing Arts & Dance, Seasonal & Holiday

Don’t miss The Talent Machine Company’s annual Holiday Spectacular, Dec. 12 through 23! Evening and matinee performances available! This year’s show – A Merry Mix-Up – promises to be an exciting experience for kids of all ages, with all of your f... Read more

Rich Osikowicz

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Dec. 19, 2025 7:00 p.m. - 10:00 p.m.

Bluegrass Nutcracker 2025 LIVE at Cult

Cult Classic Brewing Company

Concerts & Live Music, Food & Drink

Experience Tchaikovsky’s Christmas classic like never before! The Bluegrass Nutcracker features a bar-for-bar rendition of The Nutcracker played by an 8-piece bluegrass band. Before each movement, a zesty narrator recounts ETA Hoffman’s story whi... Read more

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Dec. 19, 2025 7:00 p.m. - midnight

Ugly Sweater Party

Live! Casino & Hotel

Nightlife & Entertainment

Join us for our trivia & ugly sweater party with a DJ, contests, awesome prizes and extended happy hour until 9PM! Location: Sports & Social Event Details: ‣ Trivia | 7:00 - 8:30PM ‣ Ugly Sweater Contest | 10:30PM Read more

Live! Casino and Hotel Maryland

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Dec. 19, 2025 7:30 p.m. - 9:30 p.m.

A CHRISTMAS CAROL RETURNS TO CHURCH HILL THEATRE

Church Hill Theatre

Kids & Family, Performing Arts & Dance, Seasonal & Holiday

What began as a radio presentation during Covid has blossomed into a beloved holiday tradition. Church Hill Theatre is delighted to bring the Charles Dickens classic, A Christmas Carol, to Delmarva audiences in December. This year directed by Kat... Read more

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Dec. 19, 2025 - Dec. 21, 2025

ASO’S Annual Holiday Pops concert

Maryland Hall

Concerts & Live Music, Seasonal & Holiday

Get ready to experience one of the most beloved traditions in Annapolis—the ASO’S Annual Holiday Pops concert! This festive season, join the Annapolis Symphony Orchestra and our 70 world-class musicians as we bring the joy, beauty, and warmth of the Read more

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Dec. 20, 2025 7:00 a.m. - 8:00 a.m.

Saturday Sunrise Yoga in Annapolis

17 Francis St

Health & Wellness

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Dec. 20, 2025 10:00 a.m. - 3:00 p.m.

Holiday Brunch with Santa at David’s™

Live! Casino & Hotel

Kids & Family

Celebrate the most wonderful time of the year at David’s™! Join us for an unforgettable Holiday Brunch with Santa, where delicious flavors and festive cheer come together to create magical memories for the whole family. What to Expect: • Lavish... Read more

Live!

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Dec. 20, 2025 10:00 a.m. - 8:30 p.m.

THE POLAR EXPRESS™ Train Ride

B&O Railroad Museum

Fairs & Carnivals, Kids & Family, Seasonal & Holiday

B&O Railroad Museum

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Dec. 20, 2025 11:00 a.m.

Annapolis Holiday Market

St. John's College

Art & Galleries, Fairs & Carnivals, Special Attractions

Annapolis Holiday Market

{"name": "Annapolis Holiday Market", "startDate": "2025-12-20T11:00:00", "endDate": "2025-12-20T11:00:00", "image": "https://whatsupmag.com/downloads/88844/download/587437255_829337343356515_8651198118599063667_n.jpg?cb=1ca819af6a2af9627dc54753accbd4ae", "@context": "http://schema.org", "location": {"address": "60 College Ave., Annapolis, Maryland 21401", "geo": {"longitude": "-76.491971", "latitude": "38.979434", "@type": "GeoCoordinates"}, "name": "St. John's College", "url": "https://whatsupmag.com/locations/md-annapolis-st-john-s-college/", "@type": "Place"}, "description": "Annapolis Holiday Market expands to 2 weekends in December.\nThis year, the holiday market will be on the front lawn of St John's College, near the intersection of College Avenue and St John's Street. This puts the market about a block from the C...", "url": "https://whatsupmag.com/events/annapolis-holiday-market-0/?occ_dtstart=2025-12-20T11:00", "@type": "Event"}

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