A list of our favorite Holiday events around Annapolis, Eastern Shore and beyond for the month of December. Event dates may be subject to change.
11th Annual Lights of Kindness
The Rotary Club of South Anne Arundel County will celebrate the 11th anniversary of its Annual Lights of Kindness charity event, a Christmas tree decorating contest that will be held December 5th through 8th at Homestead Gardens in Davidsonville. This event raises thousands of dollars for local charities. Since inception, the event has raised more than $190,000 for local charities. Be sure to vote for your favorite tree at Homestead Gardens or online at rotarylightsofkindness.org.
The Nutcracker
There are plenty of opportunities to see the most classic Christmas time show: The Nutcracker. Ballet Theatre of Maryland will continue the timeless holiday tradition and sweep you away with the tale of Clara and her adventures to rescue her beloved Nutcracker from the Rat Queen’s evil spell. There will be shows December 14th through 22nd at Maryland Hall in Annapolis. Be sure to get your tickets now at balletmaryland.org.
Photo courtesy of Historic Annapolis
A Colonial Yuletide
Celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead on December 7th from 2 to 5:30 p.m. Learn about holiday traditions of colonial Annapolis from living historians as they bring these historic homes to life on this merry day. Enjoy sweet treats, games, music and crafts for the whole family. Admission includes both sites; advance registration recommended. Register and find more information at annapolis.org.
ICE! At Gaylord National
Gaylord National has a super special tradition every year: ICE! This year, see “A Charlie Brown Christmas” come to life in a dazzling, immersive, story-driven holiday showplace. More than 40 world-renowned master artisans spend more than six weeks hand-carving approximately 6,000 blocks of ice to create this one-of-a-kind Christmas attraction with 14 scenes, ice slides, and more! Get tickets at christmasatgaylordnational.marriott.com.
A Celebration of Christmas
J. Ernest Green, The Annapolis Chorale, Annapolis Chamber Orchestra, and special guests Broadway star Derrick Davis and pianist Mark Berman 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” and “Twas the Night Before Christmas.” Enjoy a joyous blend of everyone’s favorite songs at Maryland Hall in Annapolis on December 6th at 7:30 p.m. Get your tickets and sing along to all of the classics. Find more information at liveartsmd.org.
The Bluegrass Nutcracker
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 on December 20th at 7:30 in the Live Arts Studio in the Annapolis Mall. Before each movement, a zesty narrator recounts ETA Hoffman’s story while poking fun at its often-overlooked ridiculousness. The show is family-friendly and fun for lovers of Classical and Bluegrass music alike. If you are tired of canned Christmas music and want to hear something new—this is for you! Inspired by artists like Chris Thile and The Piano Guys, Front Porch Orchestra is set to revitalize all 17 movements of Pytor Tchaikovsky’s “Nutcracker”—played on banjo, violin, viola, guitar, string bass, and percussion. Get tickets at liveartsmd.org.
Midnight Madness
Everyone needs to do some last-minute shopping, so why not join Downtown Annapolis Partnership with Midnight Madness. Visit Downtown Annapolis on the first three Thursdays of December to encompass the charm and character of our most beloved town. Join other shoppers in seeing the holiday decorations, trees, garlands, and snowflakes making downtown into a winter wonderland. Several new shops can be found this year on West Street, Maryland Ave, Fleet Street, and Main Street alongside your favorite long-time businesses. The first two Thursdays will be 4 p.m. to midnight and the third will end at 11 p.m. Find more information at midnightmadnessannapolis.com.
Holiday Pops
This year, you will have two opportunities to enjoy Annapolis Symphony Orchestra’s Holiday Pops Concert. On December 13th at Maryland Hall in Annapolis and on December 14th at Severna Park High School. The evening will consist of Annapolis Symphony Orchestra and its 70 professional musicians performing all of your favorite holiday music to feel the magic of the season! Get tickets at annapolissymphony.org.
Chanukah Wonderland
Chabad of Anne Arundel County presents Chanukah Wonderland at the Annapolis Mall in the Crate and Barrel Court on December 7th at 5:30 p.m. The night will include fun and games for all ages, latkes, doughnuts, a menorah lighting, crafts, and more! RSVP for this free event at chabadaac.com.
Nutcracker Tea
What’s Up? Media’s beloved Nutcracker Tea returns on Sunday, December 1st, with seatings at 10 a.m., 2 p.m., and 5 p.m. at the Graduate Annapolis Hotel. Sip on festive tea, savor a delightful buffet, and watch as scenes from The Nutcracker come to life on stage. Plus, enjoy story time with Santa and Mrs. Claus. Visit whatsupmag.com to see if tickets are still available.
Chocolate Binge Festival
The first Sunday of December in Downtown Annapolis has a big tradition: Annapolis Chocolate Binge Festival. The Inner West Street Association brings family friendly entertainment, chocolate, holiday shopping and the festive West Street holiday Light Canopy to the first block of West Street at Church Circle from 11 a.m. to 4 p.m. Indulge in your sweet tooth, listen to music and visit Willy Wonka and the Oompa Loompa’s to kick off the holiday season! Find more information at annapolischocolatefestival.com
Military Bowl
The Go Bowling Military Bowl is the National Capital Region’s college football postseason bowl game featuring a matchup between teams from the Atlantic Coast Conference and American Athletic Conference. Played on December 28th at 5:45 p.m. at Navy-Marine Corps Memorial Stadium, the Bowl’s mission is to honor the nation’s current and former service member’s and positively impact the regional economy. Gameday kicks off with the Military Bowl Official Tailgate showcasing military displays, games and music, with food and beverage available for purchase. At the same time, the Military Bowl Parade steps off at City Dock and concludes at the stadium, featuring the world-famous Budweiser Clydesdales, Medal of Honor Recipients, pageant winners, and a variety of youth, community and military-themed groups. Proceeds from the Bowl also benefit Patriot Point, the Military Bowl Foundation’s 294-acre retreat for wounded, ill, and injured service members, their families and caregivers. Find more information and get tickets at militarybowl.org.
Holiday Market
West Annapolis Business Association is hosting their Holiday Market on December 7th from 11 a.m. to 5 p.m. at the parking lot of 20 Ridgely, at the corner of Annapolis Street and Giddings Avenue. From hot chocolate to holiday shopping and a visit with Santa Claus, you won’t want to miss this year’s Holiday Market! Find more information at west-annapolis.com.
Skate with Santa
Santa will be taking a break from his busy schedule at the North Pole to visit the Talbot County Community Center to share holiday memories with the whole family! Kids will have an opportunity to sit on Santa’s lap to reveal their seasonal wishes and receive a special gift! Please bring your own camera to take a memorable photograph with Santa. Be sure to pre-register for either December 4th or December 5th from 6 to 8 p.m. Complimentary hot chocolate and cookies will be provided. Pre-registration is required as Santa’s helpers need to maintain quantity and quality skates and gifts. Pre-register at talbotparks.com.
First Night Talbot
On December 31st, use First Night Talbot to ring in your new year with a family-friendly New Year’s Eve Celebration of the Arts in Easton! First Night Talbot has entertainment and fun for the whole family from 6 p.m. to midnight. Traditionally, events are spread out among venues in downtown Easton, culminating with the world-famous Crab Drop at midnight (and 9 p.m. for the early birds). Find more information at discovereaston.com.
SantaCon OCMD
Ocean City is turning into the North Pole on December 13th and 14th…just one catch, everyone is Santa. Just like how they started in 2011, many bars and restaurants will take place in SantaCon XIV. Walk the boardwalk and grab a cup of cheer with over 1,000 Santas to help support Ocean City charities. Find more information at santaconocmd.com.
The Merry Market Pop-Up
On December 7th from 10 a.m. to 5 p.m., Dorchester Center for the Arts will be hosting the Merry Market Pop-Up. Shop dozens of quality, hand-crafted items from local artists, enjoy live music, and holiday refreshments for all of your holiday shopping. Find more information at dorchesterarts.org.
Santa Swim
Care and Share Fund of Dorchester County is hosting The Santa Swim on December 14th. At 11 a.m., Santas will take a crisp swim in the Choptank River at the Hyatt Regency Chesapeake Resort in Cambridge. The swim raises money for The Care & Share Fund, which provides aid to individuals who have critical needs which are not able to be filled by public sources. Find more information at careandsharefund.com.
Photo by Mary Simmons
Dickens of a Christmas
Step back into 1840s London and experience the holiday season as Charles Dickens imagined it with Dickens of a Christmas. On December 6th and 7th, Main Street in Chestertown will celebrate the season with a two-day event including carriage rides, entertainment, home tours, food, book talks, merchandise, and more. Find more information and the dickens dress code at mainstreetchestertown.org.
Frosty’s Holiday Village
For All Seasons invites the whole community for an evening with Frosty! On December 6th at 5:30 p.m., visit Anchor Church in Easton for a stroll through the holiday village and free activities including professional photos with Frosty and friends, complimentary cocoa, cider, treats, and a continuous showing of “Frosty’s Winter Wonderland” on the big screen. Find more information at forallseasonsfrosty.org.
Oxford Holiday Market
The inaugural Oxford Holiday Market will bring the holiday festivities to the town of Oxford on December 13th through December 15th. The market will offer a weekend filled with unique artisan gifts, delicious food, holiday music, and special guests. There is something for everyone on your list at the market, which is held at Oxford Community Center. Find more information at talbotchamber.org
Starlight Shopping
Stroll and shop through downtown Easton as you enjoy unique holiday gifts, seasonal treats, and the festive atmosphere of historic downtown! Starting every Thursday in December and leading up to Christmas, carolers will wander the sidewalks filling the night with music, free horse carriage rides will allow you to see the town’s merry decor and charm, the Tidewater Inn will host a special pop-up bar, and unique shops will be open until 7 p.m., giving visitors the perfect opportunity to find special presents for your loved ones. Don’t miss out on this merry shopping extravaganza! Visit discovereaston.com for more details.
Tour of Homes
One of the highlights of Christmas in St. Michaels weekend is Tour of Homes. The historic homes on the tour, which are all within walking distance from each other, were built in the 18th and 19th centuries and were once homes of watermen and seafarers. Tour-goers will be able to walk through these houses, decorated for the season, on December 14th and 15th. Find more information and get tickets for the tour at christmasinstmichaels.org.
The holiday fun doesn't end here. Check out our feature on local Parades, Lights Shows & Tree Lightings.
