Festive Annapolis Events to Ring In Christmas in Maryland

Annapolis is a waterfront town bathed in history, with a very walkable historic district and suburbs that meander outwards, providing even more opportunities for winter adventures. As the capitol of Maryland, Annapolis Events embrace the history of Christmas in Maryland, as well as some newer traditions.

Christmas Annapolis Events

Any seasonal festivities tend to be permeated with a strong sense of community pride in Maryland’s rich history and seaside economy, so don’t be surprised by some blue crab memorabilia or a few colonial ghosts popping up wherever you go. Whether you like exciting outdoor light shows or cozy musical venues, Christmas in Annapolis will have the event to start your holidays off right.

Remember, events are always subject to change. It is always a good idea to check the website and call ahead to confirm timing and any special precautions that are in place.

Winter Blooms in Historic London Town

  • Address: Historic London Town and Gardens, 839 Londontown Road, Edgewater, MD
  • Dates   November through mid-December, re-opens in mid-January
  • Website

Enjoy the stunning views of South River on a walk through ten acres of woodland and ornamental gardens. This flower-centric arboretum places its hardiest winter blossoms, like the bold white, pink, and red Camellias, front and center, for a burst of color all year long.

Other winter favorites include fragrant evergreens, beautiful holly and delicate viburnum. The grounds also give visitors a taste of history with reconstructed colonial buildings, including the Lord Mayor’s Tenement, the Carpenter Shop, and the National Historic Landmark William Brown House.

This is a popular site for school trips,with exhibits that are kid-friendly and staff happy to answer questions from students (and their parents).

Christmas Annapolis Events

Get a New View of the City with Holiday Cruises

  • Address: departs from City Dock, Annapolis, MD
  • Dates: cruises run daily throughout November & December; special holiday packages on weekends in December
  • Website

A cruise along Spa Creek past downtown Annapolis is a must for visitors any time of year, but especially during the holidays, when special tours provide an extra dose of Christmas fun.

Families should check out the Jolly Cruise Express or Captain Santa’s Cruise, both of which feature caroling, sweet treats and the big man himself at the helm! (Where does Santa find the time?)

For those who like some variety in their holiday events, try the Holiday Stroll & Cruise, which starts with a historic tour of Annapolis with a guide in period costume, explaining the colonial traditions of the holiday season. Then, visitors board the decked-out Saint Anne for a relaxing 40-minute cruise.

Of course, the standard boat rides of Annapolis are just as fun during the holidays as any time of year. For our money, the best bets are the romantic Harbor Lights evening cruise aboard the Harbor Queen, or the “Spirits & Spirits” haunted walk and booze cruise for some ghostly Dickensian fun.

Christmas Annapolis Events

Lights on the Bay for Animal Welfare

  • Address: Sandy Point State Park, 1100 East College Parkway, Annapolis, MD
  • Dates: November 20th – January 2nd, 5 – 10 PM
  • Website

Enjoy this leisurely drive along the Chesapeake Bay while enjoying more than 60 animated and stationary light displays sure to put a smile on every passenger’s face. And don’t forget to pick up 3D glasses at the beginning of the scenic tour for a little extra dose of light show magic!

The event showcases Maryland history and also has a decidedly feline and canine flavor, with all proceeds benefitting the SPCA of Anne Arundel County. In fact, for two nights in mid-November, guests can buy special tickets for the Lights & Leashes event, where dogs and their humans are permitted to park their cars and walk through the brilliant light display.

Christmas Annapolis Events

Small Business Saturday

  • Address: throughout Annapolis and Anne Arundel County
  • Dates: Saturday after Thanksgiving
  • Website

Downtown Annapolis takes its small businesses seriously, and hosts special events such as Small Business Saturday to make sure local shop owners thrive.

Free parking is available all day, and the website gives a complete list of independent shops and what you can find there. We never miss a chance to pop into the HERE. A Pop Up Shop, to see what the owner has found (most from artists and makers!) that we just have to have.

Show Annapolis businesses that you appreciate their personalized attention, unique offerings and community spirit by patronizing them all day. It’s a great way to find one-of-a-kind gifts for everyone on your Christmas list!

Christmas Annapolis Events

Artist Sunday

  • Address: throughout Annapolis and Anne Arundel County
  • Dates: the Sunday after Thanksgiving
  • Website

Why not follow up Small Business Saturday with a new tradition celebrating independent artists and creators of every stripe? Annapolis takes an active role in this national festivity, with its multitude of art stores, galleries and performance venues.

Check the annual Facebook event page or the website of your favorite Maryland art space for a number of discounts and special events going on throughout the region.

Homestead for the Holidays

  • Address: 743 West Central Avenue, Davidsonville
  • Dates: throughout December: live music on weekends through December 20, 2020
  • Website

Enter a truly enchanted wonderland with this home decor store, nursery and greenhouse as it is decked out with dozens of beautiful Christmas trees of every size and shape, thousands of ornaments, innumerable lights, and everything you could need to make your own holiday scene.

For the 30th year, Homestead’s famous railroad will chug around the greenhouse as guests enjoy a hot chocolate and watch elves hard at work in Santa’s workshop. Live music and talking reindeer delight kids of all ages.

In the outside nursery, a fire pit roars as families pick out their own fragrant evergreens

Parade of Light—Car Parade & Menorah Lighting

  • Address: Safeway parking lot, 2635 Housley Road, Annapolis, MD
  • Dates: Sunday, December 13, 2020, 5:30 PM
  • Website

Chabad Anne Arundel County has entertaining events scheduled throughout Chanukah, but our favorite is the annual Menorah Car Parade on the fourth night of the Festival of Lights. All are welcome to join and even participate in the parade!

Participants should pull up by 5 PM to leave from Safeway, and drive to the Alex Haley Memorial with fun menorah decorations on their roofs. At 5:45 PM, event organizers will kindle a giant Menorah and celebrate the miraculous holiday.

Drivers and spectators will receive chocolate gelt (coins), prepackaged latkes, and kits to help celebrate Chanukah, while supplies last.

Annual Kwanzaa Celebration

  • Address: Banneker-Douglass Museum, 84 Franklin Street, Annapolis (For 2020, completely virtual)
  • Dates: Friday, December 11, 2020, 12 to 2 PM
  • Website

This program is perfect whether you’re a long-time Kwanzaa celebrant or want to learn more about the African-American seven-day festival. Honor the seven principles of Kwanzaa through musical and spoken word performance, a lighting ceremony, an interactive gift-making session, and a discussion on the importance of community and intergenerational engagement.

Also featured is a Buy Black Marketplace where you can find one-of-a-kind artisanal home goods, art and gifts. 

NOTE: For 2020, the candles of Kwanzaa will be lit virtually, with all the same beloved events and the marketplace moving online. Registration is free through the website.

Christmas Annapolis Events
Snowflake Alley/ credit Visit Annapolis

Midnight Madness Holiday Shopping

  • Address: throughout downtown Annapolis
  • Dates: The first three Thursdays in December—first two, 4 PM to midnight; third, 4 PM to 11 PM
  • Website

On these special nights, the town is transformed into a winter wonderland as shops stay open late for shoppers in need of that perfect gift and who want to support local businesses.

The event takes place along Main and West Streets, Maryland Avenue, State Circle and Dock Street, and pedestrians looking for deals or simply enjoying the lovely night are treated to live outdoor music, refreshments and other entertainment (most of these crowd-drawing activities will be suspended in 2020).

Make sure not to mis Snowflake Alley, the holiday lights canopy, and of course the city Christmas tree at Market Space.

Christmas Annapolis Events
credit Sabrina Raymond

Holiday Candlelight Stroll

  • Address: departs from Market House Park, Annapolis
  • Dates: Fridays and Saturdays in December, 7 – 9 PM
  • Website

A guide in festive period attire leads guests along the centuries-old brick lined streets of Maryland’s capital city, lit by lanterns and candles and lavishly adorned for the holidays. Visitors will be enchanted by charming and humorous stories of 18th and 19th century holiday traditions against the backdrop of colonial mansions, Victorian homes, and quaint shops.

Christmas Annapolis Events
credit Visit Annapolis

First Sunday Arts Holiday Market

  • Address: Whitmore Park, and West Street between Church Circle & Graduate Annapolis Hotel, Annapolis
  • Dates: First Sunday of each month: special holiday markets November 1 & December 6, 2020
  • Website

The city provides free parking for this cherished Annapolis event, so that shoppers can leisurely browse the creations of over 50 local and regional artisans in search of quirky and unique gifts for friends and family.

Diverse artists and booths offer everything from customize portraits and delicious-smelling candles to Christmas ornaments with a Maryland flair (plus, visit over a hundred more artists virtually on their website!).

Outdoor café seating and live music is provided for shoppers who need to take a break, and it’s also a perfect day to visit the galleries and art shops of West Street, many of whom take part in the market with special events and deals.

A Celebration of Christmas 

  • Address: Friday, December 11, 2020, 8:00 PM
  • Dates: Online, Maryland Hall, and possibly other locations
  • Website

Each year, tickets sell out early for this enthralling evening, in which The Annapolis Chorale and Chamber Orchestra join together to perform dozens of seasonal favorites to standing ovations in a one-night only show.

Because the Annapolis Chorale cannot all share one stage this year, the organization plans to live stream performances from all over town that individuals can enjoy at home, with the possibility of limited in-person seating as well. Keep checking their website for further details.

Christmas Annapolis Events
credit Visit Annapolis

Ballet Theatre of Maryland presents The Nutcracker 

  • Address: Online and outside Gordon Biersch, 1906 Towne Centre Blvd, Annapolis
  • Dates: December 12-13 and 19-20, 2020
  • Website

This cherished holiday tale of a girl’s adventure alongside her unusual Christmas present is performed by the top-tier dancers of the prestigious Ballet Theatre of Maryland. Let the spell-binding music of Tchaikovsky and the athletic dancers whisk you away to the whirling Kingdoms of Snow and Sweets.

For 2020, the entire show can be streamed live right to your home, or there will be a live stream on a drive-in big screen at Annapolis Town Center. Visitors can watch from the safety and comfort of their cars, and will receive their own Nutcracker ornaments!

Handel’s Messiah—Reimagined 

  • Address: St. Anne’s Episcopal Church, Church Circle, Annapolis
  • Dates: December 17-19, 2020
  • Website

Live Arts Maryland is determined to present one of the world’s best loved and most popular musical works, performed many times each Christmas since its completion in 1741, so the organization has reimagined how the work is performed.

The Annapolis Chorale will present the masterpiece via three performances with very limited seating. A limited number of performers will sing, and the singers will rotate from performance to performance. Each concert will conclude with carols for the season.

It will be a unique opportunity to see this moving work performed in a much more intimate venue than is typical in other years.

Annapolis Symphony Orchestra – Holiday Classics Concert

  • Address: The Music Center at Strathmore, Bethesda (For 2020, completely virtual)
  • Dates: December 18, 2020 at 8 PM
  • Website

Enjoy a concert that will warm your heart on a cold winter’s night with holiday favorites and classical selections. As part of the 2020-21 Masterworks Series, Harmony In Nature and Holiday Classics with Music Director José-Luis Novo, listeners are treated to a pre-concert talk about the histories and entertaining stories of the composers, then enjoy the highest quality musicians taking on the classics. 

For 2020, attendees will be emailed a link for the live streamed performance the day of the event.

Historic Annapolis Holiday Wreath and Gift Sale

  • Address: 1 Martin Street, Annapolis
  • Dates: order November 6 – November 18 (or while supplies last), pick up November 20 – 21. Some packages available through December
  • Website

Place your orders early for festive holiday greens, tabletop trees, a special hand-painted ornament for each year, and a curated selection of pre-wrapped gifts with a touch of Maryland charm.

Each wreath and tree is made by Historic Annapolis volunteers using greenery and plants from the William Paca Garden. Purchases benefit Historic Annapolis’ ongoing mission of education and preservation of the area’s colorful past.

Christmas Annapolis Events
credit Visit Annapolis

Military Bowl

  • Address: Navy-Marine Corps Memorial Stadium, 550 Taylor Ave, Annapolis
  • Dates: December 28, 2020, 2:30 PM kick-off
  • Website

For some, it’s a winter tradition as cherished as Thanksgiving or Christmas- The Military Bowl, benefitting the USO of Metropolitan Washington-Baltimore, pits two college football teams head-to-head: Atlantic Coast Conference against American Athletic Conference, in an outstanding display of athleticism and spirit.

The fun begins before the kickoff, with a parade through historic downtown (held virtually for 2020), featuring musical acts, civic and youth groups, and the world-famous Budweiser Clydesdales. Then, grab some concessions and take your seat for an energetic game sprinkled with special events to salute the military and their families.

Christmas Annapolis Events
credit Visit Annapolis

• • • ANNUAL EVENTS CANCELLED IN 2020 • • •

The Grand Illumination

  • Address: city docks near the Market House, Market Space, Annapolis
  • Dates: the Sunday after Thanksgiving, 5:30 PM (NOTE: lighting ceremony is cancelled for 2020, but the Christmas tree and decorations will be up all season)
  • Website

Annapolis makes a big party out of the annual lighting of the city’s Christmas tree, with a show of carols and dancing, warm drinks and candy canes, and the arrival of Santa Claus to light the tree himself!

There is plenty of fun for children, including ornaments that they can decorate. The Annapolis Jaycees will be on site, collecting toys and non-perishable foods to donate to families in need. 

Colonial Annapolis Holiday

  • Address: William Paca House and Garden, 186 Prince George Street, Annapolis
  • Dates: Weekends throughout the holiday season. (The House is closed until March 2021.)
  • Website

Always a fun trip for visitors and residents, this Georgian red-brick mansion is preserved as it would have been in the 18th century, when Paca signed the Declaration of Independence and became Maryland’s third governor.

During the holidays, celebrate the season as William, Mary, and the household servants decorate the home and prepare for a traditional colonial Christmas.

With reservations, a docent will lead you through the first floor of the house and the 2-acre William Paca Garden, while a virtual tour of the rest of the house is available.

The last guided tour departs at 2:00 PM; self-guided tours of the garden can arrive by 3:30 PM.

Christmas Annapolis Events
credit Visit Annapolis

Eastport Yacht Club Lights Parade 

  • Address: Annapolis Harbor and Spa Creek, Annapolis waterfront
  • Dates: Second Saturday in December, 6 – 8 PM
  • Website

Spectators gather each year to watch more than 30 brightly lit boats bedecked for the holiday season appear suddenly in the night and parade around the Annapolis waterfront during this beloved annual event. Thousands of lights in some very creative displays, stalwart dedicated crews, and a crowd of jolly revelers make this a fun Christmas tradition for the entire family.

Inside tip: if you bring some non-perishable food to donate, you can get onto the Harbor Queen cruise ship for free to watch the show in style!

Dining with the Loockermans

The curator and food historian of this William Buckland-built estate discuss the cooking and dining traditions of the house’s 19th century residents, both free and enslaved.

Visitors are able to savor some historically accurate treats during the hour-long tour through the stately home’s kitchen, breakfast area and dining room. Reservations are required, and often visitors can pick a daytime tour or one later in the day by candlelight.

Jane Austen Tour

The book-lover in your group will adore this spotlight tour of the historic, Christmas-decorated Hammond-Harwood House, which compares the customs and social graces of the Loockerman family, residents of the red-brick mansion during the early 19th century, with those in Jane Austen’s novels.

It’s a surprisingly affordable way to spend a holiday afternoon feeling posh and proper.

Christmas Annapolis Events
credit Visit Annapolis

Lights Parade Dinner & Dessert Cruise

  • Address: begins at Severn Inn, 1993 Baltimore Annapolis Blvd., Annapolis
  • Dates: mid-December, check website for details
  • Website

Dine in style at the Severn Inn before enjoying a dessert aboard Watermark’s luxury yacht, Catherine Marie, as you watch the spectacular annual Eastport Yacht Club Lights Parade on the water. The yacht has two levels, with double the bar service and convenient, buffet-style desserts, so your family can appreciate the parade in comfort.

Tickets include a starter, entrée, dessert, and glass of champagne, as well as the inn and cruise experience.

Winter Flowers from Around the World

  • Address: Hammond-Harwood House, 19 Maryland Avenue, Annapolis   
  • Dates: mid-November through December, open 12 PM – 5 PM except Tuesdays
  • Website

This historical 18th century estate, a must-see stop on any tour of Annapolis that never fails to please, has a current exhibition about Decadent Décor: Global Imports in an Early American Port City, which highlights the furnishings and goods that early Annapolis residents imported from around the world.

To supplement this theme, the gorgeous gardens around the mansion are adorned with floral displays inspired by flowers that bloom around the world in winter, including snowdrops, English primrose, winter jasmine, and holly. Created by local garden clubs, the displays add to the refined colonial splendor of the site as a whole and make for a lovely winter scene.

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