During the holidays, Annapolis and Anne Arundel County become a cheerful winter vacation full of historic charm, sparkling lights, and community spirit. In December, there is something for everyone, from the Grand Illumination tree lighting ceremony in Market Space that starts the season and is loved as a yearly tradition, to cozy experiences in downtown and celebrations at the waterfront.
This area has many seasonal events that celebrate the magic of the holidays as well as local culture and tradition. These include classic holiday markets, light shows that kids will love, one-of-a-kind festivals, and waterfront boat parades. Annapolis is known as one of the Mid Atlantic’s most lovely Christmas destinations due to its charming downtown streets and scenic harbor views.
Let’s know more about things to do in Annapolis MD Christmas Events with Zavros Place!
1. Grand Illumination
Annapolis’s signature holiday beginning event is the Grand Illumination. The historic Annapolis Maryland Christmas tree lighting marks the official start of the holiday season. This cherished practice is happening in 2025 from 3:00 to 5:30 PM on Sunday, November 30. It will be held near the Market House and City Dock, as it is every year, and everyone is welcome to attend without paying.
In the afternoon, the festivities start with live performances by local artists, singers, and dance groups. These performances create a mood for the community-focused event. There is a lot for people of all ages to enjoy before the main event, which is the tree lighting ceremony.
The Annapolis Symphony Academy Aquarius Wind Ensemble performs, and there are also stories and activities for kids at nearby stores. Usually, Santa, Mrs. Claus, and Elfie are there to flip the switch and light the tree.
Grand Illumination is more than just a lighting ceremony. It brings together families, residents, and tourists for an early Christmas in Annapolis Maryland experience full of music, fun food, and seasonal cheer. Grand Illumination is a loved yearly custom for the area. The city area around the event, which is already decorated with lights, turns into a bright scene where people can walk around and do Annapolis MD Christmas shopping, eat, and be entertained.
2. Midnight Madness
One of the most eagerly awaited holiday traditions in Annapolis is Midnight Madness, which combines fun late-night shopping with holiday-themed activities in the middle of historic downtown.
This annual event is hosted by the Downtown Annapolis Partnership and turns Main Street, West Street, Maryland Avenue, Market Space, and City Dock into a lively winter wonderland. Visitors come together for a memorable evening as the storefronts are lit up with holiday decorations and cheerful music plays.
Midnight Madness will happen on the first three Thursdays in December 2025. These dates are December 4, 11, and 18. On the first two nights, shops, galleries, and restaurants stay open from around 4:00 PM until midnight. They offer longer hours, special deals, and festive promotions. On the last day, which is usually called the “Eleventh Hour,” businesses that are taking part stay open until about 11:00 PM.
The event’s goal is to attract people, both locals and visitors, to enjoy the magic of the season by shopping at local stores and supporting small businesses.
In addition to vendors that are open late at night, you can also find local shops with holiday sales, restaurants with seasonal drinks and treats, street performers, carolers, and fun places to take pictures, like the Market Space Christmas tree and Snowflake Alley. Many businesses offer free drinks, making it simple to enjoy the holiday spirit on old brick-lined streets.
Midnight Madness is not only about shopping. With all the bright lights, it brings together residents, families, and visitors to enjoy one of Annapolis’s most loved holiday traditions: the community and holiday spirit. People can find unique gifts and enjoy fun holiday activities.
3. Annapolis Chocolate Binge Festival
The Annapolis Chocolate Binge Festival is a fun and sweet event that officially starts the holiday season in downtown Annapolis. This event is held every year on the first Sunday in December. It turns the first block of West Street into a cheerful place with lots of chocolate, live entertainment, and holiday shopping. It is one of the most anticipated get-togethers of the season in the city.
In 2025, the event will be on Sunday, December 7, from 11:00 AM to 4:00 PM. Under the West Street Holiday Light Canopy, hundreds of chocolate merchants sell truffles, fudge, brownies, cookies, cupcakes, chocolate-infused drinks, and inventive confections in a lively street fair ambiance.
Along with these tasty treats, local artists display their handmade goods, like jewelry, candles, gifts, and more. This makes the event a great place to start your holiday shopping while also satisfying your sweet tooth.
The event has live music and entertainment that makes the mood more festive all day, in addition to tasty food and shopping. If you love chocolate or are just looking for a fun family-friendly holiday event, the Annapolis Chocolate Binge Festival has lots of chocolate, shopping, and holiday spirit in the heart of historic downtown.
4. Annapolis Gingerbread Houses
The Great Annapolis Gingerbread Houses exhibition and contest is a lovely holiday tradition that celebrates creativity, community spirit, and festive fun. Every year, this event invites bakers, families, artists, and local groups to make creative gingerbread structures, like classic cottages or fun holiday scenes. Everything is made from edible materials and put on show for people to enjoy.
In 2025, the gingerbread houses will be open for the public to see at the Annapolis Visitors Center (26 West Street), from November 22 to December 19. It does not cost anything and does not require a ticket to enter, so people who live there or are just visiting can easily do it during the holidays.
People can vote for the first part of the display until December 7. At the Annapolis Chocolate Binge Festival, winners are revealed in several categories, including a fan favorite and cash prize awards.
The event encourages people to compete with each other in a friendly way and get involved in their community. It gives people of all ages a chance to show off how they can decorate and how creative they can be with holidays. This fun tradition makes downtown Annapolis look more charming and festive, whether you are watching the beautifully made houses or voting for your favorite.
5. Eastport Yacht Club Lights Parade
The Eastport Yacht Club Lights Parade is one of the most loved Annapolis Christmas events. It brings both residents and tourists to the shore for a memorable night of holiday cheer and fun.
Every year on the second Saturday in December, the parade is set against the winter sky as dozens of boats with thousands of bright lights and fun themes pass through Annapolis Harbor and Spa Creek. In 2025, the event will take place at 6:00 PM on Saturday, December 13, and people who watch from the beachfront will still not have to pay.
In the 1980s, members of the Eastport Yacht Club started the practice of decorating their boats and sailing around the harbor during the holiday season. This started a joyful celebration that has grown into one of the region’s most famous seasonal events.
The festive parade is a fun community event that helps local causes. The money from the parade goes to the EYC Foundation, which funds educational programs, scholarships, and sailing classes for kids.
People who are not participating can see the lights from a number of different places along the waterfront. The Spa Creek Bridge, the City Dock walkway, and the street-end parks in the Eastport neighborhood are all great places to see the water. People can see the lit-up boats up close as they pass by from the bridges or the shore. For a more unique experience, they can also watch from the water on a cruise or charter boat.
The Eastport Yacht Club Lights Parade is a wonderful way to start the holidays in Annapolis, whether you are on the docks with hot chocolate or on a rented boat watching from the water.
6. Lights on the Bay
In the Annapolis area, Lights on the Bay is a cherished holiday tradition that turns Sandy Point State Park into a beautiful winter wonderland that you can drive through along the Chesapeake Bay. This holiday light show will take place from November 23, 2025, to January 1, 2026. It features over 70 animated and non-animated displays along a two-mile scenic path with bright holiday themes and inventive designs.
Every night, people can drive through the park and enjoy the view of the bay with all the sparkling lights. Standard hours are 5:00 PM to 9:00 PM Sunday through Thursday and 5:00 PM to 10:00 PM on Fridays and Saturdays, including holidays. Cars, vans, and buses all have their own ticket prices, and you can buy 3D glasses to make the experience better by adding depth and detail.
Lights on the Bay is a fun family activity that also supports a good cause: the tickets raise money for the SPCA of Anne Arundel County, which helps animals in the neighborhood.
This event is set by the water and features a wide range of creative displays, from traditional holiday scenes to ones that are themed around Maryland. It offers a magical experience for everyone, no matter their age, and is widely thought to be one of the most important sights to see in the area during the season.
7. Annual Kwanzaa Celebration
The Annual Kwanzaa Celebration in Annapolis at Christmas is a meaningful and lively event that honors African history and culture and the Nguzo Saba, or “Seven Principles.” The celebration also brings community members together.
This celebration is different from other holiday events that are mostly about markets and lights. It focuses on culture, education, and coming together, making a space where art, tradition, and shared experiences are honored.
The 2025 Annapolis Maryland Christmas event is at the Banneker Douglass Tubman Museum (84 Franklin Street, Annapolis) on Saturday, December 13, from 10:00 AM to 4:00 PM. This museum is the official center for African American history and culture in Maryland. It is a great place to hold a public celebration, and signing up ahead of time would help with the planning.
The day will include live African and African diasporic music, dancing, and storytelling. Afrocentric food and a market with Black-owned businesses are also part of the Christmas events today. There are also workshops where people can ask questions and participate, which encourage people to think about Kwanzaa’s ideals of unity, creativity, collective responsibility, and faith.
Along with fun and food, the party often has deep conversations and activities meant to teach and inspire people of all ages. The Annapolis Kwanzaa Celebration has become an important holiday tradition for families and visitors because it focuses on national pride, community, and shared history.
8. Snowflake Alley
One of the most charming and captivating holiday displays in downtown Annapolis is Snowflake Alley. It adds a festive feel and sparkling lights to the city center. This holiday-themed feature is in Cabbage Alley, the walkway for people on foot that goes off of Main Street and is near Chick & Ruth’s Delly. It is lit up for the whole holiday season, which is usually from late November to January. It is a great place to visit while seeing the city’s other holiday attractions.
Unlike big light displays or planned shows, Snowflake Alley is not set up as its own event. Instead, it is a year-round holiday project that makes the historic downtown of Annapolis more festive. Above the narrow walkway is a magical scene made of thousands of small, snowflake-shaped lights. It’s great for evening walks, family pictures, or a short break during Midnight Madness and other fun Christmas events in Annapolis.
Snowflake Alley is in the middle of Annapolis’s downtown area, which makes it easy to combine with other holiday activities, like shopping, eating, visiting the Christmas tree in Market Space, and walking along Maryland Avenue and West Street, which are both covered in lights. This glowing alleyway adds a uniquely festive touch to Annapolis’s holiday scene, whether you are just passing through on your way to something close or visiting just to see it.
9. Annapolis Holiday Market
The Annapolis Holiday Market is one of the most fun and popular ways to shop during the season. It offers a classic holiday market experience right in the middle of old Annapolis. This outdoor Kris Kringle-style market features local and regional artists, food vendors, and performers. It creates a fun and festive setting that celebrates the holiday spirit and community craftsmanship.
In December 2025, the market will move to a new, bigger spot on the front yard of St. John’s College (60 College Ave, Annapolis, MD 21401), which is only a short walk from the downtown shops, restaurants, and waterfront. People can go to the market for free, which takes place over two weekends: Saturday, December 13 (11:00 AM–9:00 PM) and Thursday through Sunday, December 18–21 with different hours each day.
Holiday tourists can look through over 100 artist booths with handmade crafts, art, jewelry, holiday decorations, special foods, and one-of-a-kind gifts. It adds to the holiday spirit that you can often get local foods and seasonal drinks like spiced wine, apple cider, and hot chocolate at the same place.
Because the market is close to Annapolis’s old downtown, it is easy to combine with other holiday activities, like visiting the light displays, taking part in the events, and eating downtown. The Annapolis Holiday Market has quickly turned into a holiday-season must-see for both locals and tourists because of its mix of shopping, seasonal treats, and seasonal fun.
FAQs
Where can I find the best parking options for holiday events in Annapolis?
Use ParkMobile to get two free hours on city meters and make parking easier. Mills-Hillman Garage and street parking near Main Street and Market Space are popular places to park. There are also charging sites for electric vehicles and parking spaces that are easy to get to.
Are there special holiday markets, seasonal shows, or festive performances in Annapolis?
Yeah! Some of the best parts are the Annapolis Holiday Market at St. John’s College, temporary markets during Midnight Madness, and live acts like street music and carolers.
When does Snowflake Alley light up for the holiday season in Annapolis?
From early December to January, Snowflake Alley usually has lights on it. This makes downtown Annapolis look nicer.
Where can I shop in Annapolis and Anne Arundel County during the holiday season?
You can get a wide range of stores in Annapolis Mall and Arundel Mills Mall, or you can shop at one-of-a-kind businesses in downtown Annapolis. You can also find local items at the Annapolis Holiday Market.
Where can I dine in Annapolis and Anne Arundel County during the holiday season?
Annapolis has restaurants in the downtown area that serve holiday food and create a festive eating atmosphere. Annapolis Town Center and Arundel Mills have a lot of different kinds of restaurants if you want more choices.