Looking for fun family-friendly holiday events in Annapolis? The holiday season in Annapolis is always special, and 2025 offers a full lineup of family-friendly traditions, festive displays, and community celebrations. Whether you’re planning cozy evenings, waterfront adventures, or downtown shopping nights, there are plenty of memorable events to enjoy throughout December.
As a local dealership that proudly serves families across Anne Arundel County, Fitzgerald Kia Annapolis is excited to highlight some of the best holiday activities happening right here in our community.
Lights on the Bay at Sandy Point State Park
📅 November 23, 2025 – January 1, 2026
This drive-through attraction is one of Annapolis’s most iconic holiday events. Lights on the Bay features a two-mile route filled with glowing holiday scenes, animated displays, and themed exhibits. Families can enjoy the show from the warmth and comfort of their vehicle—perfect for a relaxing evening outing.
If you’re planning multiple holiday drives this season, it’s a great time to ensure your vehicle is ready for winter. Seasonal service appointments are always available at Fitzgerald Kia Annapolis.
Eastport Yacht Club Lights Parade
📅 December 13, 2025
The Eastport Yacht Club Lights Parade transforms the Annapolis waterfront into a floating festival of lights. Dozens of decorated boats sail through the harbor, creating a spectacular event that draws residents and visitors alike. It’s a great outdoor activity for families who want to experience Annapolis’s maritime charm during the holidays.
Midnight Madness in Downtown Annapolis
📅 December 4 & 11
A beloved Annapolis shopping tradition, Midnight Madness brings extended store hours, festive decorations, and a lively atmosphere to the historic downtown district. With garland-lined streets, holiday sales, and plenty of dining options, it’s an enjoyable night out for families looking to support local businesses while embracing holiday cheer.
Annapolis Chocolate Binge Festival
📅 December 7, 2025
This sweet celebration takes over West Street with chocolate vendors, tasting booths, entertainment, and family activities. The Annapolis Chocolate Binge Festival is a favorite among locals and includes the lighting of the Holiday Light Canopy—one of the most photographed holiday displays in the city.
Annapolis Gingerbread Houses Display
📅 November 22 – December 19, 2025
The annual Gingerbread Houses Display showcases intricate creations from local bakers, artists, and community groups. This indoor event is ideal for families looking for an easy, weatherproof activity. The creativity on display makes it a fun stop for kids and adults alike.
Snowflake Alley
Located in downtown Annapolis, Snowflake Alley features sparkling lights, seasonal décor, and plenty of photo-ready moments. It’s a quick, festive stop that pairs perfectly with holiday shopping or a stroll through historic Annapolis.
More Family-Friendly Holiday Events Around Annapolis
Annapolis Maritime Museum & Park
The museum offers hands-on exhibits, maritime education, and occasional seasonal crafts for children. It’s an engaging option for families wanting something educational and interactive.
Historic Annapolis Sites
The William Paca House and Garden, among other historic landmarks, offers a glimpse into 18th-century Annapolis. During the holidays, many historic sites incorporate traditional décor, adding an extra touch of charm.
Enjoy the Holidays With Fitzgerald Kia Annapolis
From light displays to festive waterfront events, Annapolis is full of ways to celebrate the season. Wherever your holiday plans take you, having a reliable vehicle helps make the season easier, safer, and more enjoyable for the whole family.
If you’re preparing for winter travel or considering upgrading your current vehicle, browse our:
From the entire team at Fitzgerald Kia Annapolis, we wish you a safe, happy, and memorable holiday season!
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Warranties include 10-year/100,000-mile powertrain and 5-year/60,000-mile basic. All warranties and roadside assistance are limited. See retailer for warranty details.