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Family-Friendly Holiday Events in Annapolis for 2025

Christmas tree and lights in Annapolis, MD

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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If you’re searching for the best brunch in Annapolis, you’re definitely not alone. From waterfront cafés and cozy bakeries to upscale brunch spots with crab-inspired dishes, Annapolis, Maryland has become one of the best places in the region for breakfast and brunch lovers alike. Whether you’re planning a relaxing weekend outing, grabbing breakfast before exploring downtown, or fueling up before a road trip across Maryland, this guide highlights some of the top local spots for the best breakfast in Annapolis MD and brunch experiences worth trying. Why Annapolis Is a Great Brunch Destination Known for its historic charm, walkable downtown, and waterfront views, Annapolis offers a brunch scene that blends classic Maryland flavors with modern favorites. Visitors and locals alike can enjoy everything from crab omelets and homemade pastries to gourmet coffee and creative brunch cocktails. One of the best things about brunch in Annapolis is the variety. Whether you want a quick casual breakfast or a full sit-down brunch experience, there’s something for every style and appetite. more Best Brunch in Annapolis, MD: Local Favorites 1. Iron Rooster A staple in downtown Annapolis, Iron Rooster is famous for its all-day breakfast menu, homemade pop tarts, chicken and waffles, and Southern-inspired comfort food. If you’re looking for a fun, casual brunch atmosphere with generous portions, this is one of the most popular choices in town. 2. Miss Shirley’s Cafe Miss Shirley's Cafe consistently ranks among the best brunch destinations in Maryland. Known for creative brunch dishes and locally inspired flavors, their menu includes seafood omelets, stuffed French toast, and specialty pancakes that keep visitors coming back. 3. Light House Bistro For those seeking a more relaxed neighborhood feel, Light House Bistro is a local favorite. This charming breakfast and brunch spot offers fresh ingredients, vegetarian-friendly options, and excellent coffee in a welcoming atmosphere. 4. Bread and Butter Kitchen Bread and Butter Kitchen is a great option if you enjoy locally sourced ingredients and a laid-back waterfront setting. Popular menu items include breakfast sandwiches, avocado toast, crab hash, and seasonal specials. 5. Preserve For a slightly more upscale brunch experience, Preserve offers creative Southern-inspired dishes with bold flavors and a unique menu that stands out from traditional brunch spots. Best Breakfast in Annapolis MD for Early Risers Not every breakfast outing needs to turn into a full brunch event. If you’re simply searching for the best Annapolis breakfast, several local cafés and breakfast restaurants offer excellent options for a quick and satisfying start to the day. Popular breakfast choices around Annapolis include: Fresh-made bagels and breakfast sandwiches Maryland-style crab omelets Homemade pancakes and waffles Specialty coffee and espresso drinks Healthy smoothie bowls and avocado toast Traditional diner breakfasts with eggs, bacon, and hash browns Many local restaurants also offer outdoor seating during the warmer months, making breakfast in Annapolis especially enjoyable during spring and summer. Exploring Annapolis After Brunch One of the best parts about brunch in Annapolis is what comes after. The city is filled with attractions and scenic destinations perfect for spending the day nearby. After breakfast or brunch, many visitors enjoy: Walking through historic downtown Annapolis Exploring local boutiques and shops Visiting the waterfront and harbor area Touring the United States Naval Academy Taking a boat tour or enjoying Chesapeake Bay views Attending seasonal festivals and local events Planning a Weekend Drive Around Annapolis? If you’re exploring the area for brunch, shopping, or a weekend getaway, having the right vehicle can make every drive more enjoyable. At Fitzgerald Kia of Annapolis, drivers can explore a wide selection of new and pre-owned Kia models designed for commuting, family travel, and weekend adventures around Maryland. Whether you’re heading downtown for breakfast or taking a scenic drive along the Chesapeake Bay, vehicles like the Kia Telluride, Kia Sportage, and Kia K5 offer comfort, technology, and efficiency for every type of trip. Final Thoughts on the Best Brunch in Annapolis Finding the best brunch in Annapolis MD really comes down to the kind of experience you want. From classic breakfast diners and waterfront cafés to elevated brunch destinations with creative menus, Annapolis offers something for everyone. Whether you’re a local resident or visiting Maryland for the weekend, brunch in Annapolis is one of the best ways to experience the city’s food culture, charm, and hospitality.