Annapolis Christmas 2025

Annapolis Christmas Markets and Shopping

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Midnight Madness

📍 Downtown Annapolis

Main St, Annapolis, MD 21401

(0.1 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Step into a festive Downtown Annapolis Winter Wonderland during Midnight Madness. This cherished holiday tradition invites you to stroll through streets adorned with twinkling lights, festive decorations, and a towering Christmas tree. Enjoy extended shopping hours until midnight, discover unique gifts from local boutiques, and soak in the magical atmosphere with live entertainment and carolers.

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⭐ Best For: Holiday shopping and festive atmosphere

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Annapolis Chocolate Binge Festival

Sunday, December 7, 2025

📍 West Street

(0.4 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Get ready to satisfy your sweet tooth at the Annapolis Chocolate Binge Festival! This delightful event features a chocolate tour with over 40 vendors offering everything from truffles and cakes to chocolate martinis. Browse a festive holiday market for unique handmade gifts from local artisans, and enjoy live entertainment as the West Street Holiday Light Canopy illuminates the evening. It's the perfect way to kick off the holiday season with family-friendly fun.

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⭐ Best For: Chocolate lovers and holiday shoppers

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Annapolis First Sunday Arts Holiday Market

Sunday, November 2, 2025

📍 Inner West Street

60 West Street, Annapolis, MD 21401

(0.2 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Discover the Annapolis First Sunday Arts Holiday Market, a festive gathering on historic West Street. Browse over 100 artisan vendors showcasing handmade pottery, jewelry, paintings, and more. Enjoy live music from local artists and savor delicious treats from food vendors. It's the perfect destination for unique holiday shopping and a vibrant community experience.

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⭐ Best For: Holiday shopping and artisan crafts

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Annapolis Holiday Market

Thursday, December 12, 2024

📍 Annapolis Holiday Market

1 Dock Street, Annapolis, MD 21401

(0.4 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Experience the charm of the Annapolis Holiday Market, a festive tradition set on the historic waterfront. Browse over 100 artisan and specialty food vendors offering unique handmade gifts and delicious seasonal treats. Immerse yourself in the Charles Dickens-inspired holiday atmosphere of downtown Annapolis, beautifully decorated for the season.

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⭐ Best For: Holiday shopping, family outings, festive atmosphere

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Annapolis Christmas Food, Drink and Parties

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New Year's Eve Annapolis Yacht Party

Tuesday, December 31, 2024

📍 Annapolis City Dock

1 Dock Street, Annapolis, MD 21401

(0.4 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $$$

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: High

Event Description

Ring in the New Year with an unforgettable celebration on the water in Annapolis. This exclusive yacht party offers a DJ, dancing, and a complimentary beverage, all while providing a front-row seat to the city's 9:00 PM fireworks display. Alcoholic and non-alcoholic drinks are available for purchase from the full-service bar. This event is for guests 21 and older.

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⭐ Best For: Adults celebrating new year's eve

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Annapolis Christmas Light Displays

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Eastport Yacht Club Lights Parade

📍 Eastport Yacht Club

(0.7 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Low

Event Description

Prepare to be mesmerized by the Eastport Yacht Club Lights Parade, where decorated boats transform the waterways into a shimmering holiday wonderland. This event showcases the creativity and festive spirit of the boating community as they illuminate their vessels with dazzling lights for all to enjoy.

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⭐ Best For: Families, couples, boat enthusiasts

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Annapolis Other Christmas Activities

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Grand Illumination Tree Lighting

📍 Market House

(0.3 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Join the festive kickoff to the holiday season in downtown Annapolis at the Grand Illumination. This beloved annual tree lighting ceremony near the Market House features a delightful afternoon of carols, music, and performances by local groups. Santa, Mrs. Claus, and Elfie will be on hand to light the Christmas tree, bringing holiday cheer to all.

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⭐ Best For: Families and community members

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A Budweiser Clydesdale Miracle on West Street

📍 West Street

(0.4 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Get ready for a magical evening at 'A Budweiser Clydesdale Miracle on West Street,' a festive prelude to the Military Bowl. This event features the renowned Budweiser Clydesdales, alongside a vibrant street scene with food trucks, vendors, and engaging activities for all ages. It's the perfect way to kick off the holiday spirit.

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⭐ Best For: Families, couples, and anyone looking for a festive holiday experience.

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Jolly Express Cruise

Friday, November 22, 2024

📍 Annapolis City Dock

1 Dock St, Annapolis, MD 21401

(0.4 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $$

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Low

Event Description

Set sail on Annapolis' beloved Jolly Express Cruise for a magical holiday experience. This festive 45-minute voyage aboard the Miss Anne offers hot cocoa, cheerful holiday music, and a chance to create cherished family traditions. Captain Santa or Mrs. Claus will guide the way on Spa Creek, ensuring a memorable journey filled with good cheer. A portion of proceeds benefits Historic Annapolis, making your celebration a gift to the community.

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⭐ Best For: Families and couples seeking a festive holiday experience.

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