Annapolis Christmas 2025

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 Chocolate Binge Festival

Sunday, December 7, 2025

📍 West Street

West St, Annapolis, MD 21401

(2.8 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: FREE

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Low to medium

Event Description

Get ready for a decadent celebration of all things chocolate at the Annapolis Chocolate Binge Festival! This family-friendly event transforms the first block of West Street into a chocolate lover's paradise. Alongside a delightful array of chocolate vendors, the festival hosts an exciting Gingerbread House decorating contest, inviting everyone from church groups to businesses to showcase their festive creations. It's the perfect way to kick off the holiday season with sweet treats and community spirit.

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⭐ Best For: Chocolate lovers, families, holiday shoppers

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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 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 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

Experience a unique holiday spectacle as decorated boats illuminate the waterways in a dazzling parade. This event offers a festive maritime twist on traditional light displays, showcasing creative and vibrant holiday decorations on vessels.

holiday_light_displayscommunity_celebrationseasonal_activitiesholiday_traditionfestive_decorations

⭐ Best For: Holiday light displays, family outings

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Annapolis Christmas Movies, Theater and Entertainment

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A Very JAGMAC Christmas Concert

Sunday, December 22, 2024

📍 Vibe

2072 Somerville Road, Annapolis, MD

(2.5 mi from Annapolis)

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $$

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: High

Event Description

Get ready for 'A Very JAGMAC Christmas,' a special holiday concert featuring the six-sibling pop band JAGMAC. They will be performing a mix of cover songs, unreleased music, and their popular hits like 'Wrapped Up.' Attendees can anticipate energetic performances, catchy harmonies, and impressive dance moves. Special guests Laura Brino and Pure Skies will also be joining the festive celebration.

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⭐ Best For: Families, music lovers, holiday 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.

community_celebrationfamily_friendlyfestive_foodholiday_traditionseasonal_activities

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

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Jolly Express Cruise

Saturday, November 1, 2025

📍 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

Embark on Annapolis' beloved holiday tradition, the Jolly Express Cruise. This delightful 45-minute voyage on Spa Creek offers a magical 'sleigh ride' experience complete with holiday music and warm hot cocoa. Captain Santa or Mrs. Claus will guide the festively adorned Miss Anne, creating cherished memories for all aboard. It's an ideal way to kick off the holiday season and create lasting family traditions, with a portion of proceeds supporting Historic Annapolis.

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⭐ Best For: Families, couples, holiday enthusiasts

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