There’s something about December in Annapolis and Anne Arundel—twinkling lights reflecting off the Chesapeake Bay, crisp waterfront air, and festive traditions that feel straight out of a holiday movie. From charming downtown streets to sparkling harbor parades, this coastal corner of Maryland is officially one of America’s most magical holiday destinations.

 

Midnight Madness – December 4, 11, and 18 🛍️

Downtown Annapolis comes alive during Midnight Madness, with historic brick streets glowing under twinkling lights. Highlights include:

  • Extended store hours and exclusive deals from local boutiques

  • Carolers serenading your holiday shopping stroll

  • Complimentary treats and festive surprises around every corner

  • Visitors Center fun from 5–8 p.m., including gingerbread house displays and s’mores

Perfect for checking off your gift list while enjoying the historic waterfront charm! Wondering what else to expect?

📍 Location: Downtown Annapolis, MD

 

Annapolis Gingerbread Houses – Through December 19 🍭

The Annapolis Gingerbread Houses Contest turns the Visitors Center into a sweet winter wonderland. Key dates:

  • Entries on display since November 22

  • Public voting open through December 7

  • Winners announced at the Annapolis Chocolate Binge Festival

From whimsical cottages to candy-laden trains, this is a feast for the eyes (and your camera roll!).

📍 Location: 26 West Street, Annapolis, MD

 

Annapolis Chocolate Binge Festival – December 7 🍫

Chocolate lovers, rejoice! West Street is your holiday playground:

  • Artisan chocolate vendors & live entertainment

  • Hot cocoa for sipping by the glow of festive lights

  • Gingerbread decorating contests and holiday photo ops

  • Sunset grand illumination of West Street

Family-friendly and decadently sweet—this is the ultimate winter treat.

📍 Location: West Street, Annapolis, MD

 

Annapolis Holiday Market – December 13 & 18–21 🎄

Step into a winter wonderland at the Annapolis Holiday Market, set against the charming backdrop of St. John’s College. Highlights include:

  • 100+ local artisans with handmade gifts and unique treasures

  • Seasonal treats like hot chocolate, mulled cider, and festive snacks

  • Live music and holiday performances throughout the market

  • Historic, Dickens-inspired setting perfect for family fun and photos

Shop, sip, and savor the season while enjoying Annapolis’ cozy holiday charm!

📍 Location: St. John’s College, 60 College Ave, Annapolis, MD

 

Eastport Yacht Club Lights Parade – December 13 ⛵

Over 40 years of tradition sparkle on the water during the Eastport Yacht Club Lights Parade:

  • Festively decorated boats cruise Annapolis Harbor & Spa Creek

  • Prime viewing from Spa Creek Bridge, Eastport, or downtown waterfront streets

  • Free, community-centered holiday magic

Pro tip: catch the parade from a local boat cruise for the full coastal glow.

📍 Location: Annapolis Harbor & Spa Creek, Annapolis, MD

 

Snowflake Alley – Throughout December ❄️

Tucked into Cabbage Alley, Snowflake Alley is a twinkling pathway perfect for:

  • Romantic strolls along the waterfront

  • Holiday selfies and festive family photos

  • Exploring illuminated streets like Main Street, West Street, Maryland Avenue, and State Circle

Feel the charm of Annapolis’s historic downtown winter wonderland!

📍 Location: Cabbage Alley, Downtown Annapolis, MD

 

Lights on the Bay – Through January 1 🌟🚗

Cruise along the Chesapeake Bay for a two-mile drive-through light extravaganza, benefiting the SPCA of Anne Arundel County:

  • 70+ animated & stationary holiday displays

  • Pet-friendly walk-through nights, scavenger hunts, & Santa visits

  • Proceeds supporting local animal welfare

A perfect coastal holiday outing for families, friends, and festive road trips.

📍 Location: Sandy Point State Park, Anne Arundel County, MD

 

 Go Bowling Military Bowl – December 27 🏈

Wrap up the year with hometown pride and sports excitement:

  • ACC vs. AAC teams, live on ESPN

  • Free Tailgate Festival & pre-game pageantry

  • Military Bowl Parade on December 26, featuring marching bands and youth groups

Honoring service members while celebrating Maryland’s capital in true festive style.

📍 Location: Navy-Marine Corps Memorial Stadium in Annapolis, MD

 

✨ Why Visit Annapolis & Anne Arundel County This Holiday Season?

From glowing waterfronts and historic streets to festive parades and chocolate-filled fun, Annapolis offers a coastal holiday experience that’s as charming as it is magical. Whether you’re a local or planning a getaway, there’s something for every holiday traveler along the Chesapeake.