Ranked by Travel + Leisure as a 2023 Top Christmas Town!

The holiday season has arrived and our cozy coastal charm should be on your winter weekend bucket list!

Consistently ranked one of the best cities in America during the holidays, Annapolis is a great place to spend the winter holiday enjoying time with family and soaking in the holiday spirit.

A Chocolate Binge Festival, our Historic Tree Lighting, and the Lighted Boat Parade along the harbor are only a few things that set Annapolis & Anne Arundel County apart for the holidays. Explore more festivals and events and plan your winter escape on our website!

Chesapeake Bay Bridge Run

Do not miss your chance for one of the most thrilling and awe-inspiring road races in the country, the annual Chesapeake Bay Bridge Run!

This 10K race traverses the Bridge's eastbound span from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! These spots won't last long, register now!

Eastport Yacht Club Lights Parade

As America's Sailing Capital, it's only fitting that we showcase one of our favorite past times with a holiday parade unlike any other!  In 2022, the lighted boat parade ranked #6 out of 10 as one of the best holiday parades in the country by U.S.A. Today.

Visitors line up on the Annapolis waterfront and City Dock to watch the boats cruise by decked out with thousands of twinkling lights! Make this annual tradition a part of your family's holiday.

Annapolis Jazz & Roots Festival

Escape to Annapolis this fall for the Annapolis Jazz & Roots Festival for two weekends of culture, history, and, best of all - jazz and live music... Learn More

Annapolis Chocolate Binge Festival

The Annapolis Chocolate Binge Festival takes over the first block of West Street on Sunday, December 3, in a family-friendly celebration of all things cocoa... Learn More

Black Friday Shopping

Black Friday Deals- we are here for it and Arundel Mills has all the action! Shop Maryland's largest discount retailer for the best in fashion and holiday gifts for everyone on your list... Learn More

Midnight Madness

Don't miss Midnight Madness on Thursdays, December 7, 14, 21, where select stores in downtown Annapolis along Main Street, Maryland Avenue, and West Street will remain open until midnight giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night.

The stores pull out all the stops with over-the-top holiday displays, treats, special discounts, and sales for holiday shoppers. And, did we mention the llamas?

2023 Military Bowl

The 2023 Military Bowl will be played on Wednesday, December 27 at Navy-Marine Corps Memorial Stadium in Annapolis, Md. The National Capital Region’s college football bowl game once again will match teams from the Atlantic Coast Conference and the American Athletic Conference.

Last year, Duke defeated UCF, 30-13. The days leading up to the big game are full of activities including a historic pub crawl in downtown Annapolis, a meet and greet with the infamous Budweiser Clydesdales, and the Military Bowl Parade which traverses up Main Street ending at Navy-Marine Corps Memorial Stadium for an epic fan fest and tailgate prior to kick off!

Celebrate New Year's Eve in Annapolis & Anne Arundel County

This family-friendly event has been drawing tourists to the shores of Annapolis for years! The spectacle of the fireworks from the shore or on one of the many charter boats in the county makes for a festive and exciting way to ring in the new year.

With so many options and bespoke NYE celebrations happening across the region, you will find the perfect event to start 2024 off on the right foot.

Do you need more travel inspiration?
Follow us on social and stay connected!