Lights on the Bay

Sandy Point State Park 1100 East College Parkway, Annapolis, MD, United States

See thousands of holiday lights and over  twinkle at Sandy Point State Park, where over 60 animated and stationary displays sparkle over the Chesapeake Bay. A holiday tradition, proceeds from Lights on the Bay benefit Anne Arundel Medical Center. Admission is $15 per car, $5o per bus. Open nightly November 18 - January 1, weather [...]

Grand Illumination, City Tree Lighting

Market House 25 Market Space, Annapolis, MD, United States

A Christmas tradition, the Annapolis Junior Chamber of Commerce will once again light up the Christmas tree at the city's Grand Illumination. Enjoy refreshments, help decorate the tree, shake hands with Santa Claus himself and bring nonperishable food items or new, unwrapped toys for the Chamber's Angel Tree Project. 

Jolly Express Cruise

Annapolis City Dock City Dock, Annapolis, MD, United States

Take a "sleigh ride"--except over the water except in the snow, and on a boat instead of an actual sleigh. The 45-minute holiday cruise includes seasonal music, hot chocolate and Santa steering the ship.  Happening weekends in December (excluding Dec. 10) including Christmas Eve, Christmas Day and New Year’s Eve 6:00 p.m., 7:00 p.m., and [...]

Chocolate Binge Festival

Downtown Annapolis Annapolis, MD, United States

Did somebody say chocolate? This third annual chocolate festival will feature holiday shopping, the lighting of the new West Street Light Canopy and lots and lots of chocolate. Located at the first block of West Street in Downtown Annapolis. Buy tickets here. 

Midnight Madness Holiday Shopping

Downtown Annapolis Annapolis, MD, United States

Come to the downtown "block party" and holiday shop 'til you drop! On the first three Thursdays of December, there will be live music and refreshments to enjoy while you stroll downtown and shop locally during the season of giving. Soak up the beauty of a lit-up Annapolis in the wintertime at this holiday event, [...]

Parade of Lights Cruise

Severn Inn 1993 Baltimore Annapolis Blvd, Annapolis, MD, United States

Eat dinner at the Severn Inn, then set sail aboard the Catherine Marie on a dessert cruise with unbeatable views of the Eastport Yacht Club Parade of Lights.  All-inclusive admission is $145.  Cruise begins and ends at the Severn Inn. 

Eastport Yacht Club Parade of Lights

Annapolis City Dock City Dock, Annapolis, MD, United States

Watch all kinds of decked-out boats parade through the Annapolis waterfront as thousands of lights twinkle and holiday music plays (usually from the boats!). Prime viewing areas include Eastport, Spa Creek, the City Dock and the Naval Academy sea wall. Admission is free. 

2017 Military Bowl

Navy-Marine Corps Memorial Stadium 550 Taylor Ave,, Annapolis, MD, United States

Watch representatives from the Atlantic Coast Conference and the American Athletic Conference face-off in the annual Military Bowl, benefiting the USO. 

New Year’s Eve celebration

Susan Campbell Park City Dock, Annapolis, MD, United States

Take part in family-friendly activities during the day then ring in the New Year with dancing and fireworks starting at 5:30 p.m. 

Blue Angels

Gather on the banks of the Severn River on the USNA campus to watch the amazing aerial performance of the Blue Angels.  Annapolis is very busy when the Blue Angles are flying, so be that parking may be limited. The following is a guide to watching these amazing sky acrobatics:  Tuesday, over the Severn River at 11:00 [...]

Go to Top