View historic, nighttime Annapolis by candlelight while taking a walking tour of private homes which, this year, will focus on historic neighborhoods in the vicinity of Prince George and King George Streets.
Bizarre as it sounds, lots of money is raised for Annapolis charities every year at the longest tug-o'-war over a body of water in the world. Annapolitans face off against the fictional Maritime Republic of Eastport while 100+ spectators join in on the fun in the festival-like atmosphere downtown. Tug of War XX will begin [...]
As always, enjoy live entertainment and the work of over 100 artists outside in the city's Arts District--this time with a holiday twist! Find gifts for family and friends or pick up a souvenir for yourself that's 100% original. Festival can be found next to the Whitmore parking garage on West Street and Calvert.
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 [...]
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.
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 [...]
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.
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, [...]
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.
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.
