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. 

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. 

Father’s Day Brunch Sail

Annapolis Sailing Cruises Schooner Woodwind 80 Compromise St., Annapolis, MD, United States

Treat your father to brunch on a boat this year! This sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $92 per person, $52 per [...]

$92

Halloween on the Avenue Festival

Maryland Avenue & State Circle Merchants Association 69 Maryland Ave, Annapolis, MD, United States

Annapolis Bootique District hosts their fun fall festival, Halloween on the Avenue Sunday, Oct. 21st 10am-5pm on Maryland Avenue and State Circle. This family-friendly event includes musical entertainment, a doggie parade, great shopping, and of course, tricks and treats! 

Hammond-Harwood House Pumpkin Walk

Hammond-Harwood House 19 Maryland Ave., Annapolis, MD, United States

$15 per family/$10 Member’s family For reservations, please call 410-263-4683×10 or email info@hammondharwoodhouse.org Buy Tickets Join us for our annual Pumpkin Walk!!! The event will celebrate the season with games and a costume parade around the mansion. Kids will enjoy several fun activities and will learn about the architecture of the house. Witch telling stories, face painting, pumpkin [...]

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