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1. Annapolis by Candlelight November 8 and 9 , 5pm, Murray Hill
2. Grand Illumination Tree Lighting December 1st, 5:30-7pm, Market Space
3. Chocolate Binge Festival December 8, 12-5pm, West Street
4. Midnight Madness Holiday Shopping December 5, 12, and 18th, Downtown Annapolis
5. Eastport Yacht Club Lights Parade December 14, 6-8pm Annapolis Harbor and Spa Creek
6. Military Bowl December 27th 12pm, Navy- Marine Corps Memorial Stadium

“A crisp autumn evening is the perfect time to walk through one of the historic neighborhoods of Annapolis. The experience is even better when the doors to some of the homes are open and you are invited inside. Each year, Historic Annapolis showcases privately-owned historic houses on its popular Annapolis by Candlelight tour. Visitors see how 21st-century Annapolitans care for and live in historic buildings. Each house is a reminder of the rich architectural and cultural heritage of Maryland’s capital city and illustrates the practical and aesthetic benefits of effective historic preservation. This year’s tour will feature homes in the Murray Hill neighborhood.”

– Facebook Annapolis by Candlelight

“A Christmas tradition, the Annapolis Juinor 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”

– Annapolis.com

“Chocolate lovers come together to enjoy a day to celebrate the art of chocolate. There is something for everyone including over 35
Chocolate vendors, shopping from dozens of local artists, drinks, food, and live music and did we mention Chocolate.Plus we will have our popular Smores Firepit, Cocoa with the PoPo, Holiday Market, a free Hot chocolate (while supplies last) with paid admission. Live music throughout the day. The music schedule will be posted here soon.”

– Facebook Chocolate Binge Festival

“Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that’s open to all. Enjoy outside musical performances as well as food and refreshments at many stores as you stroll along Main Street, Maryland Avenue, West Street, State Circle and City Dock in search of that perfect gift. Sponsored by the Downtown Annapolis Partnership.”

– Patch.com  

“More than 30 brightly lit boats bedecked for the holiday season parade around the Annapolis waterfront and Spa Creek. Themes including Santa Claus, Polar Bear Christmas, Crabby Chesapeake Christmas, a Christmas Angel and the Abominable Snowman have delighted young and old. Thousands of lights and a host of jolly revelers make this a fun Christmas event for the entire family. Prime viewing areas include Eastport, Spa Creek, City Dock and the Naval Academy seawall.”

– Visitannapolis.org

” The AAC will face off against the ACC in the 2019 Military Bowl presented by Northrop Grumman Corporation. For the 10th consecutive bowl season, the Military Bowl will be benefiting the USO and will provide at least $100,000 to the USO. Complimentary tickets to troops and their families will also be distributed for the game through the USO of Metropolitan Washington- Baltimore in early December.”

– Visitannapolis.org