You know the holidays are fast-approaching when every category below offers some holiday-themed event. From the Lights Parade to the holiday version of Green Drinks, Annapolis seamlessly weaves together seasonal cheer with entertainment.

Annapolis Entertainment

Most notably, this week welcomes the Eastport Yacht Club’s Parade of Lights. This much-anticipated event is free, reminiscent of old Annapolis traditions, pet and child-friendly, and fun. Boats decorated with Christmas lights and colors will circle the Harbor for spectators to see. The show is scheduled for Saturday, December 14, from 6 p.m. to 8 p.m. View EYC’s website for additional info.

Just as valuable to the community as the Lights Parade is downtown’s Midnight Madness, put on by Annapolis Business Association with help from sponsors. The second round of this three-part shopping experience comes this week on Thursday, December 12. Downtown businesses will be open until midnight to welcome shoppers. Discounts and goodies may be offered at your favorite stores. There is no pass needed, just park and shop!

West Annapolis celebrates their own type of spirited holiday, with the annual “It’s a Wonderful Life Celebration.” Inspired by the joyous cheer in the movie, West Annapolis businesses will provide incentives and special holiday items for shoppers. Santa will be in attendance, as well as volunteers who offer free horse and carriage rides from 5 to 8 p.m. The celebration lasts from 10 a.m. to 8 p.m. Head to West Annapolis Business Affiliation to learn more.

End-of-the-year holidays combine community feelings and joy that’s often said through actions, not words. The USNA Band attempts to speak through music at one of their first holiday shows of the winter season, scheduled for Wednesday, December 11. This group of musicians performs at the Naval Academy Main Chapel for free from 7:30 to 9 p.m. on this date. Holiday tunes will be performed.

On December 14, the classic rivalry of Navy versus Army in football will commence at 3 p.m. The Naval Academy Band will be there along with tons of fans rooting for the home team. More information about these Navy events can be found at USNA’s site.

The fabulous and fluid Nutcracker, as performed by Ballet Theatre of Maryland, continues this Thursday, Saturday, and Sunday. Much revered for talented dancers and exquisite plot lines, the Ballet Theatre of Maryland’ Nutcracker performance is one that shouldn’t be missed. The show is held at the Maryland Hall for the Creative Arts. For ticket information, please visit Ballet Theatre of Maryland’s site.

Two other holiday music performances are scheduled for this weekend. The first, on Friday, is entitled “Celebration of Christmas,” and welcomes Grammy-nominated singers to sing an ode to Christmas tunes we all know and love. Enjoy the carols and sing along if you’re so inclined with this show held at Maryland Hall. This performance begins at 8 p.m. and costs $48. Next, Saturday brings “Carols by Candlelight,” a smaller, more intimate music performance. The Annapolis Chamber Orchestra performs along with other seasoned vocalists. St. Anne’s Church hosts this show that starts at 8 p.m. Tickets start at $15. For more on these events, activate the link to Maryland Hall’s site.

The most jolly cruise you’ll ever take–the “Jolly Express Cruise” from Watermark–also continues this week. The cruise circles Spa Creek and area waters. This week, cruises run December 13 and 15. The price is only $22 for adults and $12 for kids. To book this cruise or the ones described below, head to Watermark Cruises.

Recurring events certainly afford flexibility in scheduling, but those once-a-year events are the ones to get most excited about. This week, “The Queen of all Food Drives” cruise, offered by Watermark, comes in conjunction with the annual Eastport Yacht Club Lights Parade, as described at the top. The cruise gets its name from the admission, which is simply a donation (non-perishables, cash, etc.) to Anne Arundel County Food Bank. Watch the lights show aboard the Harbor Queen, docked at City Dock. Board the boat around 5:30. Pets are welcome too! Go to the above link to learn more.

Annapolis Green

Green isn’t just a quintessential Christmas color, it’s a mindset adopted by many here in Annapolis (excuse the holiday pun). Tuesday, December 10, a holiday version of Green Drinks is scheduled at the Metropolitan Kitchen & Lounge on West Street from 5:30 to 7:30 p.m. This green social networking event is free and open to all. To learn more about it, head to Annapolis Green, your resource for all things green.

Annapolis History

Learn to make something unusual yet welcomed as a gift for the holiday season. The Historic Annapolis Museum Store on Main Street is offering a “Beaded Embroidery Holiday Ornament” workshop this Saturday, December 14. The price is $25 for the general public and is offered from 10 a.m. to noon. Head to Annapolis Historic Foundation for more info.