Lifestyle

Whether you have in-laws visiting from out of town or you just want to get in the Christmas mood, Annapolis will be a hot-spot for huge holiday events starting now to the end of the year! Here are the top 15 can’t miss holiday events this year:

Lights on the Bay

Don’t miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit the SPCA of Anne Arundel County. Visit “Lights on the Bay” for more information.

When: November 23rd, 2019 to January 1st, 2020; 5:00 p.m. to 10:00 p.m. nightly, weather permitting
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: $15, car; $50, bus

Santa’s Cottage

Make the season extra merry with a visit to Santa’s Cottage this season. Capture the spirit of the holiday from November 23rd through December 24th as you enjoy a special meet-and-greet with Santa on different themed days, complete with a photo op, arts and crafts, and live snow! Themed nights include: Ugly Sweater Party, Pet Nights, Pajama Party, and even Milk & Cookies with Mrs. Clause!

The Towne Centre will also be partnering with Toys for Tots, the Anne Arundel County Police Department, and Kent Island High School to donate toys and a portion of sales from Santa’s Cottage will go to John Hopkins Children’s Hospital. Appointments to meet with Santa in advance are highly encouraged. Walk-in visits are welcome, though availability is limited. Make your appointment today.

When: November 23- December 24
Where: Annapolis Towne Centre

Jolly Express Cruise

Enjoy a 45-minute, holiday-inspired, “sleigh ride” cruise aboard the reindeer-bedecked Miss Anne. The cruise includes holiday music, hot cocoa, and Captain Santa at the helm. Visit www.cruisesonthebay.com for more information.

When: Fridays-Sundays, December 1st-31st, 2019; 6:00 p.m., 7:00 p.m., 8:00 p.m.
Where: Tours depart from the Information Booth at City Dock, Annapolis
Admission: $23, adults; $13, children under 12

Ugly Sweater Night

If you have ugly sweaters, whether ironic or gifts from grandma, that are collecting dust in your closet; get ready to break them out!  On December 4th and 11th from 6:00-8:00pm, select restaurants and bars at the Annapolis Towne Centre will be offering discounts on drinks to those sporting fun, goofy, and, most importantly, ugly sweaters! You can also hop over to Bin 201 for a special tasting, then to Santa’s Cottage for a photo op with the big man himself, and live snow for an extra touch of holiday spirit!

When: December 4th and 11th; 6:00 – 8:00 p.m.
Where: Annapolis Towne Centre
Admission: Free

holiday events

Midnight Madness Holiday Shopping

Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that is open to all. Enjoy musical performances as well as food and refreshments at many stores as you stroll along Main StreetState Circle/Maryland Avenue, and the Arts District in search of that perfect gift. Explore the uniqueness that makes downtown Annapolis so appealing at this magical time of year at Midnight Madness. Presented by the Downtown Annapolis Partnership.

When: Thursdays, December 5th and 12th, 2019; 6:00 p.m. to 12:00 p.m. December 19th, 2019; 6:00 p.m. to 11:00 p.m.
Where: Downtown Annapolis
Admission: Free

Holiday Candlelight Stroll

Learn about the origin of holiday traditions – including the significance of evergreens, Yule logs, Christmas trees and Santa Claus as you stroll through Annapolis with a festively attired guide. Includes a tour of the Hammond-Harwood House. Visit www.watermarkjourney.com for more information.

When: Fridays and Saturdays, December 6th-7th, 13th, 20th-21st, 2019; 7:00 p.m. to 8:30 p.m.
Where: Tours depart from the Information Booth at City Dock, Annapolis
Admission: $21, adults; $12, children ages 3-11; children 2 and under, free

State House by Candlelight

Enjoy this annual open house, State House by Candlelight, featuring performances by young musicians and vocalists from throughout Maryland. The oldest State House in continuous legislative use in the nation will be adorned with 24 Christmas trees representing every Maryland county and Baltimore City. Photo identification is required for individuals age 16 and older.

When: December 7th
Where: Maryland State House
Admission: Free

Fire & Ice

Take some time away from the busy holiday season for Annapolis Towne Centre’s Fire & Ice on December 7, 2019, from 4-8 pm. Embrace the winter with s’mores over a cozy fire, live music, a light show, on-site vendors, cocktails, shopping, and tasty bites.

When: December 7, 2019, from 4-8 pm
Where: Annapolis Towne Centre
Admission: Free

holiday events

Chocolate Binge Festival

If you like chocolate, you won’t want to miss this Chocolate Binge Festival, featuring chocolate and holiday vendors galore! Specialty restaurant candy events include a chocolate fountain, candy apples, candy floss, “chocolate sushi”, and more. Enjoy live music, a marshmallow roast, an ugly sweater contest, as well as a moon bounce and other kids’ activities. The evening wraps up with a grand lever pull to illuminate the sky above the first block of West Street. Presented by the Annapolis Arts District and Inner West Street Association. Visit www.annapolischocolatefestival.com for more information.

When: December 8th, Noon – 5 p.m.
Where: First block of West Street in downtown Annapolis
Admission: $5.00 cash donations are greatly appreciated!

Festive Friday

Ah yes, nothing to take you out of the holiday spirit like stressing about gift shopping. The Annapolis Towne Centre agreed and wants to change the game. This year, they are throwing Festive Friday on December 13th where participating stores will offer special discounts. And while you’re setting your bags down for a mid-spree break, you can enjoy special entertainment, enter for a chance to win some giveaways, and head over to Santa’s Cottage for pictures with Santa.

When: December 13th
Where: Annapolis Towne Centre
Admission: Free

37th Annual Eastport Yacht Club Lights Parade

The Annual Eastport Yacht Club Light Parade never disappoints with brightly decorated boats around the Annapolis waterfront as one of the City’s signature events. Thousands of lights and a host of jolly revelers make this a fun holiday event for the entire family. Prime viewing areas include:  Eastport, Spa Creek, City Dock, and Naval Academy sea wall. Sponsored by the Eastport Yacht Club. Visit the Eastport Lights Parade or Facebook for more information.

When: Saturday, December 14th, 2019; 6:00 p.m. to 8:00 p.m.
Where: Annapolis Harbor and Spa Creek
Admission: Free

Holiday Events

Lights Parade Dinner & Dessert Cruise

An Annapolis tradition. Enjoy dinner at Severn Inn followed by a dessert cruise aboard the luxurious Catherine Marie to watch the decorated boats cruising along Spa Creek in the Eastport Yacht Club Lights Parade. Visit their site for more information here.

When: Saturday, December 14th, 2019; 4:45 p.m. to 8:00 p.m.
Where: Begins and ends at the Severn Inn (1993 Baltimore Annapolis Blvd, Annapolis)
Admission: $152

City of Annapolis New Year’s Eve Celebration

Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year at this year’s City of Annapolis New Year’s Eve Celebration. For the second year, kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Participants are invited to park at Park Place garage and take City of Annapolis-provided shuttles to and from the new location. Activities will include face painting, an obstacle course, moon bounces and music performed by kids’ rock bands. The first round of festivities wraps up with on-site fireworks at approximately 5:30 p.m. Then, it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks.

When: Tuesday, December 31st, 2019, 3:00 p.m. to 5:15 p.m. kid-friendly activities; 8:00 p.m. to midnight for all
Where: Weems Whelan Fields behind Maryland Hall, 801 Chase Street, Annapolis and Susan Campbell Park, City Dock, Annapolis
Admission: Free

holiday events

New Year’s Eve Fireworks Cruise in Annapolis

Ring in the New Year on an exclusive and FUN fireworks cruise on Catherine Marie in Annapolis, Watermark’s flagship vessel. Includes and excellent – and comfortable – view of the city of Annapolis’ New Year’s Eve fireworks from the sparkling water. Enjoy dancing, DJ entertainment, celebrating and a full cash bar on board! Light snacks will be served. There will be hats and party noise makers, light bites and mini desserts, a great DJ with a festive countdown and a complimentary champagne toast at midnight! For adults 21 & over only. For more information, check out cruisesonthebay.com.

When: December 31st, 2019 10:00 pm to 1:00 am
Where: Tours depart from the Information Booth at City Dock, Annapolis
Admission: $90.00+

Lu Foster

Lu is a junior in college pursuing a Film Studies degree. In her free time, she enjoys writing scripts and books as well as making short films for fun. She lives locally but has worked in Annapolis for 3 years and involves herself with local events and festivals such as the Annapolis Film Festival.