Historic Annapolis Gingerbread Contest
December 1 -- January 1
Historic Annapolis Museum, 99 Main Street
www.annapolis.org

Nowhere in the world is there a greater repertoire of gingerbread recipes than in America. With the rich choice of ingredients, baking aids and decorative items the imaginative cook can create the most spectacular houses and centerpieces. Join Historic Annapolis as it hosts its annual gingerbread contest that provides a creative outlet for professionals and amatuers alike. Well-known Annapolis landmarks are recast in delectably spiced cake and confections. To participate, get your registration in by November 18. Prizes are awarded on December 10.

Jolly Express Holiday Lights Tour
Thursday through Sunday, December 1-31
Tours begin at 5 p.m., 6 p.m., 7 p.m. and 8 p.m.
City Dock, Annapolis
Admission: $21 for adults and $12 for children under 12
410-268-7601 x100
www.watermarkjourney.com

Hop aboard the Miss Anne for a Spa Creek Holiday Lights Tour aboard the Jolly Express. The 24-foot tug-style vessel is adorned with reindeer antlers and a blinking red nose on her bow. With Santa as its captain, the 45-minute tour takes in the lights around Annapolis Harbor and up Spa Creek.

Historic Annapolis Open House
Friday, December 2
6:00 p.m. -- 9:00 p.m.
www.annapolis.org

Kick off the holiday season with Historic Annapolis. All Historic Annapolis properties, including Historic Annapolis Museum at the St. Clair Wright Center, William Paca House and Garden, Shiplap House, Museum Store, Waterfront Warehouse, and 43 Pinkney Street, welcome visitors for the evening.

State House by Candlelight
Friday and Saturday, December 2-3
7:00 p.m. - 9:00 p.m.
Maryland State House, State Circle, Annapolis
410-974-3400

Enjoy choral, band, and ensemble performances by the glow of the official State Christmas tree in the oldest State House in continuous legislative use in the nation.

Holiday Candlelight Stroll
Fridays, December 2, 9 & 16 
Saturdays, December 3, 10 & 17
7:00 p.m. -- 8:00 p.m.
Tours depart from the Information Booth at City Dock, Annapolis
$16 adult / $10 children 3-11
410-268-7601
http://www.watermarkcruises.com/eventsTours.htm

Learn about the origin of holiday traditions from the significance of evergreens, yule logs and Christmas trees to the story of Santa Claus. This hour-long stroll guided by colonial-attired guide brings out the holiday spirit in everyone!

Historic Annapolis' Wreath-Making Workshop
Saturday, December 3
10:00 a.m. -- Noon
1 Martin Street, Annapolis
Admission: $50 general public / $45 HA members. Reservations required.
410-267-8146
www.annapolis.org

Add a handmade touch to your holiday decorations by creating a Colonial Revival wreath in this hands-on workshop, put on by Historic Annapolis. Expert floral arrangers will teach the fundamental techniques of making this classic evergreen wreath. Clipped boxwood, wreath forms and basic supplies are provided. You may also wish to personalize your wreath by bringing a variety of greens, fruit, seedpods, ribbons or other decorative materials to add.

Hanging of the Greens
Saturday, December 3
410-224-1775

Hanging of the Greens is an annual Annapolis Jaycees’ signature project. Local merchants contract with the Jaycees to decorate storefronts with holiday greens, lights, wreaths, and bows, transforming the Historic District into a beautiful holiday town.

65th Annual Handel's Messiah Concert with the ASO
Saturday and Sunday, December 3-4
8:00 p.m. Saturday and 3:00 p.m. Sunday
USNA Main Chapel
www.usna.edu/music
410-293-8497 (USNA Ticket Office)

Continuing a long-standing tradition, the USNA Glee Club joins the Annapolis Symphony Orchestra to present selections from Handel's beloved Messiah. Conducted by USNA Director of Choral Activities, this elegant concert has been broadcast on public television stations regionally and nationwide.

Children's Tree Trimming Party
Sunday, December 4
Captain Salem Avery House Museum, 1418 Shady Side Road, Shady Side, MD
1:00 -- 3:00 p.m.
Admission: Free
www.shadysidemuseum.org

Children of all ages are invited to a Tree Trimming party at the Captain Salem Avery House museum. Attendees will celebrate the holidays 1860s-style by taking part in an old-fashioned taffy pull and crafting Victorian gifts. Get into the spirit of the season by listening to stories and songs of holidays past. Rumor has it that Santa may stop by with candy for the young folk.

Home for the Holidays -- A WW2 Broadcast Concert
Sunday, December 4
7:00 p.m.
Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis
410-280-5640 (box office)
www.marylandhall.org

From the early 1930s through the 1960s, big bands were a powerful presence in the world of jazz and popular music. Names like Benny Goodman, Artie Shaw and Duke Ellington were the music stars of those days. The voices of Bing Crosby, The Andrew Sisters, and Nat King Cole brought listeners and dancers into their music with style and grace. Many of the now familiar holiday songs that we hear every year, like I'll Be Home For Christmas, White Christmas, and Have Yourself A Merry Little Christmas came from this era. The Brooks Tegler Big Band brings these classic songs to life with a show format based on the annual AFRS Transcription Nationwide radio shows that relayed "live" selections from nightclubs and theaters all around the nation.

Christmas with Aaron Neville and his Quintet
Monday, December 5
Rams Head OnStage, 33 West Street, Annapolis
8:00 p.m.
410-268-4545
www.ramsheadonstage.com

With warmth and sincerity, Neville lends his angelic voice to timeless holiday standards. Don't miss this performance as Neville succeeds in crafting a fun, Cajun-spiced yet traditional Christmas show, sure to capture all of the joy, passion, spirituality ,and nostalgia which goes along with the holiday season. This concert has become an Annapolis tradition.

Live Arts Maryland: A Celebration of Christmas
Thursday & Friday, December 8 & 9
7:30 p.m. Thursday / 8:00 p.m. Friday
Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis
410-280-5640
www.liveartsmaryland.org

This hometown Annapolis tradition is a must-hear for the holiday season. A holiday stocking full to the top with carols sung by a choir (of 160 voices!) and much much more. J. Ernest Green conducts the Annapolis Chorale, the Annapolis Chamber Orchestra, the Annapolis Youth Chorus and very special guests for this grand holiday event.

Concert: Peter White's Christmas
Thursday, December 8
6:30 p.m.
Rams Head OnStage, 33 West Street, Annapolis
410-268-4545
www.ramsheadonstage.com

There's an Englishman in the oversized red suit preparing to slide down the chimney of all the good little smooth jazz fans this holiday season. Peter White will deck the halls with jazzy versions of seasonal classics, a few original holiday songs and some of their best known hits. The show promises enough fun, funk, jazz and pop to get meanest of Scrooges into the spirit.

Midnight Madness Holiday Shopping
Thursdays, December 8 and 15
6:00 p.m. -- Midnight
Downtown Annapolis

Lights, garland, action! Historic Annapolis’s 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 Street, Maryland Avenue, inner West Street, and State Circle in search of that perfect gift. Explore the uniqueness that makes downtown Annapolis special. Sponsored by Annapolis Business Association.

Home for the Holidays eCruiser Tour
Nightly until January 1
5:30pm - 11:00pm
Downtown Annapolis
Admission: $25/adult, first child free
443-510-1348

See Annapolis at Christmas like you’ve never seen it before. Join Annapolis Urban Adventures for its inaugural "Homes for the Holidays" excursion. These 1-hour tours take in the "lights & sights" as you relax and ride through town on the all-electric eCruiser. Make your reservation now.

Ballet Theatre of Maryland: The Nutcracker
Saturdays and Sundays, December 10 & 11 and December 17 & 18
7:00 p.m. Saturday / 1:00 p.m. and 4:30 p.m. Sunday
Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis
Admission: $45 Adult / $19 Children 10 and under
410-280-5640
www.balletmaryland.org

The possibility of dreams comes true when you relive Clara's adventures as she helps her beloved Nutcracker defeat the evil Rat Queen and enters the land of dreams in this holiday classic. A cash bar lounge is available on Saturday night performances one hour prior to the performance and during intermission. Patrons of the Sunday performances are invited to meet Clara and the Nutcracker Prince at the ever popular Sugar Plum parties that take place prior to each performance. Children can have their picture taken with their favorite Nutcracker character or with Santa Claus. Sample special sugar plum treats and other fare and share in the tradition!

Eastport Yacht Club Lights Parade
Saturday, December 10
6:00—8:00 p.m.
Annapolis Harbor and Spa Creek
410-267-9549
www.eastportyc.org

Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold wintry night illuminated with thousands of colored lights and crewed by jolly revelers. Families and friends gather at their favorite viewing spots along the waterfront to see this yearly spectacle and to celebrate the holiday season together. The Eastport Yacht Club Lights Parade is one of Annapolis’ signature holiday events.

An Annapolis Christmas
Monday & Tuesday, December 12 & 13
7:00 p.m.
Rams Head OnStage, 33 West Street, Annapolis
410-268-4545
www.ramsheadonstage.com

Join your favorite local artists as they perform a mix of original and classic holiday songs, all on one stage. This show was inspired by the release of the popular holiday album, "An Annapolis Christmas" over ten years ago, and is now an annual tradition for many local music lovers. All proceeds from this show support the Annapolis Musicians Fund for Musicians.

Annapolis Chorale Chamber Chorus Concert
Thursday, December 15
6:00 p.m. to 7:00 p.m.
St. Anne’s Episcopal Church, Church Circle, Annapolis
Admission: Free
410-263-5989
www.liveartsmaryland.org

Come enjoy the sounds of the season during a free, hour-long concert with Annapolis Chorale Chamber Chorus performing "Carols for the Season." Let your busy day end on a musical note or start a fun evening with the soaring harmonies of one of the largest and most active performing ensembles in the region.

Annapolis Symphony Orchestra's Holiday Pops
Friday, December 16
8:00 p.m.
Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis
Tickets: from $25 / Students $10
410-263-0907 (box office)
www.annapolissymphony.org

Simply Sinatra Christmas is a terrific new holiday show featuring Pops sensation Steve Lippia and the ASO. Steve presents popular holiday songs along with some of the most beloved numbers performed by Frank Sinatra. This show is a wonderful blend of holiday cheer and swing standards with an energetic flair that only a big band can provide. You will be treated to many great, long-time holiday favorites like “White Christmas,” along with standards such as “All The Way” and “Summer Wind.”

Live Arts Maryland:  Messiah -  G.F. Handel
Friday, December 16 and Sunday, December 18
8:00 p.m. Friday / 3:00 p.m. Sunday
St. Anne's Church, Church Circle, Annapolis
410-280-5640
www.liveartsmaryland.org

In the acoustic and historic splendor of St. Anne’s Church, in the soft glow of candlelight, Handel’s masterpiece comes to majestic life again as performed by the Annapolis Chorale Chamber Chorus, Annapolis Chamber Orchestra and a quartet of world-class quartet of soloists, including soprano Brandi Sutton, whose soaring “Rejoice Greatly” dazzled audiences last season, and baritone Shouvik Mondle, who majestically duets with the orchestra brass on “The Trumpet Shall Sound.” 

"It's A Wonderful Life" in West Annapolis
Saturday, December 17
10am-8pm
410-295-5157
www.westannapolisbusiness.org

Enjoy a nostalgic holiday event with Santa, shopping, children's activities and entertainment. Free horse and carriage rides from 5pm-8pm. Watch a holiday classic--It's A Wonderful Life--showing throughout the day. A portion of merchant sales will be donated to local charities.

Live Arts Maryland:  A Celebration of the Nativity
Saturday, December 17
8:00 p.m.
St. Anne's Church, Church Circle, Annapolis
410-280-5640
www.liveartsmaryland.org

The second night of the Live Arts Maryland Messiah weekend is a candlelight concert with segments of Messiah’s Part I and a set of moving carols that recall and honor the divine events in Bethlehem.

Season of the Sailor
Sunday, December 18
7:30 p.m. to 9:30 p.m.
Annapolis Maritime Museum, 723 Second Street, Annapolis
Admission: $15 in advance and $20 at the door
410-295-0104
www.amaritime.org

Annapolis duo Calico Jack joins forces with Virginia native and traveling troubadour Bob Zentz for an evening of original and traditional seasonal songs from the maritime tradition. Sit back with a cup of eggnog and sing along with songs sailors sang during the long winter months at sea, songs they wrote about spending the holidays afloat, and songs and stories they enjoyed on their rare times at home during the holidays. Calico Jack will offer the Chesapeake Bay in winter: dredging, root beer, and the annual fireman’s feast, and Zentz will dig into his compendium of sea lore from the Bay and beyond.

Annapolis New Year's Eve
Saturday, December 31
3pm - midnight
Downtown Annapolis

Every New Year's Eve, downtown Annapolis features entertainment and spectacular fireworks for the entire family. For the young and young at heart, plan to be at Susan Campbell Park, City Dock, from 3:00-7:30pm. Annapolis Children's Museum returns with their Children's Fun Time starting the day at 3pm....and be sure to stick around for the 7:30pm fireworks.  "Dancing Under the Stars" with the Big Band Sound begins at 8pm and takes you to the midnight countdown as we greet the New Year with midnight fireworks!