annapolis yacht club christmas party

Eastport Yacht Club Lights Parade

December 14, 2024, from 6 - 8 p.m, the eastport yacht club's lights parade to celebrate its 42nd year in 2024.

The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for 40 years!

It all began in the 1980s when  Eastport Yacht Club  (EYC) started. Back then, the club was based in a fourth-floor room with a tiny bar in a complex in what is now  Annapolis City Marina . Some of the earliest members lived on boats in that marina and used the club as their living room, especially after the weather got cooler. Feeling the spirit (pun intended) one December night, a few took to their boats and tooled around the harbor, singing Christmas carols.  1

Because it was so much fun, the EYC members decided to build upon the parade by adding lights to decorate their boats, making it an annual tradition. Although several tour operators sell packages during the lights parade, where you can watch the event on the water, the event is free. (Click here for more tours.) Now, it is an officially sanctioned and sponsored event on the Annapolis & Anne Arundel County holiday calendar.

Where to Watch

Book a cruise, join a friend's boat or watch from the Annapolis city front or Spa Creek Bridge. More great viewing spots are at the end of any street in downtown Annapolis that ends at the water. Pocket parks in Eastport and Murray Hill are also great vantage points for sipping some cocoa and watching the boat parade sail by.

To learn more about the parade's history, read this great blog on Annapolis Discovered .

1  Quote taken from the blog:  Behind the Mask: Tom Stalder & the History of the EYC Lights Parade

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Insider's Guide: Eastport Yacht Club Lights Parade

December 5, 2023

Ryan Sneddon

Like many things in Annapolis, our best holiday tradition involves the water. It’s the Eastport Yacht Club Lights Parade and here’s exactly what you need to know to enjoy it.

First Things First: The Basics

The 2023 Eastport Yacht Club Lights Parade is December 9 from 6–8 PM. All of the action either happens in the harbor or down Spa Creek & Ego Alley.

Where can I watch?

Any of the pins on the map above are good options. Most of the street end parks are quite small so stake out your spot early.

Best viewing points

Spa creek bridge.

This is the best vantage point but fully exposed to the wind so it can be mighty cold. But you can see both fleets and get a close up when they switch places.

This is as close as you can get to the boats without being on one. Get here early if you want to see every little detail of how the displays are constructed.

Get a great view of all the boats as they circle around the harbor. You can get a higher vantage point if you join the We Care and Friends fundraiser on Watermark’s Harbor Queen. In lieu of tickets, bring a monetary donation, toy, blanket, clothing, or non-perishable food item to get in.

Other viewing options

If you have friends with homes or offices on the water, time to get them an early Christmas present and hope for an invite.

The Choptank is also a great option but space is limited and last year there was a private party on the entire second floor.

Where do I park?

The official parking garage of the parade is the garage at Park Place – 100 Westgate Circle, Annapolis, MD 21401 . The free circulator shuttle will run downtown.

Other options include:

• Hillman Garage . Cost: not free. Likelihood of spot: low
• Gotts Court Garage . Cost: not free. Likelihood of spot: medium
• Calvert Street Garage . Cost: free on weekends. Likelihood of spot: high
• Knighton Garage . Cost: not free. Likelihood of spot: medium
• Street parking . Cost: not free. Likelihood of spot: low

Remember that you get 1 hour free in the Hillman Garage and two hours in meter spots by using the code ParkDTA on the ParkMobile app until New Year’s Day.

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Annapolis Christmas Lights Boat Parade

Everything You Need to Know About the Eastport Yacht Club's Parade of Lights

Eastport Yacht Club Parade of Lights

Maryland's capital city celebrates Christmas in style with the Eastport Yacht Club Parade of Lights , a 30-years-and-running holiday tradition in which boat owners flaunt their best light decorations in an Annapolis Harbor procession. This is one of the most popular events of the season and a quirky, sometimes comical way to celebrate with family and friends. The event takes place every year on the second Saturday of December, but in 2020, it's been canceled. Still, many boats in the harbor will carry on the tradition of decorating their decks.

Where to Watch the Parade of Lights

The boats parade along the Annapolis Harbor and Spa Creek Waterfront, extending from Primrose Road to the south and the USNA Seawall to the north. Be sure to arrive early to stake out a good viewing spot (and dress warmly—temperatures are likely to be in the 40s at best).

WNAV Radio 1430 provides live coverage of the parade via roving reporters from 6 to 8 p.m. It announces the winners of the decorating contest at 10 p.m. They're also announced over marine radio Channel 72. A live feed is broadcast during the parade at the  Annapolis Smokehouse . Many other downtown bars and restaurants offer specials to entice visitors to stay after watching the Parade of Lights at one of these locations.

• Eastport Bridge
• Fawcett Boat Supplies Parking Lot at 110 Compromise Street
• Naval Academy
• Annapolis City Dock
• The walkway in front of Annapolis City Marina in Eastport
• Aboard the  Catherine Marie , which usually serves dessert and champagne during the parade
• Aboard the Harbor Queen , moored at the end of the City Dock and usually conducting a food drive during the parade
• Other spots include Market, Shipwright & Revel Streets, Acton Cove, Southgate, Taney and Cheston Avenues, Lafayette Park, Monticello Avenue, Truxton Park, Burnside Street, Fourth Street, Third Street, Second Street, and First Street. 

David Clow / Flickr CC 2.0 

Transportation and Parking

Parking is restricted and limited in many places near the Annapolis Harbor. The main parking site for the parade is usually the garage at Park Place, 100 Westgate Circle (across from the Annapolis National Cemetery). Signs on Rowe Boulevard and Taylor Avenue will direct visitors, then a free city shuttle will take them from Park Place to downtown every 10 minutes, running until 2:30 a.m. Additional garages are available, including Knighton Garage (Colonial Avenue), Gott's Court Garage (25 Northwest Street), South Street Lot (South Street off of Church Circle), and Hillman Garage (150 Gorman Street).

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Eastport Yacht Club Lights Parade

The eastport yacht club lights parade is a magnificent event that happens the second saturday night in december each year.  a fleet of boats adorn lights in many different and creative ways.  the cost of tickets for last year was $85.00 per person.  this includes a three course dinner, gratuity, access to our deck for prime viewing, and parking.  we sell tables like season tickets for a sporting event.  guest from the previous year will have the first right to purchase their table for the current year.  tables of 4 are the most common to come available. although reservations are difficult to obtain during the event, we will be seating our dining room after the show on a first come basis.  tables will usually become available after 8:30.  if you would like to dine with us after the show, please check in with the host/hostess upon arrival to the restaurant.  we recommend viewing the show from many of the public areas within our complex.  our inside bar will be open to the public along with an outside bar that evening.  unfortunately, parking that evening is limited to guests with reservations in the restaurant.  street parking is possible but limited.  if you would like to put your name on our waiting list for reservations during the show, please use the form below.  the waiting list for the 2024 show will start at 12 am december 9, 2023.   , lights parade wait list.

December 15, 2023

Annapolis Holiday Tradition Shines Bright with Eastport Yacht Club’s Christmas Lights Parade

Club News , Featured News , Station News ,

In what has become a signature event of the Annapolis Holiday Season, the Eastport Yacht Club's Christmas Lights Parade illuminated the waters with a spectacular display of festively adorned boats. This annual extravaganza, a testament to community spirit, featured 51 boats bedecked in holiday lights and decorations.

The tradition began with a couple residing on a boat docked in Spa Creek, at the heart of Annapolis on the Eastport side. Transforming their boat into a festive spectacle, they invited friends for a harbor cruise complete with Christmas carols. As the years passed, more boats joined the festive procession, leading to the formation of the Eastport Yacht Club. Over time, the event evolved into an official club function, complete with a spirited competition among members for the most creatively decorated boat.

The City of Annapolis embraced the Christmas Lights Parade, making it an integral part of the holiday festivities. The event has since grown in scale and popularity, attracting participants and spectators alike.

Notably, the driving force behind the Christmas Lights Parade is a couple who has dedicated over 25 years to its organization – Tom and Trudy Stalder, now proud members of the Storm Trysail Club (STC). Their commitment extends beyond the parade itself, involving year-round efforts in securing sponsors, collaborating with charities, and coordinating with various government agencies, including the Department of Natural Resources and the Coast Guard.

The logistical challenges are numerous, from ensuring the safety of participants to coordinating the opening of the drawbridge across Spa Creek for prime viewing. Steering boats with limited visibility amidst a sea of twinkling lights presents its own set of challenges, making the effort a year-round labor of love for the Stalders.

Jeff Goldring, Chesapeake Station Captain of the Storm Trysail Club, expressed great pride and pleasure in welcoming Tom and Trudy Stalder as members of STC. The connection between the sailing community and the Christmas Lights Parade highlights the vibrant and diverse interests of its members.

As a poignant footnote, Goldring shared a personal connection to boat parades, revealing that his wife Carol's father, Fran Schuster, played a pivotal role in initiating the boat parade in Ft. Lauderdale in 1965. Much like the Annapolis tradition, the Ft. Lauderdale Boat Parade has evolved into a massive spectacle featuring predominantly commercially sponsored and professionally decorated yachts, reflecting the enduring appeal of these luminous celebrations on the water.

More pictures: https://www.eastportyc.org/lights-parade

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40 years and counting for the Eastport Yacht Club Lights Parade in Annapolis Harbor

This year the parade will take place from 6 to 8 p.m. on Dec. 10 , when boats decked out in holiday lights will be paraded up Spa Creek and through Ego Alley.

The Light Parade started as a one-man show in the early 1980s when Jim Langer, while living on his boat in Spa Creek, adorned it with Christmas lights and paraded around Annapolis Harbor. It caught on over the years, turning into a multi-boat extravaganza over the next four decades. By 1988, the event was proclaimed the official Maryland Winter Celebration.

Annapolis invites everyone to find a good spot along the parade route to see colorfully lit boats on a crisp December evening.

“Make sure you come out early because in the past it’s been pretty busy,” said Trudy Stalder, an Eastport Yacht Club member who hasco-chaired the Light Parade for the last four years with husband Tom Stalder.

Spectators can see the parade from several places, from the Eastport Bridge to finding a spot at the Eastport Yacht Club. There will also be vantage points along City Dock, Susan Campbell Park, the Naval Academy sea wall and other spots along Spa Creek.

During the event, Watermark is teaming up with We Care and Friends to host a dockside fundraiser from 5:30 to 9 p.m. aboard the Harbor Queen. There will music, drinks and a front-row seat to the parade. In lieu of a ticket, We Care and Friends, a nonprofit organization based in Annapolis that helps people struggling with substance abuse, will be collecting monetary donations as well as toys, linens, bedding, blankets, toiletries, clothing, and non-perishable food items.

Watermark has partnered with different organizations like this since 2011 and are excited to uphold the tradition to help a worthy cause.

“It is an absolute pleasure to partner with We Care and Friends for this year’s Queen of All Fund Drives. They do phenomenal work to help our community,” said Jake Iversen, president of Watermark, in a statement. “The Lights Parade is an Annapolis tradition, and we hope to see a big turnout to enjoy the festivities and support this wonderful organization.”

This year, there will be more than 40 boats participating in the parade, a number Tom Stalder said he hopes will continue to increase as the event gets closer.

“This show was up to 65 boats in the late ’80s,” he said. “It’s been down into the 30s recently but last year we were up to 40 before we canceled and this year we have more than that and counting. Hopefully, the trend continues.”

Stalder said he believes LED lights have allowed more boaters to light their crafts for a more reasonable price. He recalls when boaters needed a generator to keep their boat lit up.

“We expect to see all kinds of creative lighting ideas some by theme and others with moving lights spelling out fun holiday messages,” Stalder said.

Stalder said they are seeing new registrations every day, adding that participants don’t need to be part of the Eastport Yacht Club.

The Stalders said they take great pride in being able to help present the parade to the city each year because it starts the holiday season in Annapolis.

“It’s like our gift to the city,” Trudy Stalder said.

The event will coincide with other holiday events happening in the city. The Annapolis Holiday Market will be open from Dec. 8 to 11 at City Dock, along with Midnight Madness, when downtown businesses stay open late on Dec. 1, 8 and 15, leading up to Christmas..

The city of Annapolis asks those planning to watch the parade to be mindful of the potential for cold air and water temperatures along with slippery surfaces on boat decks and near the water’s edge.

The rain date for the event is Dec. 9.

Check the Eastport Yacht Club’s website for registration and inclement weather information. Deadline to register a boat in the parade is Dec. 6.

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Lights Parade Dinner Cruise with Ken's Creative Kitchen

Dates available.

Saturday, December 14th

Upcoming Dates

Sat 5:00 pm - 8:00 pm

Description

Join Watermark and Ken’s Creative Kitchen aboard Raven for an intimate holiday dinner. Live jazz and holiday classics with Fred Hughes and Steve Meashey will set the mood for appetizers and dinner on the main deck. Then, venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade. Included in the ticket are an open beer and wine bar, butler-served hors d'oeuvres, as well as dinner and dessert service at a private table. Seating is limited, and reservations are for tables of two, four, or six; Larger parties may select multiple tables (or call us for odd numbers); Please specify if you will be joining another party and your entrée selections in the reservation notes.

Learn more about Fred Hughes !

Butler-Served Hors d’Oeuvres

Sautéed Jumbo Lump Maryland Crab Cakes, Lemon-Dijon Aioli

Chilled Jumbo Gulf Shrimp, Tomato-Horseradish Sauce

Shaved Virginia Smithfield Ham, Buttermilk Biscuits and Red Pepper Jelly

Dinner Service: First Course

Harvest Autumn Salad – Burgundy Lettuces, Little Gem Lettuce and Watercress, Dried Cranberries, Spiced Candied Pecans, Wedge of Roquefort, Roasted Butternut Squash, Blossoms, Vermont Maple Vinaigrette Dressing

Dinner Service: Entrée Served

Roasted Fillet of Chesapeake Bay Rockfish – Jumbo Lump Maryland Crabmeat, Savory Lemon Soufflé, Warm Bundle of Asparagus with Leek Ribbon, Dauphinoise Potato Medallion

Sea Salt and Cracked Black Pepper Roasted Tenderloin of Beef, Medium Rare – Shallot-Wild Mushroom Pinot Noir Sauce, Deep Fried Shoestring Sweet Potato Garnish, Dauphinoise Potato Medallion, Warm Bundle of Asparagus with Leek Ribbon

Sage and Parmesan Polenta Triangles – (Vegetarian, Gluten Free, Nut Free) – Oven Roasted Eggplant, Zucchini, Yellow Squash, Sweet Red Pepper, Vidalia Onions and Portobello Mushrooms, Cherry Tomato Marinara, Fresh Basil Garnish, Fresh Thyme

Warm Pear in Puff Pastry – Bourbon-Cinnamon Ice Cream, Port Wine Reduction Sauce, Sweet Cream, Fresh Mint

Departure Location

Annapolis City Dock 1 Dock Street, Annapolis, MD, 21401

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HOAGonSight

Photo Stories by Hoag Levins

The View From The Annapolis Christmas Boat Lights Parade

New Orleans has its Mardi Gras; Philadelphia, its Mummer’s Parade; New York, its Macy’s celebration of giant balloons. Here in this Chesapeake Bay city of famed as the country’s sailing capital, they have the Annapolis Christmas Boat Lights Parade. Actually, that’s not its real name: The Eastport Yacht Club Lights Parade. And this year’s parade was as popular as the last 36 have been. As darkness descended across the water, a cannon went off and captains in three dozen boats switched on the wildly festive lights that festooned their vessels. Among the first to show at the bridge that serves as the parade’s entrance point were five sailboats rigged with mast-high Christmas trees of lights. They resembled a small stand of holiday evergreens moving in line across the water.

25 Best Annapolis Events To Celebrate Christmas In Maryland

Annapolis is a waterfront town bathed in history, with a very walkable historic district and suburbs that meander outwards, providing even more opportunities for winter adventures. As the capitol of Maryland, Annapolis Events embrace the history of Christmas in Maryland, as well as some newer traditions.

Any seasonal festivities tend to be permeated with a strong sense of community pride in Maryland’s rich history and seaside economy. So don’t be surprised by some blue crab memorabilia or a few colonial ghosts popping up wherever you go. Whether you like exciting outdoor light shows or cozy musical venues, Christmas in Annapolis will have the event to start your holidays off right.

Remember, events are always subject to change. It is always a good idea to check the website and call ahead to confirm timing and any special precautions that are in place.

Winter Blooms in Historic London Town

• Address : Historic London Town and Gardens, 839 Londontown Rd., Edgewater, MD
• Dates :  November through mid-December, re-opens in mid-January. (Check website for updated dates/times.)

Enjoy the stunning views of South River on a walk through 10 acres of woodland and ornamental gardens. This flower-centric arboretum places its hardiest winter blossoms, like the bold white, pink and red Camellias, front and center for a burst of color all year long.

Other winter favorites include fragrant evergreens, beautiful holly and delicate viburnum. The grounds also give visitors a taste of history with reconstructed colonial buildings, including the Lord Mayor’s Tenement, the Carpenter Shop and the National Historic Landmark William Brown House.

This is a popular site for school trips, with exhibits that are kid-friendly and staff who are happy to answer questions from students (and their parents).

Get a New View of the City with Holiday Cruises

• Address : Departs from City Dock, Annapolis, MD .
• Dates: Cruises run daily throughout November & December; special holiday packages on weekends in December. (Check website for updated dates/times.)

A cruise along Spa Creek past downtown Annapolis is a must for visitors any time of year. But that’s especially true during the holidays, when special tours provide an extra dose of Christmas fun.

Families should check out the Jolly Cruise Express or Captain Santa’s Cruise, both of which feature caroling, sweet treats and the Big Man himself at the helm! (Where does Santa find the time?)

For those who like some variety in their holiday events, try the Holiday Stroll & Cruise, which starts with a historic tour of Annapolis with a guide in period costume, explaining the colonial traditions of the holiday season. Then visitors board the decked-out Saint Anne for a relaxing 40-minute cruise.

Or check out a Holiday Dinner Cruise with Ken’s Creative Kitchen, featuring beer and wine, and dinner on an enclosed deck and live jazz. Then head to the open-air top deck, enjoying the view of Eastport Yacht Club’s Lights Parade.

Of course, the standard boat rides of Annapolis are just as fun during the holidays as any time of year. For our money, the best bets are the romantic Harbor Lights evening cruise aboard the Harbor Queen, or the “Spirits & Spirits” haunted walk and booze cruise for some ghostly Dickensian fun.

Lights on the Bay for Animal Welfare

• Address : Sandy Point State Park, 1100 East College Parkway, Annapolis , MD
• Dates: Nov.-Jan. (around New Year’s Day) , 5 p.m. – 10 p.m. (Check website for updated dates/times.)

Enjoy this leisurely drive along the Chesapeake Bay while enjoying more than 60 animated and stationary light displays, sure to put a smile on every passenger’s face. And don’t forget to pick up 3D glasses at the beginning of the scenic tour for a little extra dose of light show magic!

The event showcases Maryland history and also features a decidedly feline and canine flavor, with all proceeds benefitting the SPCA of Anne Arundel County. In fact, for two nights in mid-November, guests can buy special tickets for the Lights & Leashes event, where dogs and their humans are permitted to park their cars and walk through the brilliant light display.

Small Business Saturday

• Address : Throughout Annapolis and Anne Arundel County
• Dates: Saturday after Thanksgiving

Downtown Annapolis takes its small businesses seriously, hosting special events like Small Business Saturday to make sure local shop owners thrive.

Free parking is available all day, and the website gives a complete list of independent shops and what you can find there. We never miss a chance to pop into the HERE, a Pop Up Shop, to see what the owner has found (most from artists and makers!) that we just have to have.

Show Annapolis businesses that you appreciate their personalized attention, unique offerings and community spirit by patronizing them all day. It’s a great way to find one-of-a-kind gifts for everyone on your Christmas list!

Artist Sunday

• Dates: The Sunday after Thanksgiving

Why not follow up Small Business Saturday with a new tradition celebrating independent artists and creators of every stripe? Annapolis takes an active role in this national festivity with its multitude of art stores, galleries and performance venues.

Check the annual Facebook event page or the website of your favorite Maryland art space for a number of discounts and special events going on throughout the region.

Homestead for the Holidays

• Address : 743 W. Central Ave., Davidsonville
• Dates: Throughout December: live music on weekends through December (Check website for updated dates/times.)

Enter a truly enchanted wonderland with this home-decor store, nursery and greenhouse as it is decked out with dozens of beautiful Christmas trees of every size and shape. They also offer thousands of ornaments, innumerable lights, and everything you could need to make your own holiday scene.

For more than 30 years, Homestead’s famous model railroad will chug around the greenhouse as guests enjoy a hot chocolate and watch elves hard at work in Santa’s workshop. Live music and talking reindeer delight kids of all ages.

In the outside nursery, a fire pit roars as families pick out their own fragrant evergreens

Parade of Light—Car Parade & Menorah Lighting

• Address : Safeway parking lot, 2635 Housley Rd., Annapolis, MD
• Dates: Evening for the fourth day of Chanukah. (Check website for updated dates/times.)

Chabad Anne Arundel County offers entertaining events scheduled throughout Chanukah. But our favorite is the annual Menorah Car Parade on the fourth night of the Festival of Lights. All are welcome to join and even participate in the parade!

Participants should pull up by 5 p.m. to leave from Safeway, and drive to the Alex Haley Memorial with fun menorah decorations on their roofs. At 5:45 p.m., event organizers will kindle a giant Menorah and celebrate the miraculous holiday.

Drivers and spectators will receive chocolate gelt (coins), prepackaged latkes, and kits to help celebrate Chanukah (while supplies last).

Annual Kwanzaa Celebration

• Address : Banneker-Douglass Museum, 84 Franklin St., Annapolis, MD
• Dates: December (Check website for updated dates/times.)

This program is perfect whether you’re a long-time Kwanzaa celebrant or want to learn more about the seven-day African-American festival. Honor the seven principles of Kwanzaa through musical and spoken word performances, a lighting ceremony, an interactive gift-making session, and a discussion on the importance of community and intergenerational engagement.

You’ll also get the chance to meet with representatives of Black-owned businesses.

Midnight Madness Holiday Shopping

• Address : throughout downtown Annapolis
• Dates: The first three Thursdays in December— 4 p.m. – midnight on first two; third, 4 p.m. – 11 p.m.

On these special nights, the town is transformed into a winter wonderland as shops stay open late for shoppers who want to shop for unique gifts while supporting local businesses.

The event takes place along Main and West Streets, Maryland Avenue, State Circle and Dock Street. Pedestrians looking for deals or simply enjoying the lovely night are treated to live outdoor music from carolers and other musicians, refreshments and other entertainment.

Make sure not to miss Snowflake Alley, the holiday lights canopy and, of course, the City Christmas tree at Market Space.

Holiday Candlelight Stroll

• Address : Departs from Market House Park, Annapolis, MD
• Dates: Fridays and Saturdays in December, 7 p.m. – 9 p.m.

A guide in festive period attire leads guests along the centuries-old brick lined streets of Maryland’s capital city, lit by lanterns and candles and lavishly adorned for the holidays.

Visitors will be enchanted by charming and humorous stories of 18 th and 19 th century holiday traditions against the backdrop of colonial mansions, Victorian homes and quaint shops.

First Sunday Arts Holiday Market

• Address : Whitmore Park and W. Street between Church Cir. & Graduate Annapolis Hotel, Annapolis, MD
• Dates: First Sunday of each month; special holiday markets in Nov. and Dec. (Check website for updated dates/times.)

The city provides free parking for this cherished Annapolis event, allowing shoppers in search of quirky and unique gifts a leisurely browse through the creations of more than 50 local and regional artisans.

Diverse artists and booths offer everything from customize portraits and delicious-smelling candles to Christmas ornaments with a Maryland flair (plus, visit over a hundred more artists virtually on their website!).

Outdoor café seating and live music is provided for shoppers who need to take a break. It’s also a perfect day to visit the galleries and art shops of West Street, many of whom take part in the market with special events and deals.

A Celebration of Christmas 

• Address : Maryland Hall, 801 Chase St., Annapolis, MD
• Dates: Friday in December, 8 p.m. (Check website for updated dates/times.)

Each year, tickets sell out early for this enthralling evening featuring the Annapolis Chorale and Chamber Orchestra. Joining together in a one-night-only show to perform dozens of seasonal favorites that often end in standing ovations.

Ballet Theatre of Maryland presents The Nutcracker 

• Address : 801 Chase St., Annapolis, MD
• Dates: Nov/Dec., Saturdays at 7 p.m., Sundays at 1 p.m. and 4:30 p.m. (Check website for updated dates/times.)

This cherished holiday tale of a girl’s adventure alongside her unusual Christmas present is performed by the top-tier dancers of the prestigious Ballet Theatre of Maryland. Let the spellbinding music of Tchaikovsky and athleticism of the graceful dancers whisk you away to the whirling Kingdoms of Snow and Sweets.

Find more performances of The Nutcracker Ballet in Washington DC .

Handel’s Messiah at St. Anne’s

• Address : St. Anne’s Episcopal Church, 199 Duke of Gloucester St., Annapolis, MD
• Dates: Check site for December date

Live Arts Maryland presents one of the world’s best loved and most popular musical works, performed many times each Christmas since its completion in 1741.

A cherished Annapolis holiday tradition set in one of the city’s most beloved and iconic buildings, you’ll be treated to world-class soloists, the Chamber Orchestra and the Annapolis Chorale performing in a powerful holiday celebration. Guests can even sing along to some holiday carols at this family-friendly event.

Annapolis Symphony Orchestra – Holiday Pops

• Address : Maryland Hall For The Creative Arts, 801 Chase St., Annapolis, MD
• Dates: One night each December

This popular seasonal program features nearly two hours of holiday favorites by the Annapolis Symphony Orchestra. Fun for the whole family, the tickets sell out every year. Buy now!

Historic Annapolis Holiday Wreath and Gift Sale

• Address : 1 Martin St., Annapolis, MD
• Dates: November dates (Check website for updated dates/times.)

Place your orders early for festive holiday greens, tabletop trees, a special hand-painted ornament for each year and a curated selection of pre-wrapped gifts with a touch of Maryland charm.

Each wreath and tree is made by Historic Annapolis volunteers using greenery and plants from the William Paca Garden. Purchases benefit Historic Annapolis’ ongoing mission of education and preservation of the area’s colorful past.

Military Bowl

• Address : Navy-Marine Corps Memorial Stadium, 550 Taylor Ave., Annapolis, MD
• Dates: Late December (typically a 2 p.m. kickoff)

For some, it’s a winter tradition as cherished as Thanksgiving or Christmas: The Military Bowl. Benefitting the USO of Metropolitan Washington-Baltimore, the game pits two college football teams head-to-head: Atlantic Coast Conference against American Athletic Conference in an outstanding display of athleticism and spirit.

The fun begins before the kickoff, with a parade through historic downtown featuring musical acts, civic and youth groups, and the world-famous Budweiser Clydesdales. Then grab some concessions and take your seat for an energetic game sprinkled with special events to salute the military and their families.

The Grand Illumination

• Address : City docks near the Market House, Market Space, Annapolis, MD
• Dates: The Sunday after Thanksgiving, 5:30 p.m., festivities begin at 4 p.m. (Check website for updated dates/times.)

Annapolis makes a big party out of the annual lighting of the city’s Christmas tree, and you’ll want to join if you’re there. Event includes a show of carols and dancing, warm drinks and candy canes, and the arrival of Santa Claus to light the tree himself!

There is plenty of fun for children, including ornaments they can decorate. The Annapolis Jaycees will also be on site collecting toys and non-perishable foods to donate to families in need. 

A Colonial Yuletide

• Address : William Paca House & Garden, 186 Prince George St.; Hogshead, 43 Pinkney St. George St., Annapolis, MD
• Dates: First Saturday in December, 2 p.m. – 6 p.m.

Always a fun trip for visitors and residents, this Georgian red-brick mansion is preserved as it would have been in the 18 th century, when Paca signed the Declaration of Independence and became Maryland’s third governor.

During the holidays, celebrate the season as William, Mary and the household servants decorate the home and prepare for a traditional colonial Christmas.

With reservations, a docent will lead you through the first floor of the house and the 2-acre William Paca Garden. Continue toward good cheer at Pinkney Street’s “Hogshead Tavern.” Come party like it’s 1774!

Tour includes both sites. Timed entry offered hourly 2 p.m. – 5 p.m. Walk-ups will be accommodated as space permits . Reservations recommended.

Eastport Yacht Club Lights Parade 

• Address : Annapolis Harbor and Spa Creek, Annapolis Waterfront
• Dates: Second Saturday in December, 6 – 8 p.m.

Spectators gather each year to watch more than 30 brightly lit boats bedecked for the holiday season appearing in the night to parade through the Annapolis waterfront during this beloved annual event. Thousands of lights crafted into some very creative displays, stalwart boat crews and a crowd of jolly revelers make this a fun Christmas tradition for the entire family.

Inside tip: if you bring some non-perishable food to donate, you can get onto the Harbor Queen cruise ship for free to watch the show in style!

Dining with the Loockermans

• Address : Hammond-Harwood House , 19 Maryland Ave., Annapolis, MD 
• Dates: Mid-December (Check website for updated dates/times.)

The curator and food historian of this William Buckland-built estate discuss the cooking and dining traditions of the house’s 19 th century residents, both free and enslaved.

Visitors are able to savor some historically accurate treats during the hour-long tour through the stately home’s kitchen, breakfast area and dining room. Reservations are required, and often visitors can pick a daytime or evening candlelight tour.

Jane Austen Tour

• Address : Hammond-Harwood House , 19 Maryland Ave., Annapolis, MD   

The booklover in your group will adore this spotlight tour of the historic, Christmas-decorated Hammond-Harwood House, which compares the customs and social graces of the Loockerman family (residents of the red-brick mansion during the early 19th century) with those in Jane Austen’s novels.

It’s a surprisingly affordable way to spend a holiday afternoon feeling posh and proper.

Lights Parade Dinner & Dessert Cruise

• Address : Begins at Severn Inn, 1993 Baltimore Annapolis Blvd., Annapolis, MD

Dine in style at the Severn Inn before enjoying a dessert aboard Watermark’s luxury yacht, Catherine Marie, as you watch the spectacular annual Eastport Yacht Club Lights Parade on the water. The yacht offers two levels, with double the bar service and convenient, buffet-style desserts so your family can appreciate the parade in comfort.

Tickets include a starter, entrée, dessert and a glass of champagne, as well as the inn and cruise experience.

Santa Speedo Run

• Address : O’Brien’s Oyster Bar & Seafood Tavern, 113 Main St.Annapolis, MD
• Dates: One Saturday in December, 11 a.m. – 3 p.m. (Check website for updated dates/times.)

Get in your holiday-style skivvies on this fun run/stroll through Annapolis. With a mission to spread holiday cheer and help local charities, participants should register early to be guaranteed a spot and t-shirt.

Bring your donated toy(s) at 11:00 a.m., then gather out front for caroling, pictures and the event. After-party kicks off at 12:30 p.m. with live music!

Additional reporting by Shannon K. Pennell and Heather Mundt

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Keryn Means