Christmas Events for Kids in Annapolis (2026)

Christmas Events for Kids
Written by Kelsey Cecil

Updated 5 min read

Looking for Christmas events in Annapolis this year? We found 4 for kids and families in 2026, including Eastport Yacht Club Lights Parade, Lights on the Bay and Annapolis Gingerbread Houses. 1 of them is free. We check every date on the host’s own website, and each listing links straight there. For the rest of the state, see our Maryland Christmas events for kids guide.

The short version

  • 4 Christmas events for kids in Annapolis
  • The season runs from Annapolis Gingerbread Houses (Annapolis, November 21) to Annapolis Gingerbread Houses (through January 6)
  • Free: Eastport Yacht Club Lights Parade
  • Every date checked on the host’s own site on Nov 4

Christmas events for kids in Annapolis

4 events in Annapolis itself, soonest first.

Holiday crafts

Annapolis Gingerbread Houses

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Local bakers and community groups build gingerbread houses, and the finished creations are shown at the Annapolis Visitor Center from Nov 21 through Jan 6. Visitors can vote for the house they like best, which gives children an easy activity while the grown-ups browse.

The tourism board lists it alongside other seasonal outings in the area, including the North Pole Lights Walk and the Lights on the Bay drive at Sandy Point State Park. The page also notes that eligible downtown parking meters are free for the first three hours between Thanksgiving and New Year's Day, which helps with a short stop.

Parent tip: Check the Visitor Center's hours before you go, as they are not on the holiday page. Pair it with a walk downtown.

Host
Visit Annapolis & Anne Arundel County (opens in a new tab)
Address
Annapolis Visitor Center, 26 West St, Annapolis, MD 21401 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Visit Annapolis & Anne Arundel County (opens in a new tab)

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Rally’s Christmas research

Rally the corgi has 3 more Annapolis events researched for you.

  • New events every week We research new events daily and send you one email a week with the new ones we find in Annapolis.
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  • Rally’s Christmas Eve Express and a free advent calendar Get early access to Rally the corgi’s Christmas Eve tracker, plus a free digital advent calendar to count down to Christmas.
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Coming up on this page

  • 3 Lights
  • 2 Crafts
  • 1 Parades
  • 1 Markets
  • 1 Free

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Holiday lights

Lights on the Bay

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Families drive a two mile route along the water at Sandy Point State Park and pass more than 70 animated holiday light displays. Because everyone stays in the car, it suits toddlers, sleepy kids and cold evenings.

The Annapolis tourism board lists the run as November 23, 2026 through January 3, 2027. The page describes entry as a per-vehicle fee but does not give the amount, the nightly hours or any closed dates, so check the park's own information before heading out.

Parent tip: Fill up the car with snacks and blankets since you stay in the vehicle. Expect longer lines on weekends and the days near Christmas.

Host
Sandy Point State Park (via Visit Annapolis) (opens in a new tab)
Address
Sandy Point State Park, 1100 E College Pkwy, Annapolis, MD 21409 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Sandy Point State Park (via Visit Annapolis) (opens in a new tab)

New Annapolis events every week

Rally researches Christmas events in Annapolis daily and updates this page with new events. Enter your email to get a weekly update with new events in Annapolis.

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Holiday lights

Annapolis Chocolate Binge Festival

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The first block of West Street closes to traffic for an afternoon of chocolate vendors, restaurant specials and holiday shopping. Live bands and choirs perform from 11 am until the street's overhead light canopy turns on around 4 pm.

Kids can toast s'mores at the Scouts fire pit and help vote for a favorite entry in the Great Annapolis Gingerbread House contest at the Visitor Center on West Street, where winners are named at 3:30 pm. Chocolate samples need sample tickets, sold in bundles. A few add-on experiences, such as a baking demonstration and a spirits tasting, are separately ticketed.

Parent tip: Children under 12 do not need a ticket. The spirits tasting is for adults, so skip that add-on with little ones.

Host
Inner West Street Association (opens in a new tab)
Address
West Street (first block), West Street, Annapolis, MD 21401 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Inner West Street Association (opens in a new tab)

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Holiday paradeFree

Eastport Yacht Club Lights Parade

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Members of the Eastport Yacht Club decorate their boats with lights and cruise the harbor in a tradition that has run for about 40 years. The parade is free to watch, though local tour operators sell seats on cruise boats for people who want to see it from the water.

The tourism board suggests several land viewing spots: the Annapolis city front, the Spa Creek Bridge, the end of any downtown street that meets the water, and the pocket parks in Eastport and Murray Hill. A start time was not posted on the page when checked.

Parent tip: Pack a thermos of cocoa and warm layers, and pick a viewing spot early since waterfront rails fill up. Confirm the start time before you go.

Host
Eastport Yacht Club (via Visit Annapolis) (opens in a new tab)
Address
Annapolis City Dock and Spa Creek, 1 Dock Street, Annapolis, MD 21401 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Eastport Yacht Club (via Visit Annapolis) (opens in a new tab)

New Annapolis events every week

Rally researches Christmas events in Annapolis daily and updates this page with new events. Enter your email to get a weekly update with new events in Annapolis.

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Look inside the book

Story time with Santa in Annapolis? Bring Rally home.

A five-minute rhyming picture book about a corgi’s first train ride, painted in real watercolor. Turn a few pages now, then save it for bedtime after a big day with Santa.

Page 1 of 8

Rally Takes the Train book cover: a watercolor corgi peeking from a red train

Like it so far? See the full book

25 hand-painted pages, paperback, $16.99 with fast shipping from Amazon.

Buy on Amazon (opens in a new tab)

Every page is real watercolor on paper, painted by hand by Leslie Dunn. Nothing in this book was made with AI.

We check every event above on the host’s own page for the date, time and cost, plus the things parents ask about, like sign-ups and ages. Looking for a Santa train instead? Those are on our Maryland Christmas train rides page.

Annapolis Christmas events for kids at a glance

Kids’ Christmas events
4 confirmed for 2026
Cities
Annapolis
Season
November 21, 2026 to January 6, 2027
Free events
1
Kinds of events
Holiday lights, holiday crafts and holiday parades
Last checked
See every event on a December calendar

Plan your December

When each Annapolis Christmas event for kids happens

The first is Annapolis Gingerbread Houses in Annapolis on November 21; the last runs to January 3. Each bar spans an event’s dates, not every hour in them, so check the host’s page for times.

Looking further afield? Our Maryland Christmas events for kids guide lists every confirmed event in the state, and we have city guides for Baltimore, Frederick, Gaithersburg, Bowie and Germantown. The national search sorts every event by distance from your town.

A story for the drive home

A morning with Santa or an evening of holiday stories tends to end the same way: tired kids, a long drive and one more book before bed. Our picture book follows Rally the corgi on his first train ride to see his grand-paw-rents, and every page is painted by hand. If your family is spending December missing someone, it was written for that too. For the car, print our free corgi and train coloring pages.

Rally Takes the Train book cover: a watercolor corgi peeking from a red train

A bedtime story after seeing SantaRally Takes the Train is a five-minute rhyming picture book about a corgi’s first ride on a California train, hand-painted in watercolor. $16.99 on Amazon, ages 0 to 8.

Buy on Amazon (opens in a new tab)

2026 Christmas events are coming in late November

More Christmas events arrive in late November. We add them here as soon as we confirm them.

The story of Christmas in Annapolis

In Annapolis, Christmas started with a few sailors singing carols from their boats. Today, dozens of lit-up boats parade through the harbor each December while tens of thousands of people watch from the shore.

How Annapolis celebrates

The Eastport Yacht Club Lights Parade is the city's best-known Christmas tradition. It grew out of the club's early days in the 1980s, when members who lived aboard their boats sailed around the harbor one December singing carols. Later they added lights, and by 1986 about 15 to 20 boats made it an official parade. Today the fleet splits in two, with one group circling Ego Alley and downtown while the other sails up Spa Creek, and the groups swap places when the Spa Creek bridge opens. In 1988 it was named the official Maryland Winter Celebration.

Christmas last year in Annapolis

On Saturday, December 13, 2025, the 43rd annual Eastport Yacht Club Lights Parade returned to Annapolis Harbor. Dozens of decorated boats of all sizes, from classic yachts to fishing boats and small skiffs, cruised the waterfront for two hours, and tens of thousands of spectators came to watch. Families watched from the Annapolis city front, the Spa Creek Bridge, the ends of downtown streets that meet the water, and the Eastport and Murray Hill pocket parks. There is no entry fee for boats, and skippers meet the Thursday before.

Fun facts about Christmas in Annapolis

The parade's busiest year was 1988, with 65 registered boats in three fleets. In the late 1980s, two 45-foot sloops were turned into square riggers. In 2001, the parade hosted its first wedding and its first proposal. Past winners include a powerboat styled as the Griswold family station wagon, a sailboat with an abominable snowman and a boat with reindeer pulling a dinghy carrying Santa. In 2022, about 30,000 spectators watched, and a 75-foot skipjack from the Annapolis Maritime Museum joined the fleet.

Trains and Christmas near Annapolis

Annapolis is best known for boats, but train fans have good museums nearby. Bowie Railroad Museum is a free city museum built around a restored railroad station and a 1923 caboose. Chesapeake Beach Railway Museum, in the original 1898 depot, tells the story of the resort and rail line that founded its town. Farther north, the Baltimore Streetcar Museum runs Santa's Streetcar on December weekends, with unlimited rides on restored Baltimore streetcars.

Traditions today

  • Eastport Yacht Club Lights Parade: Decorated boats parade through Annapolis Harbor and Spa Creek on a December evening, a tradition since the early 1980s.
  • Boat decorating contest: Judges give awards in several categories, and skippers spend days dressing up their boats.
  • Annapolis Holiday Market: A free holiday market at City Dock with artisans and vendors, which had 120 of them in 2024.
  • Holiday by the Bay: The Naval Academy Band plays a free holiday concert at the Main Chapel in December.
  • Handel's Messiah at St. Anne's: The Annapolis Chorale Chamber Chorus and Annapolis Chamber Orchestra perform the Messiah at St. Anne's Episcopal Church.
  • The Nutcracker: Ballet Theatre of Maryland performs The Nutcracker at Maryland Hall each December.

A fact for kids

Annapolis' famous Christmas parade began with a few sailors who sang carols from their boats, and now boats dress up as station wagons, snowmen and Santa's sleigh.

Questions about Christmas in Annapolis

How did the Annapolis Christmas boat parade start?

It started with carols. In the early days of the Eastport Yacht Club, which began in 1980, some members lived aboard boats in the marina and one December sailed around the harbor singing Christmas songs. They then added lights, and by 1986 it was an official parade of 15 to 20 boats.

How old is the Eastport Yacht Club Lights Parade?

The 2025 parade was billed as the 43rd annual, so it began in the early 1980s. Sources differ slightly on the exact first year, and a Chesapeake Bay Magazine story says it began in 1981 when a boat owner hung lights in his rigging. It became an official parade in 1986.

What happened at the Annapolis Lights Parade last year?

On Saturday, December 13, 2025, dozens of decorated boats of all sizes cruised the Annapolis waterfront for two hours in the 43rd annual parade. Tens of thousands of spectators watched from the shore. Boats ranged from classic yachts to fishing boats and small skiffs.

How many people watch the Annapolis Lights Parade?

Tens of thousands of people watch. A 2025 report said the parade draws tens of thousands of spectators, and a 2022 article counted about 30,000 around the harbor. Many families pick a spot early at City Dock or the Spa Creek Bridge, so it is smart to arrive well before dark with little ones.

Where is the best place to watch the Annapolis boat parade?

Good spots include the Annapolis city front, Spa Creek Bridge, City Dock, the end of any downtown street that meets the water, and the Eastport and Murray Hill pocket parks. See our Annapolis Christmas events guide on this page for this year's details.

How do the boats in the Annapolis parade pass under the bridge?

The fleet is split in two. One fleet circles Ego Alley and downtown, and the other sails up Spa Creek, then they swap when the Spa Creek bridge opens. This lets the city keep traffic moving, and the bridge now stays open about 15 to 20 minutes instead of an hour and a half as in 1986.

Can any boat join the Annapolis Lights Parade?

Yes. Any kind of boat can enter, whether sail, power or dinghy, and entrants do not need to be club members. There is no entry fee, but skippers register online and attend a meeting the Thursday before. Decorations are the main requirement, and safety comes first at night on the water.

What are some silly boats from past Annapolis parades?

Past winners include a powerboat styled as the Griswold family station wagon, a sailboat with an abominable snowman, and a boat with reindeer pulling a dinghy carrying Santa. In the late 1980s, two 45-foot sloops were turned into square riggers. A boat shaped like a leg lamp has also floated by.

Has anyone gotten engaged at the Annapolis boat parade?

Yes. In 2001, the parade hosted its first wedding and its first proposal, according to a Chesapeake Bay Magazine story on the parade's history. It is one of the more surprising moments in a long list of parade milestones. Kids will enjoy hearing that a wedding once took place during the parade.

What was the busiest year for the Annapolis boat parade?

The busiest year was 1988, when 65 registered boats sailed in three fleets. That was also the year the parade was named the official Maryland Winter Celebration. In more recent years, organizers have said it can be a struggle to reach 40 boats, though dozens still take part.

What does the Annapolis Lights Parade win in contests?

Boats compete for prizes in several categories, and the parade has been ranked ninth on a USA Today list of best holiday parades, according to a 2024 report. In 2021, Best in Show went to a sailboat with a palm tree mast and a Pirate's Treasure Island theme.

What are the Chief Elves in Annapolis?

The parade's volunteer organizers are called elves. Heather Ersts was Chief Elf from 2005 to 2008, and Tom and Trudy Stalder were Co-Chief Elves for four years. The event even has a Safety Elf. Kids like hearing that real elves help plan a parade of boats.

Has the Annapolis Lights Parade ever been canceled?

Yes, a few times. It was canceled in 2020 because of the pandemic, and in 2021 it was called off on the day because of forecast high winds. In 1991, a cold front with gusts up to 48 mph hit just before the start, but the parade went ahead anyway.

How can I explain the boat parade to my toddler?

Tell them that in Annapolis, boats dress up for Christmas with lights, just like houses. At night the boats sail slowly through the harbor like a parade on the water. Pointing out snowmen, reindeer and Santa on the boats makes it a fun spotting game from the shore.

What is the Annapolis Holiday Market?

It is a free holiday market at City Dock, open in December. In 2024 it featured 120 artisans and vendors. It is a good place for families to browse handmade gifts before or after watching the boats. Check our Annapolis Christmas events guide on this page for this year's hours.

Are there Christmas concerts in Annapolis?

Yes. In December 2024, the Naval Academy Band offered a free Holiday by the Bay concert at the Main Chapel, the Annapolis Chorale performed Handel's Messiah at St. Anne's Episcopal Church, and Ballet Theatre of Maryland staged The Nutcracker at Maryland Hall. Dates and tickets change each year.

Where can kids see trains near Annapolis at Christmas?

Bowie Railroad Museum, a free city museum in Old Town Bowie, has a restored station and a 1923 caboose and is open weekends. The Baltimore Streetcar Museum runs Santa's Streetcar on December weekends. Check each museum's hours before you go. Our Annapolis Christmas events guide on this page also lists seasonal rides.

Is there a train museum near Annapolis?

Yes. Chesapeake Beach Railway Museum sits in the original 1898 depot of the Chesapeake Beach Railway and is free, open daily 1 to 4 p.m., April through October. Bowie Railroad Museum is also nearby and open on weekends. Both are good fits for families who love old trains and depots.

Is there a Christmas parade in Annapolis this year?

Annapolis holds its Eastport Yacht Club Lights Parade each December, usually on the second Saturday, and the date listed for 2026 is December 12. For confirmed times, watching spots and boat tours, see our Annapolis Christmas events guide on this page.

Where can kids see Christmas lights in Annapolis?

The best Christmas lights in Annapolis are on the water. Boats cross the harbor and Spa Creek in the lights parade, and families watch from City Dock, the Spa Creek Bridge and the pocket parks in Eastport. Our Annapolis Christmas events guide on this page lists this season's confirmed dates.

Sources

  1. Behind the Mask: Tom Stalder, the History of the EYC Lights Parade, Visit Annapolis
  2. Eastport Yacht Club Lights Parade, Visit Annapolis
  3. Eastport Yacht Club Lights Parade returns for 43rd year on December 13, Ground News
  4. Sharing the Light, Chesapeake Bay Magazine
  5. Parade of lights, ballet, Nutcracker, Handel's Messiah, holiday pops, The Baltimore Banner
  6. Bowie Railroad Museum, Rally Takes the Train
  7. Chesapeake Beach Railway Museum, Rally Takes the Train
  8. Baltimore Streetcar Museum, Rally Takes the Train

Keep the Christmas magic going: follow Rally's Christmas Eve Express, print printable Rally coloring pages, learn Merry Christmas in 100+ languages, find train museums near you, or browse Christmas events in every Maryland city.

Annapolis Christmas events for kids: questions parents ask

What are the best Christmas events for kids in Annapolis this year?

Rally Takes the Train has confirmed 4 Christmas events for kids in Annapolis for the 2026 season, and 1 of them are free. Good places to start: Eastport Yacht Club Lights Parade (Dec 12), Lights on the Bay (Nov 23 to Jan 3) and Annapolis Gingerbread Houses (Nov 21 to Jan 6). Each one is listed with its dates, times, cost and a link to the host.

Are there free Christmas events for kids in Annapolis?

Yes. 1 of the 4 Christmas events for kids in Annapolis confirmed for 2026 are free. Some free events still need a reservation, so check the host’s page before you go.

Where can kids see Christmas lights in Annapolis?

There are three Christmas light displays and tree lightings in and around Annapolis this year, including Annapolis Chocolate Binge Festival (Dec 6). Most light walks run on set evenings only, so check the host’s dates before you go.

Is anything on for kids in Annapolis on Christmas Eve or after Christmas?

Yes, two events run on Christmas Eve or later. Annapolis Gingerbread Houses runs through Jan 6 and Lights on the Bay runs through Jan 3.

Do we need tickets or reservations?

For 3 of the 4 Christmas events for kids in Annapolis, yes: they sell tickets or ask you to sign up ahead. Meals with Santa and ticketed shows fill up first. Most library and park events are walk-in.

Are there Christmas train rides for kids in Annapolis?

Yes. Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Maryland Christmas train rides guide. This Annapolis guide covers story times, Santa visits, light shows and other events off the rails.

How do you confirm these events?

We list an event only after we find this season’s date on the host’s own website or an official city or tourism calendar. We last checked every listing on November 4, 2026. Hosts change details, so always confirm on the host’s page before you go.

Event names belong to their hosts. Rally Takes the Train is a family picture book and is not affiliated with, sponsored by or endorsed by any host listed here. Confirm dates, times and prices on each host’s own site before you go.

Kelsey Cecil
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