Christmas Events for Kids in Chestertown (2026)

Christmas Events for Kids
Written by Kelsey Cecil

Updated 4 min read

Rally the corgi has sniffed out the best Christmas events for kids in Chestertown for 2026, and here is what he found: 2 family events. They are Dickens of a Christmas: A Christmas Carol Storytime (December 5) and Gingerbread Houses (December 10). 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.

What Rally found in Chestertown

  • 2 Christmas events for kids in Chestertown
  • Season: December 5 (Dickens of a Christmas: A Christmas Carol Storytime) to December 10 (Gingerbread Houses)
  • Every date checked on the host’s own site on Nov 10

Ticketed and paid Christmas events for kids in Chestertown

Admission, tickets or a fee apply. Where a host has not posted a price yet, the listing says so.

Holiday story time

Dickens of a Christmas: A Christmas Carol Storytime

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Kent County Public Library takes its story time on the road for Dickens of a Christmas, reading a children's version of A Christmas Carol aloud. The reading happens at the Garfield Center for the Arts on High Street rather than at the library, as one stop on the larger Dickens of a Christmas schedule.

The storytime is on Saturday, December 5, 2026, from 11:00 to 11:30 a.m. at the Garfield Center for the Arts, 210 High Street. The library lists it for all ages, with kids ages 5 to 8 and 9 to 12 named as the audience. The page does not mention a price or any sign-up.

Parent tip: This is an off-site library program, so head to the Garfield Center at 210 High Street and not the library branch on the same street. At only 30 minutes it is an easy stop for early readers before the rest of the Dickens of a Christmas schedule.

Host
Kent County Public Library (opens in a new tab)
Address
Garfield Center for the Arts, 210 High St, Chestertown, MD 21620 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Kent County Public Library (opens in a new tab)

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Rally’s Christmas research

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Coming up on this page

  • 1 Crafts
  • 1 Story time
  • 1 Breakfast and treats

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Holiday crafts

Gingerbread Houses

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Builders of every age put together a small house from graham crackers, which stand in for real gingerbread, then cover it in frosting, gumdrops, candy canes and other treats. Each person designs their own and takes it home. Kent County Public Library runs the same program at all three of its branches in December.

The library's listing gives the Chestertown session as Thursday, December 10, 2026, at 4:30 p.m., with limited space and registration required. The linked page is the sign-up for the North County branch session on Tuesday, December 8, which runs 4:30 to 5:30 p.m. and opens registration at 4:30 p.m. on November 17, so make sure you register for the Chestertown date. No price is listed.

Parent tip: The three branch sessions have separate sign-ups, and the library itself warns families to check they are registering for the right location. Pick the Chestertown listing for December 10, and bring a box or tray, since frosting needs time to set before the ride home.

Host
Kent County Public Library (opens in a new tab)
Address
Kent County Public Library, Chestertown Branch, 408 High St, Chestertown, MD 21620 (opens in maps)
Confirmed
On the host’s page, checked
See dates and detailsfrom Kent County Public Library (opens in a new tab)

New Chestertown events every week

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

Free. Unsubscribe anytime. Privacy policy (opens in a new tab)

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.

See every event on a December calendar

Plan your December

When each Chestertown Christmas event for kids happens

The first is Dickens of a Christmas: A Christmas Carol Storytime in Chestertown on December 5; the last runs to December 10. 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 event we have found in the state, and we have city guides for Annapolis, Severna Park, Brooklyn Park and Baltimore. 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 Chestertown

At the first United States census in 1790, Chestertown was the geographical center of the whole country's population, a port town at the navigable head of the Chester River. At Christmas the action is on High Street, where the public library reads A Christmas Carol to children during Dickens of a Christmas and families build gingerbread houses at the library branch.

How Chestertown celebrates

Kent County Public Library is the organizer behind both of this season's listings. During Dickens of a Christmas, the library leaves its building and reads a children's version of A Christmas Carol at the Garfield Center for the Arts at 210 High Street, the same street the town's Tea Party Festival parade follows down to the Chester River. Later in the week the library hosts Gingerbread Houses, a build-and-take-home program using graham crackers, frosting and candy that it offers at all three branches, including Chestertown. Sign-up is required for that one because space is limited.

Fun facts about Christmas in Chestertown

Chestertown was founded in 1706 and became one of colonial Maryland's six Royal Ports of Entry, and by the mid-1700s it was considered the colony's second leading port after Annapolis. It was incorporated in 1805 and named for the Chester River. Washington College, founded here in 1782 with George Washington as a founding patron, is the tenth oldest college in the United States. The 2020 census counted 5,532 residents.

Traditions today

  • A Christmas Carol storytime: Kent County Public Library reads a children's version of A Christmas Carol at the Garfield Center for the Arts during Dickens of a Christmas.
  • Gingerbread Houses at the library: Builders of all ages make graham cracker houses with frosting and candy at the Chestertown branch and take them home.
  • High Street: The Garfield Center for the Arts and the library branch both sit on High Street, the road that runs down to the Chester River.
  • The Chester River waterfront: Brick mansions and townhouses from the town's days as a colonial port still line the waterfront and frame a December walk.

A fact for kids

A wooden sailing ship called the schooner Sultana was built in Chestertown with help from more than 3,000 students. Over 10,000 people came to watch it launch in March 2001.

Questions about Christmas in Chestertown

When was Chestertown founded?

Chestertown was founded in 1706 and was incorporated in 1805. It grew quickly after being named one of the six Royal Ports of Entry for the English colony of Maryland, and the shipping trade that followed made the town wealthy.

How did Chestertown get its name?

The town was named for the Chester River. It sits at the navigable head of that river, which is why it became a busy colonial port. By the middle of the 1700s only Annapolis ranked ahead of it among Maryland ports.

How many people live in Chestertown?

The 2020 census counted 5,532 people. Chestertown is the county seat of Kent County, which is the oldest county in Maryland. The town covers about 2.91 square miles, and a little of that area is water.

What is Chestertown known for?

It is known for its colonial past. Chestertown is second only to Annapolis in its number of surviving eighteenth century homes, and each Memorial Day weekend the Chestertown Tea Party Festival re-enacts a legendary 1774 protest in which tea was thrown into the Chester River.

What college is in Chestertown?

Washington College, a private liberal arts college founded in 1782, is in Chestertown. It is the tenth oldest college in the United States, and George Washington was a founding patron. Its three early halls are listed on the National Register of Historic Places.

Did Chestertown have a railroad station?

Yes. The Chestertown Railroad Station is one of the town's historic properties listed on the National Register of Historic Places. Today the main way to reach town is by road, with Maryland Route 213 as the most important highway.

What happens at Christmas in Chestertown for kids?

This season the library offers two programs. A Christmas Carol storytime takes place on Saturday, December 5, 2026, during Dickens of a Christmas, and Gingerbread Houses comes to the Chestertown branch on Thursday, December 10, 2026, at 4:30 p.m.

Who organizes these Christmas events?

Kent County Public Library runs both. The storytime is an outreach program held away from the library at the Garfield Center for the Arts, and the gingerbread program is offered at all three library branches: North County, Rock Hall and Chestertown.

Where do Chestertown's Christmas events take place?

Both are on High Street. The Christmas Carol storytime is at the Garfield Center for the Arts at 210 High Street, and the gingerbread program is at the library's Chestertown branch. High Street is also the route of the Tea Party Festival parade to the river.

Do Chestertown's library Christmas programs cost anything?

Neither library page lists a price. Gingerbread Houses has limited space and requires registration, with a separate sign-up for each branch. The Christmas Carol storytime page shows no registration step, so families can plan to arrive at the Garfield Center by 11:00 a.m.

Sources

  1. Chestertown, Maryland, Wikipedia
  2. Dickens of a Christmas: A Christmas Carol Storytime, Kent County Public Library
  3. Gingerbread Houses, Kent County Public Library

Keep the Christmas magic going: track Rally the corgi on Christmas Eve, print free Christmas coloring pages, learn how to say Merry Christmas in 100+ languages, find train museums to visit with kids, or browse Christmas events in every Maryland city.

Chestertown Christmas events for kids: questions parents ask

What are the best Christmas events for kids in Chestertown to start with?

Start with the Dickens of a Christmas storytime on Saturday, December 5, 2026, when Kent County Public Library reads a children's version of A Christmas Carol at the Garfield Center for the Arts. Then sign up for Gingerbread Houses at the Chestertown library branch on Thursday, December 10.

Are there free Christmas events for kids in Chestertown?

Neither library page lists a price. The Christmas Carol storytime on December 5, 2026, shows no fee and no sign-up, and Gingerbread Houses on December 10 shows no fee but does require registration. The pages do not use the word free, so confirm with the library if cost matters.

Where can kids meet Santa in Chestertown?

The two Chestertown listings in this guide do not include a Santa visit. One is a story time held during Dickens of a Christmas on December 5, 2026, and the other is a gingerbread house workshop on December 10. Dickens of a Christmas has its own fuller schedule worth checking.

Is there a holiday story time in Chestertown?

Yes. On Saturday, December 5, 2026, from 11:00 to 11:30 a.m., Kent County Public Library reads a children's version of A Christmas Carol at the Garfield Center for the Arts, 210 High Street. It is listed for all ages, with kids 5 to 12 as the main audience.

Which Chestertown Christmas events need sign-up?

Gingerbread Houses does. The library says space is limited and registration is required, and each of its three branches has a separate sign-up. The Chestertown session is Thursday, December 10, 2026, at 4:30 p.m. The December 5 storytime page does not mention registration.

What is Dickens of a Christmas in Chestertown?

It is a Chestertown holiday event with its own schedule, and Kent County Public Library takes part with a Christmas Carol storytime on December 5, 2026. That reading is held on High Street at the Garfield Center for the Arts, in a town founded in 1706.

Are there Christmas train rides for kids near Chestertown?

Santa trains and holiday train rides have their own guide: Rally Takes the Train’s Maryland Christmas train rides guide. This Chestertown guide covers Santa visits, story times, 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 10, 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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