Best Christmas events in Leonardtown November 2025

Q: What are the upcoming Christmas events in Leonardtown?

Here are the upcoming events in Leonardtown: Christmas on the Square & Annual Tree Lighting, Small Business Saturday with The Grinch & Cindy Lou Who, Spin It Again at Christmas on the Square, Christmas on the Square 🎅🏼🧑🏼🎄, SANTA MINIS “Photos with Santa “2025”, Museum Store Sunday at the Old Jail Museum & Leonardtown Visitor Center

Q: Which kind of events are trending in Leonardtown?

Here are the top trending events in LeonardtownChristmas Wreath Workshops, 🎄 Christmas , Thanksgiving

Christmas events in Leonardtown in November

Fri, 28 Nov, 2025 - 04:30 PM

Christmas on the Square & Annual Tree Lighting

Town of Leonardtown

3556+ Interested
Sat, 29 Nov, 2025 - 09:00 AM

Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC

612+ Interested
Fri, 28 Nov, 2025 - 04:30 PM

Spin It Again at Christmas on the Square

Leonardtown Square
Fri, 28 Nov, 2025 - 04:30 PM

Christmas on the Square 🎅🏼🧑🏼‍🎄

Leonardtown Square

14+ Interested
Sat, 29 Nov, 2025 - 09:00 AM

SANTA MINIS “Photos with Santa “2025”

Starrella Photography by Aprilynn

36+ Interested
Sun, 30 Nov, 2025 - 10:00 AM

Museum Store Sunday at the Old Jail Museum & Leonardtown Visitor Center

Old Jail Museum - Leonardtown

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Christmas events from nearby cities

Wed, 31 Dec • 09:00 PM

Boudoir Bohéme Masquerade Ball

Secret Location

276+ Interested

|

USD 59
Sat, 13 Dec • 12:00 PM

🌟 🎄 2nd Annual Holiday Craft Fair & Toy Drive! 🎁 🎅

iLove Events Center

Free
Sat, 20 Dec • 02:00 AM

Bolly Xmas Virginia

Bole Bole Ethiopian Kitchen & Bar

Newly Added

|

USD 10
Sun, 14 Dec • 05:00 PM

Toys for Shelter Pets – Second Annual Christmas Charity Event

Hotel Hive

Newly Added

|

USD 15
Wed, 24 Dec • 09:00 PM

MATZOBALL® WASHINGTON DC XMAS EVE ages 21-49 December 24, 2025

Decades DC

Newly Added

|

USD 40
Fri, 05 Dec • 09:00 AM

Holiday Craft Show

2371 Carl D Silver Pkwy, Fredericksburg, VA, United States, Virginia 22401

5351+ Interested
Sat, 29 Nov • 09:00 AM

Old Town Manassas Christmas Market and Holiday Craft Show

Manassas Museum

2136+ Interested
Sat, 06 Dec • 05:30 PM

Official Fredericksburg Christmas Parade

Downtown Fredericksburg

5048+ Interested
Fri, 05 Dec • 07:30 PM

2025 Holiday Singles Gala

Crosswinds

10+ Interested

|

USD 319

Frequently Asked Questions

Which Christmas events can I attend in Leonardtown today?

Here are the best Christmas events happening in Leonardtown today:

Christmas on the Square & Annual Tree Lighting is happening on 28 Nov 2025 from 4:30 PM onwards at Town of Leonardtown
Spin It Again at Christmas on the Square is happening on 28 Nov 2025 from 4:30 PM onwards at Leonardtown Square
Christmas on the Square 🎅🏼🧑🏼‍🎄 is happening on 28 Nov 2025 from 4:30 PM onwards at Leonardtown Square

What are the upcoming Christmas events in Leonardtown?

Here are the upcoming Christmas events in Leonardtown:

Christmas on the Square & Annual Tree Lighting is happening on Fri 28 Nov 2025 from 4:30 PM onwards at Town of Leonardtown
Small Business Saturday with The Grinch & Cindy Lou Who is happening on Sat 29 Nov 2025 from 9:00 AM onwards at Town Market LLC, Leonardtown
Spin It Again at Christmas on the Square is happening on Fri 28 Nov 2025 from 4:30 PM onwards at Leonardtown Square
Christmas on the Square 🎅🏼🧑🏼‍🎄 is happening on Fri 28 Nov 2025 from 4:30 PM onwards at Leonardtown Square
SANTA MINIS “Photos with Santa “2025” is happening on Sat 29 Nov 2025 from 9:00 AM onwards at Starrella Photography by Aprilynn, Leonardtown
Museum Store Sunday at the Old Jail Museum & Leonardtown Visitor Center is happening on Sun 30 Nov 2025 from 10:00 AM onwards at Old Jail Museum - Leonardtown

Which kind of events are trending in Leonardtown?