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Holiday events next month in Chestertown, MD

Search for something you love or check out popular events in your area.

Jingle & Mingle With Santa
Sun, Dec 14, 1:00 PM + 3 more
Joppatowne · The Great Hall at The Millstad Center
Jingle & Mingle With Santa
Sun, Dec 14, 1:00 PM + 3 more
Joppatowne · The Great Hall at The Millstad Center
Santa Brunch with Friends • DEC 6, 13, & 20
Sat, Dec 6, 10:00 AM + 5 more
Chesapeake City · Chesapeake Inn Restaurant & Marina
Santa Brunch with Friends • DEC 6, 13, & 20
Sat, Dec 6, 10:00 AM + 5 more
Chesapeake City · Chesapeake Inn Restaurant & Marina
Annapolis Chocolate Binge Festival 2025
Sun, Dec 7, 11:00 AM
Annapolis · 53 West St
Annapolis Chocolate Binge Festival 2025
Sun, Dec 7, 11:00 AM
Annapolis · 53 West St
Create your own Holiday Centerpiece
Sat, Dec 6, 11:00 AM
Churchville · Homelands Market
Create your own Holiday Centerpiece
Sat, Dec 6, 11:00 AM
Churchville · Homelands Market
Holiday Wreath Making Workshop
Sat, Dec 6, 10:00 AM
Severna Park · 670 Ritchie Hwy
Holiday Wreath Making Workshop
Sat, Dec 6, 10:00 AM
Severna Park · 670 Ritchie Hwy
Hat Burning Workshop at the Fallston Barrell House
Wed, Dec 10, 6:00 PM
Fallston · Fallston Barrel House
Hat Burning Workshop at the Fallston Barrell House
Wed, Dec 10, 6:00 PM
Fallston · Fallston Barrel House
4th Annual Holiday Party Cellar2
Sat, Dec 20, 8:30 PM
Baltimore · 7631 Harford Rd
4th Annual Holiday Party Cellar2
Sat, Dec 20, 8:30 PM
Baltimore · 7631 Harford Rd
Breakfast With Santa (Two Dates - December 13 & 14, 2025)
Sat, Dec 13, 9:00 AM + 1 more
White Marsh · White Marsh Volunteer Fire Company
Breakfast With Santa (Two Dates - December 13 & 14, 2025)
Sat, Dec 13, 9:00 AM + 1 more
White Marsh · White Marsh Volunteer Fire Company
436 MXS Western Holiday
Sat, Dec 6, 6:00 PM
Dover · Dover Elks Lodge
436 MXS Western Holiday
Sat, Dec 6, 6:00 PM
Dover · Dover Elks Lodge
Velvet Vibes: A Holiday Couples Networking Connection Experience
Sat, Dec 20, 5:00 PM
Baltimore · Hope & Wellness Healing Center
Velvet Vibes: A Holiday Couples Networking Connection Experience
Sat, Dec 20, 5:00 PM
Baltimore · Hope & Wellness Healing Center
SOD-O Holiday Party
Sat, Dec 6, 6:00 PM
Annapolis · Acqua al 2 - Annapolis
SOD-O Holiday Party
Sat, Dec 6, 6:00 PM
Annapolis · Acqua al 2 - Annapolis
It's All About the Children: Kwanzaa Celebration
Fri, Dec 26, 6:00 PM
Baltimore · 2100 Ashland Ave
It's All About the Children: Kwanzaa Celebration
Fri, Dec 26, 6:00 PM
Baltimore · 2100 Ashland Ave
EXP Maryland Agent Baltimore Holiday Luncheon
Tue, Dec 16, 3:00 PM
Baltimore · 901 Fawn St
EXP Maryland Agent Baltimore Holiday Luncheon
Tue, Dec 16, 3:00 PM
Baltimore · 901 Fawn St
Canton’s Official Santa Bar Fest
Sat, Dec 13, 12:00 PM
Baltimore · 1021 S Linwood Ave
Canton’s Official Santa Bar Fest
Sat, Dec 13, 12:00 PM
Baltimore · 1021 S Linwood Ave
A Merry Holiday Celebration
Sun, Dec 7, 4:00 AM
Dover · Dover Middle School Campus
A Merry Holiday Celebration
Sun, Dec 7, 4:00 AM
Dover · Dover Middle School Campus
The Worthington's Bad Santa Day Party
Sat, Dec 13, 12:00 PM
Baltimore · 2900 O'Donnell St
The Worthington's Bad Santa Day Party
Sat, Dec 13, 12:00 PM
Baltimore · 2900 O'Donnell St
20th Annual Christmas Party Coming Soon
Sat, Dec 20, 8:00 PM
Baltimore · Renaissance Baltimore Harborplace Hotel
20th Annual Christmas Party Coming Soon
Sat, Dec 20, 8:00 PM
Baltimore · Renaissance Baltimore Harborplace Hotel
New Year’s Interlude
Wed, Dec 31, 9:00 PM
Baltimore · Motte Restaurant & Bar
New Year’s Interlude
Wed, Dec 31, 9:00 PM
Baltimore · Motte Restaurant & Bar
New Year's Interlude
Wed, Dec 31, 9:00 PM
Baltimore · Motte Restaurant & Bar
New Year's Interlude
Wed, Dec 31, 9:00 PM
Baltimore · Motte Restaurant & Bar
NYE 2026
Wed, Dec 31, 9:00 PM
Baltimore · Renaissance Baltimore Harborplace Hotel
NYE 2026
Wed, Dec 31, 9:00 PM
Baltimore · Renaissance Baltimore Harborplace Hotel

Trends in Chestertown

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Frequently asked questions about Chestertown

What are the best events to attend next month?

According to Eventbrite, the best events next month are:

Jingle & Mingle With Santa

Annapolis Chocolate Binge Festival 2025

Hat Burning Workshop at the Fallston Barrell House

4th Annual Holiday Party Cellar2

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Santa Brunch with Friends • DEC 6, 13, & 20

Holiday Wreath Making Workshop

Create your own Holiday Centerpiece

436 MXS Western Holiday