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Events and Things to do in Chestertown, MD

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Dickens Holiday Home Tour
Sat, Dec 5, 10:00 AM
Chestertown · The Bank
Dickens Holiday Home Tour
Sat, Dec 5, 10:00 AM
Chestertown · The Bank
Dickens Victorian Tea
Sat, Dec 5, 1:00 PM
Chestertown · Christ United Methodist Church
Dickens Victorian Tea
Sat, Dec 5, 1:00 PM
Chestertown · Christ United Methodist Church
Waterman's Crab House 80's Murder Mystery Dinner & Show
Friday at 6:00 PM
Rock Hall · 21055 W Sharp St
Waterman's Crab House 80's Murder Mystery Dinner & Show
Friday at 6:00 PM
Rock Hall · 21055 W Sharp St
Selling fast
A Taste of Ireland - The Irish Music & Dance Sensation
Wed, Feb 17, 7:30 PM
Wye Mills · The Rufus M. and Loraine Hall Todd Performing Arts Center
Selling fast
A Taste of Ireland - The Irish Music & Dance Sensation
Wed, Feb 17, 7:30 PM
Wye Mills · The Rufus M. and Loraine Hall Todd Performing Arts Center
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
Sales end soon
Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
Selling fast
2026 Queen Anne's County Harvest Breakfast
Friday at 7:30 AM
Wye Mills · Chesapeake College - Caroline Center
Selling fast
2026 Queen Anne's County Harvest Breakfast
Friday at 7:30 AM
Wye Mills · Chesapeake College - Caroline Center
2026 Bourbon Classic Charity Clay Shooting Tournament
Wed, Nov 18, 9:00 AM
Queenstown · The Point at Pintail
2026 Bourbon Classic Charity Clay Shooting Tournament
Wed, Nov 18, 9:00 AM
Queenstown · The Point at Pintail
Dan Paisley & The Southern Grass
Sat, Nov 14, 7:00 PM
Chestertown · Chestertown Volunteer Fire Co
Dan Paisley & The Southern Grass
Sat, Nov 14, 7:00 PM
Chestertown · Chestertown Volunteer Fire Co
Thanksgiving Brunch at Kent Island Resort
Thu, Nov 26, 10:00 AM + 1 more
Stevensville · Kent Island Resort
Thanksgiving Brunch at Kent Island Resort
Thu, Nov 26, 10:00 AM + 1 more
Stevensville · Kent Island Resort
Breakfast With Santa Saturday December 19, 2026
Sat, Dec 19, 8:30 AM + 1 more
White Marsh · White Marsh Volunteer Fire Company
Breakfast With Santa Saturday December 19, 2026
Sat, Dec 19, 8:30 AM + 1 more
White Marsh · White Marsh Volunteer Fire Company
Sales end soon
Eastern Shore Business Connections Holiday Happy Hour
Thu, Nov 19, 5:00 PM
Grasonville · Bridges Restaurant on Kent Narrows
Sales end soon
Eastern Shore Business Connections Holiday Happy Hour
Thu, Nov 19, 5:00 PM
Grasonville · Bridges Restaurant on Kent Narrows
Thanksgiving Grand Buffet at Bohemia Manor Farm
Thu, Nov 26, 12:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Thanksgiving Grand Buffet at Bohemia Manor Farm
Thu, Nov 26, 12:00 PM
Chesapeake City · 237 Bohemia Manor Farm Ln
Sales end soon
One Piece TCG Modified Standard: EB05 Heroines Battle Vol. 2 Events
Monday at 6:45 PM
Abingdon · Critical Hit Games
Sales end soon
One Piece TCG Modified Standard: EB05 Heroines Battle Vol. 2 Events
Monday at 6:45 PM
Abingdon · Critical Hit Games
Selling fast
Costa's Paint Night
Tuesday at 6:00 PM
Baltimore · Costas Inn
Selling fast
Costa's Paint Night
Tuesday at 6:00 PM
Baltimore · Costas Inn
Sales end soon
Bohemia Manor Winery: Tour and Taste
Tomorrow at 12:00 PM + 25 more
Chesapeake City · 237 Bohemia Manor Farm Ln
Sales end soon
Bohemia Manor Winery: Tour and Taste
Tomorrow at 12:00 PM + 25 more
Chesapeake City · 237 Bohemia Manor Farm Ln
LoonASea Paint Night
Thu, Dec 3, 6:00 PM
Essex · LoonAsea Restaurant
LoonASea Paint Night
Thu, Dec 3, 6:00 PM
Essex · LoonAsea Restaurant
Sales end soon
Riftbound TCG Nexus Night Tournaments
Tuesday at 6:30 PM + 7 more
Abingdon · Critical Hit Games
Sales end soon
Riftbound TCG Nexus Night Tournaments
Tuesday at 6:30 PM + 7 more
Abingdon · Critical Hit Games
The Marsa Girls Pajama Party Drag Show: Sparrows Point
Sat, Nov 21, 6:00 PM
Sparrows Point · Marsā Coastal Kitchen
The Marsa Girls Pajama Party Drag Show: Sparrows Point
Sat, Nov 21, 6:00 PM
Sparrows Point · Marsā Coastal Kitchen
One Piece TCG: The Dominance of God OP18 Release Events
Sat, Nov 21, 6:45 PM + 2 more
Abingdon · Critical Hit Games
One Piece TCG: The Dominance of God OP18 Release Events
Sat, Nov 21, 6:45 PM + 2 more
Abingdon · Critical Hit Games
Selling fast
PCBT's The Nutcracker: December 5, 2026
Sat, Dec 5, 2:00 PM
Clayton · Providence Creek Ballet Theater
Selling fast
PCBT's The Nutcracker: December 5, 2026
Sat, Dec 5, 2:00 PM
Clayton · Providence Creek Ballet Theater

Trends in Chestertown

Explore more trends

Explore more trends

Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

Dickens Holiday Home Tour

Dickens Victorian Tea

Waterman's Crab House 80's Murder Mystery Dinner & Show

A Taste of Ireland - The Irish Music & Dance Sensation

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

halloween events

rocky horror picture show

Which events are coming up?

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

Bohemia Manor Winery: Tour and Taste

One Piece TCG Modified Standard: EB05 Heroines Battle Vol. 2 Events

Costa's Paint Night

Riftbound TCG Nexus Night Tournaments