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Events and Things to do in Chestertown, MD

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Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
Elegant Afternoon Tea at Brampton 1860
Sun, Nov 15, 2:00 PM + 1 more
Chestertown · 25227 Chestertown Rd
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
Waterman's Crab House 80's Murder Mystery Dinner & Show
Fri, Nov 13, 6:00 PM
Rock Hall · 21055 W Sharp St
Waterman's Crab House 80's Murder Mystery Dinner & Show
Fri, Nov 13, 6:00 PM
Rock Hall · 21055 W Sharp St
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
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
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
2026 Queen Anne's County Harvest Breakfast
Fri, Nov 13, 7:30 AM
Wye Mills · Chesapeake College - Caroline Center
2026 Queen Anne's County Harvest Breakfast
Fri, Nov 13, 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
Selling fast
Quarter Mania- Third Annual
Saturday at 6:30 PM
Abingdon · Abingdon Fire Company
Selling fast
Quarter Mania- Third Annual
Saturday at 6:30 PM
Abingdon · Abingdon Fire Company
Eastern Shore Business Connections Holiday Happy Hour
Thu, Nov 19, 5:00 PM
Grasonville · Bridges Restaurant on Kent Narrows
Eastern Shore Business Connections Holiday Happy Hour
Thu, Nov 19, 5:00 PM
Grasonville · Bridges Restaurant on Kent Narrows
Selling fast
Costa's Paint Night
Tue, Nov 10, 6:00 PM
Baltimore · Costas Inn
Selling fast
Costa's Paint Night
Tue, Nov 10, 6:00 PM
Baltimore · Costas Inn
Sales end soon
Kim Walker-Smith - A Night of Worship
Saturday at 7:00 PM
Perry Hall · 5125 E Joppa Rd
Sales end soon
Kim Walker-Smith - A Night of Worship
Saturday at 7:00 PM
Perry Hall · 5125 E Joppa Rd
Sales end soon
Magic Presents: Star Trek Prerelease
Friday at 7:00 PM
Abingdon · Critical Hit Games
Sales end soon
Magic Presents: Star Trek Prerelease
Friday at 7:00 PM
Abingdon · Critical Hit Games
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
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
Sales end soon
Riftbound TCG Nexus Night Tournaments
Tomorrow at 6:30 PM + 8 more
Abingdon · Critical Hit Games
Sales end soon
Riftbound TCG Nexus Night Tournaments
Tomorrow at 6:30 PM + 8 more
Abingdon · Critical Hit Games
Bohemia Manor Winery: Tour and Taste
Sun, Nov 8, 12:00 PM + 25 more
Chesapeake City · 237 Bohemia Manor Farm Ln
Bohemia Manor Winery: Tour and Taste
Sun, Nov 8, 12:00 PM + 25 more
Chesapeake City · 237 Bohemia Manor Farm Ln
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
PCBT's The Nutcracker: December 5, 2026
Sat, Dec 5, 2:00 PM
Clayton · Providence Creek Ballet Theater
PCBT's The Nutcracker: December 5, 2026
Sat, Dec 5, 2:00 PM
Clayton · Providence Creek Ballet Theater
The Landing Strip Paint Night
Mon, Dec 14, 6:00 PM
Middle River · The Landing Strip
The Landing Strip Paint Night
Mon, Dec 14, 6:00 PM
Middle River · The Landing Strip

Trends in Chestertown

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Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

Elegant Afternoon Tea at Brampton 1860

Dickens Holiday Home Tour

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

Dickens Victorian Tea

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

halloween events

Which events are coming up?

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

Riftbound TCG Nexus Night Tournaments

Magic Presents: Star Trek Prerelease

Quarter Mania- Third Annual

Kim Walker-Smith - A Night of Worship