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Events in Chestertown, MD

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

Maryland Commodity Classic 2025
Thu, Jul 24, 8:00 AM
Queen Anne's County 4-H Park
Maryland Commodity Classic 2025
Thu, Jul 24, 8:00 AM
Queen Anne's County 4-H Park
Washington College Field Hockey Summer Clinic
Sun, Jul 20, 10:00 AM
Washington College
Washington College Field Hockey Summer Clinic
Sun, Jul 20, 10:00 AM
Washington College
Going fast
Grape Expectations: A Playful Plates Party -Brampton 1860, Flavors of Spain
Thu, Jul 24, 6:00 PM
25227 Chestertown Rd
Going fast
Grape Expectations: A Playful Plates Party -Brampton 1860, Flavors of Spain
Thu, Jul 24, 6:00 PM
25227 Chestertown Rd
Lotus Paddle 2 - 2025 - Sultana Education Foundation
Sat, Aug 9, 9:00 AM
Turner's Creek
Lotus Paddle 2 - 2025 - Sultana Education Foundation
Sat, Aug 9, 9:00 AM
Turner's Creek
BBQ & BREWS | Get SAUCED at Piney Grove
Sat, Aug 2, 12:00 PM
Piney Grove
BBQ & BREWS | Get SAUCED at Piney Grove
Sat, Aug 2, 12:00 PM
Piney Grove
Almost full
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Fairlee Creek Landing
Almost full
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Fairlee Creek Landing
Sales end soon
Short Attention Span Theatre 2025
Today at 8:00 PM + 7 more
Garfield Center for the Arts at the Prince Theatre
Sales end soon
Short Attention Span Theatre 2025
Today at 8:00 PM + 7 more
Garfield Center for the Arts at the Prince Theatre
"Rhythm-N-Vines"
Sat, Sep 6, 1:00 PM
9155 American Legion Rd
"Rhythm-N-Vines"
Sat, Sep 6, 1:00 PM
9155 American Legion Rd
Almost full
Schooner SULTANA Public Sails 2025-August
Fri, Aug 8, 5:30 PM
Chestertown Marina
Almost full
Schooner SULTANA Public Sails 2025-August
Fri, Aug 8, 5:30 PM
Chestertown Marina
Sales end soon
Bookish Friendship Bracelet Wreathe Crafternoon at the Bookstore!
Sun, Jul 20, 2:00 PM
204 Banjo Ln suite c
Sales end soon
Bookish Friendship Bracelet Wreathe Crafternoon at the Bookstore!
Sun, Jul 20, 2:00 PM
204 Banjo Ln suite c
Lobster Boil
Today at 2:00 PM
6154 Main St
Lobster Boil
Today at 2:00 PM
6154 Main St
Sales end soon
U-Pick & Picnic at Singletree Farm and Florals
Sun, Jul 20, 8:00 AM + 47 more
Singletree Farm and Florals
Sales end soon
U-Pick & Picnic at Singletree Farm and Florals
Sun, Jul 20, 8:00 AM + 47 more
Singletree Farm and Florals
Mojo Car Show 2025
Sun, Aug 3, 12:00 PM
Cunion Field
Mojo Car Show 2025
Sun, Aug 3, 12:00 PM
Cunion Field
Sales end soon
Summer Concert: Tramps Like Us - The #1 Bruce Springsteen Tribute Band
Today at 7:00 PM
237 Bohemia Manor Farm Ln
Sales end soon
Summer Concert: Tramps Like Us - The #1 Bruce Springsteen Tribute Band
Today at 7:00 PM
237 Bohemia Manor Farm Ln
Flow and Glow: A Waterside Self-Care Day
Sat, Aug 23, 10:00 AM
Flying Point Park
Flow and Glow: A Waterside Self-Care Day
Sat, Aug 23, 10:00 AM
Flying Point Park
Eastern's Bayside Festival
Sat, Aug 16, 1:00 PM
2330 Seneca Road
Eastern's Bayside Festival
Sat, Aug 16, 1:00 PM
2330 Seneca Road
Women In The Trenches Ladies Conference
Sat, Aug 9, 10:00 AM
Hyatt Place Kent Narrows & Marina
Women In The Trenches Ladies Conference
Sat, Aug 9, 10:00 AM
Hyatt Place Kent Narrows & Marina
Sunflower Porch Board TCHS 85
Thu, Aug 7, 6:00 PM
Pooles Island Brewing Company
Sunflower Porch Board TCHS 85
Thu, Aug 7, 6:00 PM
Pooles Island Brewing Company
Candle Workshop at Harvest Ridge
Sun, Aug 17, 1:00 PM
Harvest Ridge Winery
Candle Workshop at Harvest Ridge
Sun, Aug 17, 1:00 PM
Harvest Ridge Winery
Eastern Shore Charity Golf Tournament
Thu, Oct 2, 9:00 AM
Queenstown Harbor Golf
Eastern Shore Charity Golf Tournament
Thu, Oct 2, 9:00 AM
Queenstown Harbor Golf

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:

Maryland Commodity Classic 2025

Washington College Field Hockey Summer Clinic

Grape Expectations: A Playful Plates Party -Brampton 1860, Flavors of Spain

Lotus Paddle 2 - 2025 - Sultana Education Foundation

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

immigration protest

Which events are coming up?

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

Summer Concert: Tramps Like Us - The #1 Bruce Springsteen Tribute Band

Short Attention Span Theatre 2025

U-Pick & Picnic at Singletree Farm and Florals