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Community Events and Things to do in Chestertown, MD

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Sales end soon
Nilachal Anniversary Market
Saturday at 10:00 AM
Maryland · 279 Joe Meltz Rd
Sales end soon
Nilachal Anniversary Market
Saturday at 10:00 AM
Maryland · 279 Joe Meltz Rd
End of Summer Kickoff at Town Square
Sat, Aug 22, 10:00 AM
Overlea · 9708 Belair Rd
End of Summer Kickoff at Town Square
Sat, Aug 22, 10:00 AM
Overlea · 9708 Belair Rd
Almost full
Biddy Presents : Biddy on The Water : Rodeo Theme at Canton Waterfront Park
Sun, Jul 5, 12:00 PM
Canton · Canton Waterfront Park
Almost full
Biddy Presents : Biddy on The Water : Rodeo Theme at Canton Waterfront Park
Sun, Jul 5, 12:00 PM
Canton · Canton Waterfront Park
Sales end soon
Blooming Inclusiveness: 2nd Annual Sunflower Planting
Friday at 10:00 AM
Bel Air North · Edgeley Grove Park
Sales end soon
Blooming Inclusiveness: 2nd Annual Sunflower Planting
Friday at 10:00 AM
Bel Air North · Edgeley Grove Park
Going fast
Voices of History Street Fair
Saturday at 11:00 AM
Oliver · The National Great Blacks In Wax Museum
Going fast
Voices of History Street Fair
Saturday at 11:00 AM
Oliver · The National Great Blacks In Wax Museum
Black Butterfly Farm Community Day
Sat, Jul 25, 10:00 AM
Curtis Bay · Farm Alliance Black Butterfly Teaching Farm
Black Butterfly Farm Community Day
Sat, Jul 25, 10:00 AM
Curtis Bay · Farm Alliance Black Butterfly Teaching Farm
Just added
One Block Wonder
Fri, Aug 21, 10:00 AM
Denton · Fiber Arts Center Eastern Shore (FACES)
Just added
One Block Wonder
Fri, Aug 21, 10:00 AM
Denton · Fiber Arts Center Eastern Shore (FACES)
Carnival Invasion 4
Sat, Jul 11, 10:00 PM
East Baltimore Midway · 2308 Harford Rd
Carnival Invasion 4
Sat, Jul 11, 10:00 PM
East Baltimore Midway · 2308 Harford Rd
ARMYRANG Baltimore Vendor Market
Tue, Aug 11, 11:00 AM
University Of Maryland · Lexington Market
ARMYRANG Baltimore Vendor Market
Tue, Aug 11, 11:00 AM
University Of Maryland · Lexington Market
Almost full
Ditch Day Beach Club
Friday at 12:00 PM
Druid Hill Park · 1876 Mansion House Dr
Almost full
Ditch Day Beach Club
Friday at 12:00 PM
Druid Hill Park · 1876 Mansion House Dr
Going fast
Crazee Lymerz - One Day Bus Excursion- Delaware Caribbean Carnival 2026
Sat, Aug 15, 6:00 AM
Schoolview · 410 Legislative Ave
Going fast
Crazee Lymerz - One Day Bus Excursion- Delaware Caribbean Carnival 2026
Sat, Aug 15, 6:00 AM
Schoolview · 410 Legislative Ave
The 3rd Annual Children's Veg Fest
Sat, Aug 29, 11:00 AM
Ednor Gardens-Lakeside · The Weinberg Y in Waverly
The 3rd Annual Children's Veg Fest
Sat, Aug 29, 11:00 AM
Ednor Gardens-Lakeside · The Weinberg Y in Waverly
Runaway Jouvert
Fri, Jul 10, 3:00 PM
Druid Hill Park · Druid Hill Park
Runaway Jouvert
Fri, Jul 10, 3:00 PM
Druid Hill Park · Druid Hill Park
Troublems Jouvert (Baltimore Edition)
Sat, Jul 11, 12:00 PM
Reservoir Hill · Druid Hill Park
Troublems Jouvert (Baltimore Edition)
Sat, Jul 11, 12:00 PM
Reservoir Hill · Druid Hill Park
Jerry Day
Sun, Aug 2, 3:00 PM
Medfield · Union Craft Brewing
Jerry Day
Sun, Aug 2, 3:00 PM
Medfield · Union Craft Brewing
2026 Baltimore Crown Awards: Celebrating 20 Years of The Baltimore Scene
Sun, Dec 6, 7:00 PM
Downtown · 316 Guilford Ave
2026 Baltimore Crown Awards: Celebrating 20 Years of The Baltimore Scene
Sun, Dec 6, 7:00 PM
Downtown · 316 Guilford Ave
Monthly Black Artist Fair
Tue, Jul 21, 6:00 PM + 2 more
Upton · Shake & Bake Family Fun Center
Monthly Black Artist Fair
Tue, Jul 21, 6:00 PM + 2 more
Upton · Shake & Bake Family Fun Center
Fairgrounds Takeover PT.2
Sat, Aug 29, 11:00 AM
Delaware · Delaware State Fairgrounds
Fairgrounds Takeover PT.2
Sat, Aug 29, 11:00 AM
Delaware · Delaware State Fairgrounds
CampHer 2026
Sat, Aug 15, 12:00 PM
Delaware · G & R Recreation Campground
CampHer 2026
Sat, Aug 15, 12:00 PM
Delaware · G & R Recreation Campground
DMV AFRICAN CARIBBEAN CULTURAL FASHION HERITAGE 5.0 & AFRICA FASHION WEEK
Sat, May 1, 3:00 PM
Odenton · 1316 Main Chapel Way
DMV AFRICAN CARIBBEAN CULTURAL FASHION HERITAGE 5.0 & AFRICA FASHION WEEK
Sat, May 1, 3:00 PM
Odenton · 1316 Main Chapel Way

Trends in Chestertown

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Frequently asked questions about Chestertown

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

End of Summer Kickoff at Town Square

Biddy Presents : Biddy on The Water : Rodeo Theme at Canton Waterfront Park

Black Butterfly Farm Community Day

One Block Wonder

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

events happening today near me

yard sales and estate sale

Which festival events are coming up?

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

Blooming Inclusiveness: 2nd Annual Sunflower Planting

Ditch Day Beach Club

Nilachal Anniversary Market

Voices of History Street Fair