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Community Events and Things to do in Chestertown, MD

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Shoes at the Door
Thu, Jul 9, 1:00 PM + 10 more
Baltimore · Station North Arts Disctrict
Shoes at the Door
Thu, Jul 9, 1:00 PM + 10 more
Baltimore · Station North Arts Disctrict
Monthly Black Artist Fair
Tue, Jun 16, 6:00 PM + 3 more
Baltimore · Shake & Bake Family Fun Center
Monthly Black Artist Fair
Tue, Jun 16, 6:00 PM + 3 more
Baltimore · Shake & Bake Family Fun Center
Fairgrounds Takeover PT.2
Sat, Aug 29, 11:00 AM
Harrington · Delaware State Fairgrounds
Fairgrounds Takeover PT.2
Sat, Aug 29, 11:00 AM
Harrington · Delaware State Fairgrounds
Milford Mill United Methodist Church Summer Flea Market
Sat, Jun 20, 9:00 AM
Pikesville · Old Milford Mill Road
Milford Mill United Methodist Church Summer Flea Market
Sat, Jun 20, 9:00 AM
Pikesville · Old Milford Mill Road
DMV AFRICAN CARIBBEAN CULTURAL FASHION HERITAGE 5.0 & AFRICA FASHION WEEK
Sat, May 1, 3:00 PM
Gambrills · 1316 Main Chapel Way
DMV AFRICAN CARIBBEAN CULTURAL FASHION HERITAGE 5.0 & AFRICA FASHION WEEK
Sat, May 1, 3:00 PM
Gambrills · 1316 Main Chapel Way
7th Annual World Ebony Network (WEN) Global Chiefs for Change Segment
Sat, Jun 13, 11:00 AM
Jessup · Holiday Inn Columbia East-Jessup by IHG
7th Annual World Ebony Network (WEN) Global Chiefs for Change Segment
Sat, Jun 13, 11:00 AM
Jessup · Holiday Inn Columbia East-Jessup by IHG
6th Annual Back to School Bash Community Giveaway | The Empress Team
Sat, Aug 8, 3:00 PM
Randallstown · 4000 Offutt Rd
6th Annual Back to School Bash Community Giveaway | The Empress Team
Sat, Aug 8, 3:00 PM
Randallstown · 4000 Offutt Rd
Just added
Pride Full Moon Sound Celebration
Mon, Jun 29, 7:00 PM
New Castle · 201 Delaware St
Just added
Pride Full Moon Sound Celebration
Mon, Jun 29, 7:00 PM
New Castle · 201 Delaware St
Almost full
Parish Picnic at the Blue Rocks
Sat, Jun 27, 5:30 PM
Wilmington · Wilmington Blue Rocks
Almost full
Parish Picnic at the Blue Rocks
Sat, Jun 27, 5:30 PM
Wilmington · Wilmington Blue Rocks
Going fast
Delaware Black Wall Street Festival
Sat, Jun 20, 3:00 PM
Wilmington · 2409 Lancaster Ave
Going fast
Delaware Black Wall Street Festival
Sat, Jun 20, 3:00 PM
Wilmington · 2409 Lancaster Ave
Stitched in History: Quilts, Codes & Conversation
Sat, Aug 1, 12:30 PM
Columbia · Harriet Tubman Cultural Center
Stitched in History: Quilts, Codes & Conversation
Sat, Aug 1, 12:30 PM
Columbia · Harriet Tubman Cultural Center
St. Anthony's Italian Festival: 2026
Sunday at 4:00 PM
Wilmington · St. Anthony of Padua Roman Catholic Church, North Dupont Street, Wilmington, DE, USA
St. Anthony's Italian Festival: 2026
Sunday at 4:00 PM
Wilmington · St. Anthony of Padua Roman Catholic Church, North Dupont Street, Wilmington, DE, USA
Hotter Than July
Sun, Jul 12, 2:00 PM
Wilmington · Docklands Riverfront
Hotter Than July
Sun, Jul 12, 2:00 PM
Wilmington · Docklands Riverfront
Caribbean Passion
Sat, Jun 20, 8:00 PM
Wilmington · Docklands Riverfront
Caribbean Passion
Sat, Jun 20, 8:00 PM
Wilmington · Docklands Riverfront
Nigerian Independence Day Festival
Sun, Oct 11, 1:00 PM
Lanham · 9800 Good Luck Rd
Nigerian Independence Day Festival
Sun, Oct 11, 1:00 PM
Lanham · 9800 Good Luck Rd
Sales end soon
Marlboro Day
Saturday at 10:00 AM
Upper Marlboro · Governor Oden Bowie Drive
Sales end soon
Marlboro Day
Saturday at 10:00 AM
Upper Marlboro · Governor Oden Bowie Drive
The Pit, The Porch & The Table: A Juneteenth Celebration
Fri, Jun 19, 2:00 PM
Upper Marlboro · Wellspring Manor & Spa
The Pit, The Porch & The Table: A Juneteenth Celebration
Fri, Jun 19, 2:00 PM
Upper Marlboro · Wellspring Manor & Spa
The Author Space Book & Art Festival
Sat, Nov 14, 10:00 AM
Upper Marlboro · The Show Place Arena
The Author Space Book & Art Festival
Sat, Nov 14, 10:00 AM
Upper Marlboro · The Show Place Arena
FESTIVAL OF INDIA
Sat, Sep 19, 12:00 PM
West Friendship · Howard County Fairgrounds
FESTIVAL OF INDIA
Sat, Sep 19, 12:00 PM
West Friendship · Howard County Fairgrounds
CAACO Juneteenth Celebration
Sat, Jun 20, 12:00 PM
Cheverly · 6401 Forest Rd
CAACO Juneteenth Celebration
Sat, Jun 20, 12:00 PM
Cheverly · 6401 Forest Rd

Trends in Chestertown

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Explore more trends

Frequently asked questions about Chestertown

What are the best festival events to attend?

According to Eventbrite, the best festival events are:

Shoes at the Door

Fairgrounds Takeover PT.2

Milford Mill United Methodist Church Summer Flea Market

DMV AFRICAN CARIBBEAN CULTURAL FASHION HERITAGE 5.0 & AFRICA FASHION WEEK

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:

St. Anthony's Italian Festival: 2026

7th Annual World Ebony Network (WEN) Global Chiefs for Change Segment

Monthly Black Artist Fair