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Community Events and Things to do in Chestertown, MD

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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
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
Sales end soon
THE BLACK MALL SUNDAY! - (Bmore's Love Market/SUNDAY FUN DAY)
Sunday at 1:00 PM
Charles North · The Black Mall
Sales end soon
THE BLACK MALL SUNDAY! - (Bmore's Love Market/SUNDAY FUN DAY)
Sunday at 1:00 PM
Charles North · The Black Mall
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
Sales end soon
One Block Wonder
Fri, Aug 21, 10:00 AM
Denton · Fiber Arts Center Eastern Shore (FACES)
Sales end soon
One Block Wonder
Fri, Aug 21, 10:00 AM
Denton · Fiber Arts Center Eastern Shore (FACES)
The Good Girlfriends Upscale Yardsale
Sun, Sep 27, 11:00 AM
Jones Falls Area · KSM Candle Co
The Good Girlfriends Upscale Yardsale
Sun, Sep 27, 11:00 AM
Jones Falls Area · KSM Candle Co
Sales end soon
GHANA FESTIVAL 2027
Saturday at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Sales end soon
GHANA FESTIVAL 2027
Saturday at 1:00 PM
Crownsville · Anne Arundel County Fairgrounds
Flea Market and School Supply Giveaway
Sat, Aug 22, 9:00 AM
Stonewood-Pentwood-Winston · 4499 Loch Raven Blvd
Flea Market and School Supply Giveaway
Sat, Aug 22, 9:00 AM
Stonewood-Pentwood-Winston · 4499 Loch Raven Blvd
Sales end soon
CampHer 2026: The Ultimate Picnic in the Park
Saturday at 12:00 PM
Delaware · G & R Recreation Campground
Sales end soon
CampHer 2026: The Ultimate Picnic in the Park
Saturday at 12:00 PM
Delaware · G & R Recreation Campground
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
For the Love of Jouvert 2026
Sat, Sep 12, 6:00 AM
Reservoir Hill · Druid Hill Park Lake Pool
For the Love of Jouvert 2026
Sat, Sep 12, 6:00 AM
Reservoir Hill · Druid Hill Park Lake Pool
Almost full
Vendor & Partner Registration: Autism Community Fall Fest & Resource Fair
Sat, Sep 19, 12:00 PM
Overlea · 8363 Town Center Ct
Almost full
Vendor & Partner Registration: Autism Community Fall Fest & Resource Fair
Sat, Sep 19, 12:00 PM
Overlea · 8363 Town Center Ct
Autism Community Fall Fest & Sensory Resource Fair
Sat, Sep 19, 12:00 PM
Overlea · 8363 Town Center Ct
Autism Community Fall Fest & Sensory Resource Fair
Sat, Sep 19, 12:00 PM
Overlea · 8363 Town Center Ct
Milford Mill UMC Fall Flea Market 2026
Sat, Sep 19, 9:00 AM
Lochearn · 915 Milford Mill Rd
Milford Mill UMC Fall Flea Market 2026
Sat, Sep 19, 9:00 AM
Lochearn · 915 Milford Mill Rd
Sales end soon
Island Fest
Saturday at 4:00 PM
Maryland · Hamlet Clubhouse Pavilion
Sales end soon
Island Fest
Saturday at 4:00 PM
Maryland · Hamlet Clubhouse Pavilion
Sales end soon
Bello Machre Open House & Community Resources Fair
Saturday at 10:00 AM
Glen Burnie · 7765 Freetown Rd
Sales end soon
Bello Machre Open House & Community Resources Fair
Saturday at 10:00 AM
Glen Burnie · 7765 Freetown Rd
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
Baltimore CONNECT & The ICTR Community Autumn Resource Fair 2026
Sat, Aug 29, 12:00 PM
University Of Maryland · Lexington Market
Baltimore CONNECT & The ICTR Community Autumn Resource Fair 2026
Sat, Aug 29, 12:00 PM
University Of Maryland · Lexington Market
Selling fast
Mount Zion Baptist Church Community Day FREE
Sun, Sep 20, 10:30 AM
Loch Raven · 2000 E Belvedere Ave Baltimore, MD 21239
Selling fast
Mount Zion Baptist Church Community Day FREE
Sun, Sep 20, 10:30 AM
Loch Raven · 2000 E Belvedere Ave Baltimore, MD 21239
DPW Shred Event
Sat, Aug 22, 8:00 AM
Brooklyn Park · Coppin State University - General Parking Lot C
DPW Shred Event
Sat, Aug 22, 8:00 AM
Brooklyn Park · Coppin State University - General Parking Lot C

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:

End of Summer Kickoff at Town Square

The 3rd Annual Children's Veg Fest

THE BLACK MALL SUNDAY! - (Bmore's Love Market/SUNDAY FUN DAY)

Fairgrounds Takeover PT.2

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:

Bello Machre Open House & Community Resources Fair

CampHer 2026: The Ultimate Picnic in the Park

GHANA FESTIVAL 2027