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Events in Chestertown, MD

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Sales end soon
BBQ & BREWS | Get SAUCED at Piney Grove
Tomorrow at 12:00 PM
Piney Grove
Sales end soon
BBQ & BREWS | Get SAUCED at Piney Grove
Tomorrow at 12:00 PM
Piney Grove
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
That's the Spirit
Sat, Sep 13, 4:30 PM
Watershed Alley
That's the Spirit
Sat, Sep 13, 4:30 PM
Watershed Alley
"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
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Fairlee Creek Landing
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Fairlee Creek Landing
Sultana's Downrigging-Festival Village Passes-2025
Fri, Oct 31, 3:00 PM
Chestertown Marina
Sultana's Downrigging-Festival Village Passes-2025
Fri, Oct 31, 3:00 PM
Chestertown Marina
Grape Expectations: A Playful Plates Party at Brampton 1860, Gourmet Picnic
Thu, Aug 21, 6:00 PM
25227 Chestertown Rd
Grape Expectations: A Playful Plates Party at Brampton 1860, Gourmet Picnic
Thu, Aug 21, 6:00 PM
25227 Chestertown Rd
Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm
Fri, Oct 31, 2:30 PM
Chestertown Marina
Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm
Fri, Oct 31, 2:30 PM
Chestertown Marina
Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation
Sun, Oct 26, 10:00 AM
Rileys Mill Landing
Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation
Sun, Oct 26, 10:00 AM
Rileys Mill Landing
Schooner SULTANA Public Sails 2025-August
Fri, Aug 8, 5:30 PM
Chestertown Marina
Schooner SULTANA Public Sails 2025-August
Fri, Aug 8, 5:30 PM
Chestertown Marina
Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm
Sat, Nov 1, 2:30 PM
Chestertown Marina
Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm
Sat, Nov 1, 2:30 PM
Chestertown Marina
Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm
Sun, Nov 2, 1:00 PM
Chestertown Marina
Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm
Sun, Nov 2, 1:00 PM
Chestertown Marina
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
CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event
Sat, Aug 23, 1:00 PM
Island View Waterfront- 2542 Island View Rd
CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event
Sat, Aug 23, 1:00 PM
Island View Waterfront- 2542 Island View Rd
Sales end soon
Mojo Car Show 2025
Sunday at 12:00 PM
Cunion Field
Sales end soon
Mojo Car Show 2025
Sunday at 12:00 PM
Cunion Field
U-Pick & Picnic at Singletree Farm and Florals
Tomorrow at 8:00 AM + 41 more
Singletree Farm and Florals
U-Pick & Picnic at Singletree Farm and Florals
Tomorrow at 8:00 AM + 41 more
Singletree Farm and Florals
Ink & Indie - Book Signing Event - 2025 - Saturday | Main Signing Event
Sat, Oct 4, 10:00 AM
The Bank
Ink & Indie - Book Signing Event - 2025 - Saturday | Main Signing Event
Sat, Oct 4, 10:00 AM
The Bank
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
Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm
Sat, Nov 1, 10:30 AM
Chestertown Marina
Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm
Sat, Nov 1, 10:30 AM
Chestertown Marina
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

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:

Lotus Paddle 2 - 2025 - Sultana Education Foundation

That's the Spirit

"Rhythm-N-Vines"

Fairlee Creek-2025- Public Paddle - Sultana Education Foundation

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

chestertown car show

minary's dream alliance inc

events happening today near me

Which events are coming up?

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

U-Pick & Picnic at Singletree Farm and Florals

BBQ & BREWS | Get SAUCED at Piney Grove

Mojo Car Show 2025

Schooner SULTANA Public Sails 2025-August