Events in Chestertown, MD

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

"Rhythm-N-Vines"
Sat, Sep 6, 1:00 PM
Heron Point · 9155 American Legion Rd
"Rhythm-N-Vines"
Sat, Sep 6, 1:00 PM
Heron Point · 9155 American Legion Rd
2025 Chestertown Jazz Festival
Sat, Sep 6, 12:00 PM
Heron Point · Wilmer Park
2025 Chestertown Jazz Festival
Sat, Sep 6, 12:00 PM
Heron Point · Wilmer Park
That's the Spirit
Sat, Sep 13, 4:30 PM
Heron Point · Watershed Alley
That's the Spirit
Sat, Sep 13, 4:30 PM
Heron Point · Watershed Alley
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Maryland · Fairlee Creek Landing
Fairlee Creek-2025- Public Paddle - Sultana Education Foundation
Sat, Sep 13, 9:00 AM
Maryland · Fairlee Creek Landing
Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm
Sat, Nov 1, 2:30 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm
Sat, Nov 1, 2:30 PM
Heron Point · Chestertown Marina
Sultana's Downrigging-Festival Village Passes-2025
Fri, Oct 31, 3:00 PM
Heron Point · Chestertown Marina
Sultana's Downrigging-Festival Village Passes-2025
Fri, Oct 31, 3:00 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm
Fri, Oct 31, 2:30 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm
Fri, Oct 31, 2:30 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm
Sun, Nov 2, 1:00 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm
Sun, Nov 2, 1:00 PM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm
Sat, Nov 1, 10:30 AM
Heron Point · Chestertown Marina
Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm
Sat, Nov 1, 10:30 AM
Heron Point · Chestertown Marina
Nearly full
Queen Anne's County Historical Society - Farm to Table Dinner
Thu, Sep 11, 5:00 PM
Maryland · Mason Farms Produce
Nearly full
Queen Anne's County Historical Society - Farm to Table Dinner
Thu, Sep 11, 5:00 PM
Maryland · Mason Farms Produce
2nd Annual Sass-a-Palooza
Fri, Sep 26, 3:00 PM
Maryland · 150 Skipjack Rd
2nd Annual Sass-a-Palooza
Fri, Sep 26, 3:00 PM
Maryland · 150 Skipjack Rd
Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation
Sun, Oct 26, 10:00 AM
Maryland · Rileys Mill Landing
Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation
Sun, Oct 26, 10:00 AM
Maryland · Rileys Mill Landing
CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event
Today at 1:00 PM
Saint Helena · Island View Waterfront- 2542 Island View Rd
CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event
Today at 1:00 PM
Saint Helena · Island View Waterfront- 2542 Island View Rd
Just added!
Grape Expectations: A Playful Plates Party at Brampton 1860, Autumn Harvest
Thu, Sep 18, 6:00 PM
Maryland · 25227 Chestertown Rd
Just added!
Grape Expectations: A Playful Plates Party at Brampton 1860, Autumn Harvest
Thu, Sep 18, 6:00 PM
Maryland · 25227 Chestertown Rd
HCAC Presents: MixxedFit with Cardio ViXens
Sat, Sep 6, 10:00 AM
Edgewood · Edgewood Middle School
HCAC Presents: MixxedFit with Cardio ViXens
Sat, Sep 6, 10:00 AM
Edgewood · Edgewood Middle School
Schooner SULTANA Public Sails 2025-September 13 & 20
Sat, Sep 13, 11:00 AM + 3 more
Heron Point · Chestertown Marina
Schooner SULTANA Public Sails 2025-September 13 & 20
Sat, Sep 13, 11:00 AM + 3 more
Heron Point · Chestertown Marina
Back to school paint party (Middle School Grades)
Sat, Aug 30, 3:00 PM
Millington · Millington
Back to school paint party (Middle School Grades)
Sat, Aug 30, 3:00 PM
Millington · Millington
Back to school paint party (High School Grades)
Sat, Aug 30, 6:00 PM
Millington · 350 Cypress St
Back to school paint party (High School Grades)
Sat, Aug 30, 6:00 PM
Millington · 350 Cypress St
Back to school paint party (Elementary Grades)
Sat, Aug 30, 12:00 PM
Millington · 350 Cypress St
Back to school paint party (Elementary Grades)
Sat, Aug 30, 12:00 PM
Millington · 350 Cypress St

Trends in Chestertown

Explore more trends

Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

"Rhythm-N-Vines"

2025 Chestertown Jazz Festival

That's the Spirit

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

free back to school supply giveaway registration

craft fair

Which events are coming up?

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

CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event

Back to school paint party (Elementary Grades)

Back to school paint party (Middle School Grades)

Back to school paint party (High School Grades)

"Rhythm-N-Vines"

"Rhythm-N-Vines"

2025 Chestertown Jazz Festival

2025 Chestertown Jazz Festival

That's the Spirit

That's the Spirit

Fairlee Creek-2025- Public Paddle - Sultana Education Foundation

Fairlee Creek-2025- Public Paddle - Sultana Education Foundation

Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm

Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm

Sultana's Downrigging-Festival Village Passes-2025

Sultana's Downrigging-Festival Village Passes-2025

Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm

Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm

Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm

Downrigging Weekend Sails--Saturday Morning, Nov. 1, 10:30am-1:00pm

Queen Anne's County Historical Society - Farm to Table Dinner

Queen Anne's County Historical Society - Farm to Table Dinner

2nd Annual Sass-a-Palooza

2nd Annual Sass-a-Palooza

Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation

Waterfowl and Foliage Public Paddle - 2025- Sultana Education Foundation

CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event

CHARMNIC: Summer Bloom Picnic Soirée- 2nd Annual Picnic Style Event

Grape Expectations: A Playful Plates Party at Brampton 1860, Autumn Harvest

Grape Expectations: A Playful Plates Party at Brampton 1860, Autumn Harvest

HCAC Presents: MixxedFit with Cardio ViXens

HCAC Presents: MixxedFit with Cardio ViXens

Schooner SULTANA Public Sails 2025-September 13 & 20

Schooner SULTANA Public Sails 2025-September 13 & 20

Back to school paint party (Middle School Grades)

Back to school paint party (Middle School Grades)

Back to school paint party (High School Grades)

Back to school paint party (High School Grades)

Back to school paint party (Elementary Grades)

Back to school paint party (Elementary Grades)

Things to do around Chestertown

Trends in Chestertown

1. Chestertown car show

2. Minary's dream alliance inc

3. Free back to school supply giveaway registration

4. Craft fair

5. All you can eat crab feast

6. Kent county

7. Free backpacks and school supplies chestertown md

8. Free backpacks and school supplies

9. Chester river catfish tournament

10. Black folk book club fells point

11. Wine festival chestertown

12. Rock hall this weekend