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Events and Things to do in Cheswold, DE

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2026 SHAPE Delaware Convention
Tue, Sep 15, 7:30 AM
Milford · Milford Senior High School
2026 SHAPE Delaware Convention
Tue, Sep 15, 7:30 AM
Milford · Milford Senior High School
Sales end soon
Bohemia Manor Winery: Tour and Taste
Tomorrow at 12:00 PM + 131 more
Chesapeake City · 237 Bohemia Manor Farm Ln
Sales end soon
Bohemia Manor Winery: Tour and Taste
Tomorrow at 12:00 PM + 131 more
Chesapeake City · 237 Bohemia Manor Farm Ln
Held: Retreat for Birthworkers
Fri, Jul 10, 4:00 PM
Houston · G & R Recreation Campground
Held: Retreat for Birthworkers
Fri, Jul 10, 4:00 PM
Houston · G & R Recreation Campground
2nd Annual B/H Milford Reunion Community Day
Sat, Aug 1, 12:00 PM
Milford · Benjamin Banneker Elem School
2nd Annual B/H Milford Reunion Community Day
Sat, Aug 1, 12:00 PM
Milford · Benjamin Banneker Elem School
Just added
On Farm Dinner
Thu, Jun 18, 6:30 PM
Chestertown · 2517 McGinnes Rd
Just added
On Farm Dinner
Thu, Jun 18, 6:30 PM
Chestertown · 2517 McGinnes Rd
The Weaver’s Web: Weaving in the Round
Sat, Jun 6, 3:00 PM
Milford · 206 N Walnut St
The Weaver’s Web: Weaving in the Round
Sat, Jun 6, 3:00 PM
Milford · 206 N Walnut St
Gong Bath
Sat, May 30, 7:00 PM
Bear · Whispering Oak Mansion
Gong Bath
Sat, May 30, 7:00 PM
Bear · Whispering Oak Mansion
Almost full
Turtle Paddle - 2026 - Sultana Education Foundation
Sat, Jun 13, 10:00 AM
Queen Anne · Tuckahoe State Park Boat Ramp
Almost full
Turtle Paddle - 2026 - Sultana Education Foundation
Sat, Jun 13, 10:00 AM
Queen Anne · Tuckahoe State Park Boat Ramp
Danny Paisley and the Southern Grass
Sat, Jun 27, 7:00 PM
Chestertown · Chestertown Volunteer Fire Co
Danny Paisley and the Southern Grass
Sat, Jun 27, 7:00 PM
Chestertown · Chestertown Volunteer Fire Co
Father's Day Car Show
Sun, Jun 21, 8:00 AM
Bear · Christ the Cornerstone Church
Father's Day Car Show
Sun, Jun 21, 8:00 AM
Bear · Christ the Cornerstone Church
Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation
Sun, Oct 25, 10:00 AM
Chestertown · Rileys Mill Landing
Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation
Sun, Oct 25, 10:00 AM
Chestertown · Rileys Mill Landing
Ethics in the Arena
Fri, Jun 12, 1:00 PM
Lincoln · Courageous Hearts
Ethics in the Arena
Fri, Jun 12, 1:00 PM
Lincoln · Courageous Hearts
Womens Soul Circle: Self Love Series
Thu, May 21, 6:00 PM
Lincoln · Courageous Hearts
Womens Soul Circle: Self Love Series
Thu, May 21, 6:00 PM
Lincoln · Courageous Hearts
Movie & Arts Night: Drop-Off Studio Experience for Kids in Chestertown
Fri, May 22, 6:00 PM + 2 more
Chestertown · Artist Michael Bell Studio & Workshops
Movie & Arts Night: Drop-Off Studio Experience for Kids in Chestertown
Fri, May 22, 6:00 PM + 2 more
Chestertown · Artist Michael Bell Studio & Workshops
Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation
Sat, Sep 19, 10:00 AM
Chestertown · Stillpond Creek
Oysters and Indians Public Paddle - 2026 - Sultana Education Foundation
Sat, Sep 19, 10:00 AM
Chestertown · Stillpond Creek
Schooner SULTANA Public Sails 2026-May
Sat, May 23, 4:30 PM
Chestertown · Chestertown Marina
Schooner SULTANA Public Sails 2026-May
Sat, May 23, 4:30 PM
Chestertown · Chestertown Marina
Going fast
Breathe Easy Fridays (youth mini camps on the farm)
Fri, Jul 10, 9:30 AM
Lincoln · Courageous Hearts
Going fast
Breathe Easy Fridays (youth mini camps on the farm)
Fri, Jul 10, 9:30 AM
Lincoln · Courageous Hearts
Womens Wellnes Retreat on the Farm
Sat, Jun 6, 9:00 AM
Lincoln · Courageous Hearts
Womens Wellnes Retreat on the Farm
Sat, Jun 6, 9:00 AM
Lincoln · Courageous Hearts
Going fast
Introduction to Spinning Wheels
Wed, Jun 10, 1:00 PM
Denton · Fiber Arts Center Eastern Shore (FACES)
Going fast
Introduction to Spinning Wheels
Wed, Jun 10, 1:00 PM
Denton · Fiber Arts Center Eastern Shore (FACES)
Grape Expectations: Brampton 1860 “Mexico Reimagined”
Thu, May 28, 6:00 PM
Chestertown · 25227 Chestertown Rd
Grape Expectations: Brampton 1860 “Mexico Reimagined”
Thu, May 28, 6:00 PM
Chestertown · 25227 Chestertown Rd

7 of 500

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Frequently asked questions about Cheswold

What are the best events to attend?

According to Eventbrite, the best events are:

2026 SHAPE Delaware Convention

Held: Retreat for Birthworkers

2nd Annual B/H Milford Reunion Community Day

Which events are currently trending in Cheswold?

The trending searches this month in Cheswold are:

Which events are coming up?

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

Bohemia Manor Winery: Tour and Taste

Womens Soul Circle: Self Love Series

Movie & Arts Night: Drop-Off Studio Experience for Kids in Chestertown

Schooner SULTANA Public Sails 2026-May

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