May 2019

The event is designed to allow Dorchester County residents to celebrate all we have to offer related to food and our heritage. Each year we gather local ingredients from purveyors in the County: Fresh seafood, meat, poultry, grains, fruit and vegetables, all grown and raised in the region. We then give those ingredients to local chefs to use to produce a dish to serve attendees at the event. Celebrate the freshness of Dorchester-produced foods, the artistry of our local chefs, the excellence of our County's businesses, and the camaraderie of our friends and neighbors! To be a vendor or tickets call the chamber (410) 228-3575

Fun Dog Show

May 9th 2020

"Fun dog Show" in Governor's Hall at Sailwinds Park along the choptank river. This event has grown into a local tradition. Registration begins at 9Am and begins with a blessing of all dogs and a parade of all dogs and their owners at 10 am. A raffle features gift certificates from much local business; the event is free to the public. For more information or to be a sponsor Call Christ Church 410-228-3161

The sooner you get started, the more money you can raise. The more money you raise, the more incentive prizes you earn. So register early and get ready for a great fundraising season.

Charcoaled Comedy at Governors Hall at Sailwinds Park

Looking for non-stop laughter? Jokes after jokes? Mark Saturday May 16th 8pm on your calendar and join all your friends at Governors Hall at Sailwinds Park in Cambridge Maryland! Charcoaled Comedy returns to the shore with 4 hilarious Maryland comedians! Enjoy the comedy stylings of Mike Moran and Robin Hazel with your host, Big Timing Comedy's very own Stefan Subotich! Prank Call Extraordinaire R.J. Jackson will close the night out and might even call your unsuspecting friends who couldn't make the show! Doors open at 6pm for those early birds looking for dinner and drinks at the Osprey Nest nestled in Governors Hall. Tickets are only $10 and can be purchased right here online or charge by phone 443-477-6276 Wednesday-Saturday between 1pm-6pm. Make sure this date and time is on your calendar because you don't want to miss the punchlines Saturday May 16th 8pm-10pm.

Maryland Eastern Shore Ruff Ryders

Maryland Eastern Shore Ruff Ryders

May 23rd, 2020 at 1 pm

Maryland eastern shore Ruff Ryders yard and night party, starting at 1pm with food, games, moon bounces, mechanical bull, bike show, 50/50, and music

June 2020

Happy Anniversary week

June 3rd - 6th

6 Happy Anniversary week at the Osprey's Nest/ Governors Hall at Sailwinds Park
call for more information 410-225-6283 or 443-477-6276

July 2020


July 3rd-4tth

Music, games, moon bounces for the kids, food, yard sale, and fireworks
call 410-225-6283 or 443-477-6276

August 2020

Seafood Festival

August 8th 2020

it's the Annual Rescues Fire Company Seafood Festival at Governors Hall at Sailwinds Park, Saturday August 8 1pm-6pm. Gates open at one. Musical entertainment, enjoy steamed Crabs, Crab Soup, Fries Fish, Fried Clams, BBQ Chicken, Ranch Fries and so much more. The event is rain or shine Call 410-228-1211

Rude Boy Motorcycle Dance Party

August 15th 2020

September 2020

Crabtober Fest

September 26 2020

Crabtoberfest is our way of giving Dorchester and surrounding areas a small taste of German food, music, and fun while raising funds to support activities related to the student exchange. For more information contact the Dorchester Chamber of Commerce at 410-228-3575

October 2020

Cedar Meadows Rod and Gun Club Crab festival

October 3rd 2020 at 12noon-7pm

Cedar Meadows Rod and Gun Club Crab festival - October 3rd 2020 12noon-7pm. enjoy great seafood, drinks, Fun and music.
Call for tickets: (410) 228-9653

Sailwinds "Yard Sale"

October 10th 2020 at 7am-12pm

For tables call 410-225-6283 or 443-477-6276

Haunted Forest at Sailwinds Park

October 25th - 31st17th

Saturday October 31 it's the Monster Mash Bash and Costume Party
FREE for ages 2 and up.

Kids come dress in you favorite costume to win prizes, enjoy three different moon bounces, and dance to some of your favorite BOOtacular music and free candy!

call 410-225-6283 or 443-477-6276




Call 410-225-6283 or 443-477-6276

Harriett House fundraiser

November 7th 2020 at 9am-12pm

Harriett House fundraiser 9am-12pm, Breakfast included with tickets call 443-786-1843 for more information on Harriett House and the fundraiser