There’s always so much to see and do in Dorchester County, Maryland!
Scroll through our events calendar below to find out more, and submit your own event for consideration!
Calendar of Events
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M Mon
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W Wed
T Thu
F Fri
S Sat
5 events,
Walking Farm Tour at Pop’s Old Place
Walking Farm Tour at Pop’s Old Place
Pop's Old Place offers small Walking Farm Tours (30 to 45 minutes) on the First Sunday of every month starting at 9am. You can walk […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Sunday Gospel Jazz Brunch
Sunday Gospel Jazz Brunch
ArtBar 2.0 hosts an all-you-can-eat Sunday Gospel Jazz Brunch on May 1 from 12 to 4pm (and on most Sundays). Some Sundays feature live entertainment. […]
Groove Theatre Company: “The Wolves”
Groove Theatre Company: “The Wolves”
Groove Theatre Company presents "The Wolves" April 22 to May 1 at the Dorchester Center for the Arts. By Sarah DeLappe; directed by Izzy Clemens. […]
Christ Church Music Series: Solomon Eichner, Piano
Christ Church Music Series: Solomon Eichner, Piano
Christ Episcopal Church presents Solomon Eichner on piano on May 1 at 4pm. A reception follows the concert. The cost is $10 per person. Students […]
1 event,
Richardson Maritime Museum Moving Sale
Richardson Maritime Museum Moving Sale
The Richardson Maritime Museum is moving to their waterfront property. They have lots of items for sale to make room for new exhibits including book […]
0 events,
1 event,
Talk: The Education of Harriet Tubman: How She ‘Came up’ in South Dorchester
Talk: The Education of Harriet Tubman: How She ‘Came up’ in South Dorchester
South Dorchester Folk Museum Presents "The Education of Harriet Tubman: How She ‘Came up’ in South Dorchester" with Phillip Hesser on Wednesday, May 4 at […]
3 events,
Cambridge Farmers Market
Cambridge Farmers Market
Find local produce, meats, cheeses, crafts, and more at the weekly Cambridge Farmers Market. In 2022, the market runs from May 5 through October 27. […]
Richardson Maritime Museum Moving Sale
Richardson Maritime Museum Moving Sale
The Richardson Maritime Museum is moving to their waterfront property. They have lots of items for sale to make room for new exhibits including book […]
Dorchester County Historical Society Spring Recycle Yard Sale
Dorchester County Historical Society Spring Recycle Yard Sale
Shop for a great cause May 5, 6, and 7, 2022 at the spring yard sale of the Heritage Museums & Gardens of Dorchester (home […]
4 events,
Cambridge Ghost Walk
Cambridge Ghost Walk
Take a walk down Haunted High Street in Historic Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange […]
Dorchester County Historical Society Spring Recycle Yard Sale
Dorchester County Historical Society Spring Recycle Yard Sale
Shop for a great cause May 5, 6, and 7, 2022 at the spring yard sale of the Heritage Museums & Gardens of Dorchester (home […]
Richardson Maritime Museum Moving Sale
Richardson Maritime Museum Moving Sale
The Richardson Maritime Museum is moving to their waterfront property. They have lots of items for sale to make room for new exhibits including book […]
CANCELLED – Burning of the Vines at Layton’s Chance Winery
CANCELLED – Burning of the Vines at Layton’s Chance Winery
NOTE: This event has been cancelled because of the weather forecast. It will not be rescheduled. Join Layton's Chance Vineyard & Winery for their 8th […]
7 events,
Six Pillars Century Cycling Event
Cycle the scenic back roads of picturesque Blackwater Wildlife Refuge in Dorchester County, MD as part of the Six Pillars Century Cycling Event on May […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Crawfish Boil & Muskrat Stew Fest
Crawfish Boil & Muskrat Stew Fest
UPDATE: Because of the rainy forecast, the Crawfish Boil & Muskrat Stew Fest is moving INSIDE to Governor's Hall/Sailwinds at 200 Byrn St. in Cambridge. […]
Dorchester County Historical Society Spring Recycle Yard Sale
Dorchester County Historical Society Spring Recycle Yard Sale
Shop for a great cause May 5, 6, and 7, 2022 at the spring yard sale of the Heritage Museums & Gardens of Dorchester (home […]
Great Chesapeake Bay Wellness Race
Great Chesapeake Bay Wellness Race
Join in for the 18th Annual Great Chesapeake Bay Wellness Race - a live race with a virtual component. The race is organized by the […]
Mother’s Day Celebration at Bay Country Shop
Mother’s Day Celebration at Bay Country Shop
In celebration of Mother's Day weekend, Bay Country Shop hosts vendors, give-aways, and gift ideas for your Mom on May 7 from 10am to 5pm. […]
Stephen Philip Harvey Octet at DCA
Stephen Philip Harvey Octet at DCA
The Stephen Philip Harvey Octet (SPH8) performs at the Dorchester Center for the Arts Saturday, May 7 from 7 to 9pm. SPH8 is a collective […]
5 events,
Sunday Gospel Jazz Mother’s Day Brunch
Sunday Gospel Jazz Mother’s Day Brunch
ArtBar 2.0 hosts an all-you-can-eat Sunday Gospel Jazz Mother's Day Brunch on May 8 from 12 to 4pm (and on most Sundays). Some Sundays feature […]
Mother’s Day Brunch at Hyatt Regency Chesapeake Bay
Mother’s Day Brunch at Hyatt Regency Chesapeake Bay
Celebrate Mother’s Day on the Eastern Shore at Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina. The resort will provide an extravagant Mother’s Day […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Crab Run
Cambridge Crab Run
This Mother's Day event on May 8, 2022 offers a half marathon (13.1 miles) immediately followed by a 5k (3.1 miles) run, all from the […]
Mother’s Day Picnic at Layton’s Chance Winery
Mother’s Day Picnic at Layton’s Chance Winery
Treat mom to a picnic on her special day from 12 to 5pm on May 8 at Layton's Chance Vineyard & Winery. Catering from Emily's […]
0 events,
1 event,
Richardson Maritime Museum Moving Sale
Richardson Maritime Museum Moving Sale
The Richardson Maritime Museum is moving to their waterfront property. They have lots of items for sale to make room for new exhibits including book […]
0 events,
1 event,
Cambridge Farmers Market
Cambridge Farmers Market
Find local produce, meats, cheeses, crafts, and more at the weekly Cambridge Farmers Market. In 2022, the market runs from May 5 through October 27. […]
1 event,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
11 events,
2022 Snakehead Mayhem Tournament
2022 Snakehead Mayhem Tournament
The second of five tournaments in the 2022 Snakehead Championship Series, the 2022 Snakehead Mayhem Tournament will be held May 14, 2022. Anglers will be […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Skipjack Sail
Skipjack Sail
Join the Skipjack Nathan of Dorchester – an authentic traditional oyster dredging vessel and Maryland's state boat – for a two-hour cruise on the Choptank […]
Art Reception: Young People’s Show & Concert at DCA
Art Reception: Young People’s Show & Concert at DCA
To celebrate the annual Young People's Show, the Dorchester Center for the Arts hosts a Second Saturday Artists’ Reception and Awards Ceremony on May 14 […]
Art Reception: Hookers, Strippers and Dyers at Main Street Gallery
Art Reception: Hookers, Strippers and Dyers at Main Street Gallery
Main Street Gallery welcomes Betty Burbage and Elissa Crouch as guest artists for May and June in a show curated by local artist Lisa Krentel. […]
Cambridge Ghost Walk
Cambridge Ghost Walk
Take a walk down Haunted High Street in Historic Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange […]
Second Saturday Book Sale
Second Saturday Book Sale
The friends of the Library hold their Monthly Book Sale at the Cambridge location of the Dorchester County Library on the second Saturday of the […]
Cars & Carnitas at Taqueria Floritas
Cars & Carnitas at Taqueria Floritas
The restaurant Taqueria Floritas hosts Cars and Carnitas May 14 from 5 to 8pm with $1 tacos and $10 burritos. Questions? Call 443-225-5152. Address: 1721 […]
4 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Maryland Freedom Swim
Maryland Freedom Swim
NOTE: The May 15 date has not yet been confirmed. Registration will open once the date is finalized. The Maryland Freedom Swim is an open […]
NDVFD Poker Run & Bike Show
NDVFD Poker Run & Bike Show
Join in the Neck District Fire Company Poker Run & Bike Show Sunday, May 15. Registration opens at 9:30 a.m. at the Old Coast Guard […]
Sunday Gospel Jazz Brunch
Sunday Gospel Jazz Brunch
ArtBar 2.0 hosts an all-you-can-eat Sunday Gospel Jazz Brunch on May 1 from 12 to 4pm (and on most Sundays). Some Sundays feature live entertainment. […]
0 events,
0 events,
2 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Life Learning Leadership Coach at Bay Country Shop
Life Learning Leadership Coach at Bay Country Shop
Bay Country Shop hosts AliceAnne Loftus on May 18 from 10am to 3pm. Take The Lead – as an entrepreneur, speaker, author, and business coach […]
3 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Farmers Market
Cambridge Farmers Market
Find local produce, meats, cheeses, crafts, and more at the weekly Cambridge Farmers Market. In 2022, the market runs from May 5 through October 27. […]
Stars of the Banner/Hometown Heroes Celebration
Stars of the Banner/Hometown Heroes Celebration
As part of their Stars of the Banner/Hometown Heroes Celebration, the Dorchester Banner invites everyone to enjoy a free evening on the Choptank River. Mark […]
1 event,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
8 events,
Old Time May Day Celebration at Malone’s Church
Old Time May Day Celebration at Malone’s Church
The Harrisville/Malone Cemetery Maintenance Fund hosts May Day on May 21 from 12 to 4pm – "remembering our ancestors by connecting with our roots." The […]
Skipjack Sail
Skipjack Sail
Join the Skipjack Nathan of Dorchester – an authentic traditional oyster dredging vessel and Maryland's state boat – for a two-hour cruise on the Choptank […]
Skate, BMX, Stunt Day with RAR Brewing
Skate, BMX, Stunt Day with RAR Brewing
RAR Brewing hosts a day to celebrate all things skate, BMX, stunts – and beer – on May 21 in their taproom in Cambridge, MD. […]
Music on the Nanticoke Free Summer Concert Series
Music on the Nanticoke Free Summer Concert Series
Music On The Nanticoke Free Summer Concert Series kicks off May 21 from 4 to 7pm with The Stone Jack Ballers at the waterfront park […]
Cambridge Ghost Walk
Cambridge Ghost Walk
Take a walk down Haunted High Street in Historic Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange […]
Cambridge Classic Powerboat Regatta
Cambridge Classic Powerboat Regatta
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland! This year marks the 110th Cambridge Classic Power Boat Regatta […]
East New Market Community Day
East New Market Community Day
Join in the East New Market Community Day on May 21 starting at 11am at Friendship Park. All residents, friends, and supporters are welcome to […]
Comedy Night Featuring Ala Bama
Comedy Night Featuring Ala Bama
Join the ArtBar 2.0 May 21, 7-10pm for a night of Comedy and live music featuring Ala Bama and music by A Breathe of Fresh […]
4 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Classic Powerboat Regatta
Cambridge Classic Powerboat Regatta
The oldest active powerboat race in the country happens right here in Dorchester County, Maryland! This year marks the 110th Cambridge Classic Power Boat Regatta […]
Sunday Gospel Jazz Brunch
Sunday Gospel Jazz Brunch
ArtBar 2.0 hosts an all-you-can-eat Sunday Gospel Jazz Brunch on May 1 from 12 to 4pm (and on most Sundays). Some Sundays feature live entertainment. […]
A Harriet Tubman Musical Performance
A Harriet Tubman Musical Performance
Join Gil Cephas and the Soulful Groove Band (formerly known as Evolution) for live music at the Harriet Tubman Underground Railroad Visitor Center Pavilion on […]
1 event,
Plein Air Golf Tournament and Artist Showcase
Plein Air Golf Tournament and Artist Showcase
Golf and art join forces May 23, 2022 for a golf tournament and artist showcase. This signature fundraising event for the Dorchester Center for the […]
0 events,
1 event,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
3 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Farmers Market
Cambridge Farmers Market
Find local produce, meats, cheeses, crafts, and more at the weekly Cambridge Farmers Market. In 2022, the market runs from May 5 through October 27. […]
Project Clean Stream Trash Cleanup
Project Clean Stream Trash Cleanup
Looking to get outside and help clean your waterways? Join ShoreRivers and volunteers for one of the Project Clean Stream trash cleanups! To volunteer for […]
2 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Ghost Walk
Cambridge Ghost Walk
Take a walk down Haunted High Street in Historic Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange […]
7 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Skipjack Sail
Skipjack Sail
Join the Skipjack Nathan of Dorchester – an authentic traditional oyster dredging vessel and Maryland's state boat – for a two-hour cruise on the Choptank […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Birthday Bash at Layton’s Chance Winery
Birthday Bash at Layton’s Chance Winery
Layton's Chance Vineyard & Winery invites everyone to help them celebrate their 12th birthday on May 28 from 6 to 9pm. Music by Wavvy Gravy. […]
Beckwith Church Spring Festival
Beckwith Church Spring Festival
The Beckwith Church Spring Festival happens May 28 starting at 8am. The event happens at the Neck District Volunteer Fire Company, 954 Cooks Point Rd. […]
Healthy Kids Day
Healthy Kids Day
On Saturday, May 28 beginning at 10am, the Dorchester County YMCA hosts a Healthy Kids Day. There will be vendors, games, outdoor activities, food, drinks […]
2 events,
Choptank River Lighthouse to Baltimore Harbor Lighthouse Tour
Choptank River Lighthouse to Baltimore Harbor Lighthouse Tour
Join lifelong Dorchester County native, Capt. Phil Gootee on a full-day Chesapeake Bay lighthouse tour. This adventure departs from the Choptank River Lighthouse in Cambridge, […]
Sunday Gospel Jazz Brunch
Sunday Gospel Jazz Brunch
ArtBar 2.0 hosts an all-you-can-eat Sunday Gospel Jazz Brunch on May 1 from 12 to 4pm (and on most Sundays). Some Sundays feature live entertainment. […]
1 event,
Memorial Day Service
Memorial Day Service
The American Legion Post 91 is welcoming everyone to attend a Memorial Day Service on Monday, May 30 at 11am. The annual event will be […]
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
After being closed for two summers, Horn Point Lab is welcoming back the public to explore their science. Walk the Horn Point campus and learn […]
2 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Drums Along the Marshyhope
Drums Along the Marshyhope
The South Dorchester Folk Museum presents "Drums Along the Marshyhope" on Wednesday, June 1 at 7pm. The event will be held at the Robbins Heritage […]
2 events,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Farmers Market
Cambridge Farmers Market
Find local produce, meats, cheeses, crafts, and more at the weekly Cambridge Farmers Market. In 2022, the market runs from May 5 through October 27. […]
1 event,
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
5 events,
Skipjack Sail
Skipjack Sail
Join the Skipjack Nathan of Dorchester – an authentic traditional oyster dredging vessel and Maryland's state boat – for a two-hour cruise on the Choptank […]
Riverboat Cruise with Choptank Riverboats
Riverboat Cruise with Choptank Riverboats
Cruise on one of the most exciting attractions offered on Maryland's Eastern Shore... The Choptank Riverboat Company's The Dorothy & Megan and The Choptank River […]
Cambridge Ghost Walk
Cambridge Ghost Walk
Take a walk down Haunted High Street in Historic Cambridge – the most haunted street in Maryland! Hear about the ghosts who haunt and strange […]
Youth Fishing Fun Day
Youth Fishing Fun Day
In partnership with the Friends of Blackwater and the Harriet Tubman State Park, Blackwater National Wildlife Refuge will hold their annual Youth Fishing Fun Day […]
Virtual Prize Raffle for Vienna Volunteer Fire Company
Virtual Prize Raffle for Vienna Volunteer Fire Company
The Vienna Volunteer Fire Company will be hosting a Virtual Prize Raffle on June 4. They will be pulling tickets on Facebook Live starting at […]