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
S Sun
M Mon
T Tue
W Wed
T Thu
F Fri
S Sat
3 events,
Chesapeake Bay Lighthouse Tour
Chesapeake Bay Lighthouse Tour
Join lifelong Dorchester County native, Capt. Phil Gootee on a full-day Chesapeake Bay lighthouse tour. This adventure departs from Gootee’s Marina, aboard Capt. Phil’s 42-foot […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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 […]
0 events,
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
Dive into science and see the Bay the Horn Point way! Every Tuesday at 10am from Memorial Day through Labor Day, tours will be offered […]
3 events,
Caroline-Dorchester County Fair
Caroline-Dorchester County Fair
The Caroline-Dorchester County Fair on August 3-6 celebrates agricultural traditions and plain old-fashioned (and new-fashioned) fun. Look for displays of everything from sheep to horses, […]
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 […]
Talk: America’s First Line of Defense
Talk: America’s First Line of Defense
The South Dorchester Folk Museum presents a talk on "America's First Line of Defense" with Major General James Adkins, USA, retired, on Wednesday, August 3rd […]
4 events,
Caroline-Dorchester County Fair
Caroline-Dorchester County Fair
The Caroline-Dorchester County Fair on August 3-6 celebrates agricultural traditions and plain old-fashioned (and new-fashioned) fun. Look for displays of everything from sheep to horses, […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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. […]
6 events,
Caroline-Dorchester County Fair
Caroline-Dorchester County Fair
The Caroline-Dorchester County Fair on August 3-6 celebrates agricultural traditions and plain old-fashioned (and new-fashioned) fun. Look for displays of everything from sheep to horses, […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Farm Along with Emily
Farm Along with Emily
It will be hands on fun for our younger visitors every Friday this August! When children Farm Along with Emily, they will learn important aspects […]
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 […]
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 […]
6 events,
Kids Fishing Derby
Kids Fishing Derby
Bring the kids, ages 5-12, to enjoy a morning of fishing at Long Wharf Park in Cambridge from 9am to 12pm on August 6, 2022. […]
Caroline-Dorchester County Fair
Caroline-Dorchester County Fair
The Caroline-Dorchester County Fair on August 3-6 celebrates agricultural traditions and plain old-fashioned (and new-fashioned) fun. Look for displays of everything from sheep to horses, […]
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 […]
Handsell Historic Site: Summer Saturday
Handsell Historic Site: Summer Saturday
Handsell opens the doors to its historic house every Saturday during the summer, June 18 through late August. Stop by for tours between 11am and […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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 […]
4 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 […]
Chesapeake Bay Lighthouse Tour
Chesapeake Bay Lighthouse Tour
Join lifelong Dorchester County native, Capt. Phil Gootee on a full-day Chesapeake Bay lighthouse tour. This adventure departs from Gootee’s Marina, aboard Capt. Phil’s 42-foot […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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 […]
1 event,
Art in the Park – Great Marsh Park
Art in the Park – Great Marsh Park
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
Dive into science and see the Bay the Horn Point way! Every Tuesday at 10am from Memorial Day through Labor Day, tours will be offered […]
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 […]
Art in the Park – Linden Ave. Playground, Secretary
Art in the Park – Linden Ave. Playground, Secretary
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
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 […]
4 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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. […]
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre presents "Dog Sees God: Confessions of a Teenage Blockhead" August 11-14, 2022 as part of their new Student Lab Productions. Directed by Luci […]
4 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Farm Along with Emily
Farm Along with Emily
It will be hands on fun for our younger visitors every Friday this August! When children Farm Along with Emily, they will learn important aspects […]
Art in the Park – McCarter Park, Cambridge
Art in the Park – McCarter Park, Cambridge
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre presents "Dog Sees God: Confessions of a Teenage Blockhead" August 11-14, 2022 as part of their new Student Lab Productions. Directed by Luci […]
11 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 […]
Ribbon Cutting: Dorchester Women’s Mural
Ribbon Cutting: Dorchester Women’s Mural
Join in as the ribbon is cut for the new Dorchester Women’s Mural on August 13, 2022 from 10am to 12pm. The mural features 12 […]
Handsell Historic Site: Summer Saturday
Handsell Historic Site: Summer Saturday
Handsell opens the doors to its historic house every Saturday during the summer, June 18 through late August. Stop by for tours between 11am and […]
Winter Storm in Summer Show & Artist Reception – Main Street Gallery August 13 @ 5pm – 8pm
Winter Storm in Summer Show & Artist Reception – Main Street Gallery August 13 @ 5pm – 8pm
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Jazz at the Mural with Amy K. Bormet
Jazz at the Mural with Amy K. Bormet
On the second Saturday of each month, the Harriet Tubman Museum & Educational Center presents a live music performance right in front of the well […]
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre presents "Dog Sees God: Confessions of a Teenage Blockhead" August 11-14, 2022 as part of their new Student Lab Productions. Directed by Luci […]
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 […]
Duck Race Festival
Duck Race Festival
Join the fun of the Duck Race Festival on August 13 from 11am to 2:30pm along Court Lane in Cambridge, MD. Look for family-friendly activities, […]
4 events,
Chesapeake Bay Lighthouse Tour
Chesapeake Bay Lighthouse Tour
Join lifelong Dorchester County native, Capt. Phil Gootee on a full-day Chesapeake Bay lighthouse tour. This adventure departs from Gootee’s Marina, aboard Capt. Phil’s 42-foot […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Wine & Unwind with Joey Fulkerson
Wine & Unwind with Joey Fulkerson
Visit Layton's Chance Vineyard and Winery to Sip wine and enjoy live music with Joey Fulkerson! Date: August 14 from 1pm to 4pm No fee, no […]
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre: Dog Sees God: Confessions of a Teenage Blockhead
Groove Theatre presents "Dog Sees God: Confessions of a Teenage Blockhead" August 11-14, 2022 as part of their new Student Lab Productions. Directed by Luci […]
1 event,
Art in the Park – Meadows Park, Cambridge
Art in the Park – Meadows Park, Cambridge
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
Dive into science and see the Bay the Horn Point way! Every Tuesday at 10am from Memorial Day through Labor Day, tours will be offered […]
2 events,
Art in the Park – Handsell House, Vienna
Art in the Park – Handsell House, Vienna
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
Step and Show Drumline
Step and Show Drumline
The Cambridge Empowerment Center presents a Step Show and Drumline Talent Showcase on Aug. 17 from 4 to 7pm. At the Cambridge Empowerment Center, 615-B […]
3 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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. […]
WHCP Radio Event Series Fundraiser
WHCP Radio Event Series Fundraiser
Join WHCP Radio for three major music and cultural experiences in downtown Cambridge. Their fundraiser this year is an eclectic event mix, from indie rock […]
5 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Farm Along with Emily
Farm Along with Emily
It will be hands on fun for our younger visitors every Friday this August! When children Farm Along with Emily, they will learn important aspects […]
Art in the Park – Community Center, Hurlock
Art in the Park – Community Center, Hurlock
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
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 […]
Groove City Culture Fest
Groove City Culture Fest
The Groove City Culture Fest – organized by the Groove City Black Heritage & Culture Group – is one of the largest art and culture […]
5 events,
Governor Hicks Cup Log Canoe Races
Watch majestic log canoe boats race on the Choptank River and compete for the Governor Hicks Trophy Aug. 20-21, 2022. The race starts at the […]
Handsell Historic Site: Summer Saturday
Handsell Historic Site: Summer Saturday
Handsell opens the doors to its historic house every Saturday during the summer, June 18 through late August. Stop by for tours between 11am and […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Summer Pig Roast
Summer Pig Roast
Join in the Summer Pig Roast hosted by the Neck District Grill on Aug. 20, 2022 from 6 to 10pm. Live band, food, and drink. […]
Groove City Culture Fest
Groove City Culture Fest
The Groove City Culture Fest – organized by the Groove City Black Heritage & Culture Group – is one of the largest art and culture […]
3 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Groove City Culture Fest
Groove City Culture Fest
The Groove City Culture Fest – organized by the Groove City Black Heritage & Culture Group – is one of the largest art and culture […]
1 event,
Art in the Park – Friendship Park
Art in the Park – Friendship Park
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
Dive into science and see the Bay the Horn Point way! Every Tuesday at 10am from Memorial Day through Labor Day, tours will be offered […]
1 event,
Art in the Park – Mandala Pie Shop
Art in the Park – Mandala Pie Shop
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
2 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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. […]
4 events,
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
Farm Along with Emily
Farm Along with Emily
It will be hands on fun for our younger visitors every Friday this August! When children Farm Along with Emily, they will learn important aspects […]
Art in the Park – Neck District Firehouse, Cambridge
Art in the Park – Neck District Firehouse, Cambridge
Free County Summer Art Programs 1pm to 3pm Art in the Park brings creative arts experiences to the community. These events are open to all […]
Friday Night Jazz, R&B, Pop Concert with Ashley Watkins
Friday Night Jazz, R&B, Pop Concert with Ashley Watkins
Ashley Watkins, Flutist in Concert Friday, August 26 - 7-8:30pm Dorchester Center for the Arts - Cambridge Join in to hear Cambridge native and master […]
3 events,
Handsell Historic Site: Summer Saturday
Handsell Historic Site: Summer Saturday
Handsell opens the doors to its historic house every Saturday during the summer, June 18 through late August. Stop by for tours between 11am and […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
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 […]
3 events,
Taylors Island Boat Docking Challenge
Taylors Island Boat Docking Challenge
Don't miss this unique community event as our watermen (and women) show off their skills and battle for prizes by maneuvering their boats at breakneck […]
Winter Storm in Summer – Main Street Gallery
Winter Storm in Summer – Main Street Gallery
Main Street Gallery is delighted to have Cambridge artist Winter Storm, as guest artist for July and August. Her show of unique paintings and drawings […]
“Reflections on Water” Harp Recital at the Tubman Museum
“Reflections on Water” Harp Recital at the Tubman Museum
Harpist Kara Dahl Russell and her students will present a varied recital of music on Aug. 28, 2022 starting at 2pm at the Harriet Tubman […]
0 events,
1 event,
Horn Point Lab Tour
Horn Point Lab Tour
Dive into science and see the Bay the Horn Point way! Every Tuesday at 10am from Memorial Day through Labor Day, tours will be offered […]
0 events,
2 events,
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
Award winning acrylic painter, Maureen S. Farrell, is Main Street Gallery’s guest artist for September/October. Her show, “Imperfectly Perfect” highlights a collection of the artist’s […]
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. […]
2 events,
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
Award winning acrylic painter, Maureen S. Farrell, is Main Street Gallery’s guest artist for September/October. Her show, “Imperfectly Perfect” highlights a collection of the artist’s […]
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 […]
3 events,
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
“Imperfectly Perfect” – Fall Exhibit at Main Street Gallery
Award winning acrylic painter, Maureen S. Farrell, is Main Street Gallery’s guest artist for September/October. Her show, “Imperfectly Perfect” highlights a collection of the artist’s […]
Underground Railroad Walking Tour
Underground Railroad Walking Tour
Join Ranger Tim of the Harriet Tubman Underground Railroad National Historical Park on a free walking tour around downtown Cambridge, Maryland and discover the stories […]
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 […]