Start planning now for a great 2019 — here are 19 Dorchester events to watch out for! Check out our online calendar for more events. You can also download our 2019 Dorchester Events Guide or order hardcopy here.

1. Seafood & Canning Show & Sale, Feb. 17
Tokens, labels, crates, cans, and more reflect the heritage and stories of families and businesses on Maryland’s Eastern Shore and beyond.

2. Muskrat Weekend!  Feb. 22-24
Two unique events in one weekend, both celebrating the muskrat!
National Outdoor Show, Feb. 22-23: A slice of traditional Dorchester culture with muskrat skinning, duck calling, and more.
Crawfish Boil & Muskrat Stew Fest, Feb. 24: Outdoor festival (yes, in February!) with muskrat dishes and fresh crawfish. Plus the second annual Muskrat Leg Eating Contest!

3. Harriet Tubman Weekend, March 9-10
Join the Tubman Museum & Educational Center for the annual Tubman Banquet on March 9. Then head to the Tubman State Park & Visitor Center March 10 for a special day of inspiring talks, children’s activities, more. Underground Railroad hero Harriet Tubman lived and toiled in Dorchester County for more than 25 years.

4. Chicone Village Day at Handsell, April 27
Learn about Native American culture with demonstrations, crafts for kids, and a visit to an authentically built longhouse.

5. Burning of the Vines at Layton’s Chance Winery, May 3
Join in the fun as the previous season’s grapevines are burned. Bonfire, food trucks, music, and of course, wine.

6. Cambridge Classic Powerboat Regatta, May 19-20
Watch boats reach speeds up to 170mph on the Choptank River.

7. Cambridge Wings & Wheels, May 25
Check out cars, motorcycles, and planes displaying, demonstrating, and competing.

8. Boat Docking Contests
Dorchester County is home to four boat docking contests in 2019, when you can watch boat captains as young as 10 years old maneuver their boats with speed and skill.

Chamber Challenge Boat Docking – June 2

Suicide Bridge Boat Docking – Aug. 18

Taylors Island Boat Docking – Aug. 25

Hoopers Island Boat Docking – Sept. 8

9. Taste of Cambridge, July 13
Taste and vote on scrumptious crab dishes made by local restaurants, plus fun for kids, crab-picking competition, and music.

10. Seafood Feast-I-Val, Aug. 10
This belly-pleasing event features all-you-can-eat steamed crabs, fried fish, crab soup, fried clams, BBQ chicken, sides. Plus car show, live music.

11. Groove City Culture Fest, Aug. 17
Live music, vendors, food, and more celebrates the local African-American community.

12. Native American Festival, Sept. 14-15
Traditional dancing, drumming, crafts, food. In Vienna.

13. Choptank Heritage Skipjack Race, Sept. 21
Watch icons of the Chesapeake Bay take to the water. The race offers amazing close-up views of these traditional oystering boats.

14. Dorchester Center for the Arts Showcase, Sept. 22
Festival featuring regional artists and artisans offering their work for sale on Cambridge’s historic High Street. Plus food and music and fun for kids.

15. IRONMAN Maryland, Sept. 28
One of the world’s most grueling endurance events — 140.6 miles of swimming, biking, and running. (Dorchester hosts a second IRONMAN triathlon, IRONMAN 70.3 Eagleman — which is half the length — on June 9.

16. Crabtoberfest, Oct. 5
A mash-up of a traditional German Oktoberfest and Eastern Shore food.

17. Water/Ways Exhibit and More, Oct. 19-Nov. 30
Back Smithsonian traveling exhibit and local exhibit dive into water’s environmental and cultural impact.

18. The Kite Festival at Sailwinds Park, Oct. 27
Fun for all ages with kite flying, kids’ activities, face painting, food, and more. On the Choptank River.

19. Cambridge-Dorchester Christmas Parade & Lighting of the Crab Basket Tree, Dec. 7
Lighting of the Crab Basket Christmas Tree (yes, built out of 200+ baskets used by crabbers) kicks off this annual nighttime Christmas parade.

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