Labor Day Weekend Events

By Jim Meyer

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Crab race
National Hard Crab Derby
Image Credit: Patty Hancock Photography
knight on horseback
Maryland Renaissance Festival
Image Credit: Shelly Good Cook

Labor Day Weekend is a the perfect opportunity to make even more summer memories in Maryland. Here’s a list of ideas to get you inspired.

Plan your trip around the "11 Best Days of Summer" at the Maryland State Fair. Image Credit: Mitch Lebovic

1 Maryland State Fair 2019, Timonium

August 22-September 2, 2019
No other event provides so much food, fun and family entertainment for so little: tame and thrilling rides, classic and local foods, livestock, farm, garden, home exhibits, thoroughbred racing; live national concerts. It's more than the Maryland State Fair, it's a culture.

Maryland Renaissance Festival

2 Maryland Renaissance Festival, Crownsville/Annapolis

Weekends Aug. 24-Oct. 20, 2019
If you think four centuries back isn’t Ye Olde Enough for you....check out the annual Maryland Renaissance Festival in Crownsville near Annapolis.


More about Maryland Renaissance Festival


Type:
Events


Location:
1821 Crownsville Road
Annapolis, MD 21401
800-296-7304


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Crab race Image Credit: Patty Hancock Photography

3 National Hard Crab Derby & Fair, Crisfield

August 28-September 2, 2019
The 71st Annual National Hard Crab Derby & Fair will be a crab-extravaganza with crab races, crab picking and crab cooking. In addition, there will be boat docking contests, parade, games, rides, fireworks, arts/crafts, live entertainment and of course - fabulous seafood!
Crisfield


More about National Hard Crab Derby


Type:
Events


Location:
715 Broadway
Crisfield, MD 21817
410-968-2500


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photo of Street Rod Image Credit: Western Maryland Street Rod Association

4 Western Maryland Street Rod Roundup, Cumberland

August 30- September 1, 2019
Spend Labor Day Weekend at the Allegany County Fairgrounds for The Western Maryland Street Rod Roundup.  It's three days of high octane fun in Cumberland.
Allegany County Fairgrounds


More about Western Maryland Street Rod Roundup


Type:
Events


Location:
11490 Moss Avenue
Cumberland, MD 21502
301-697-0142


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Jazz Trio performing at festival Image Credit: chesapeakemusic.org

5 Monty Alexander Jazz Festival, Easton

August 30-September 1, 2019
Send off summer with the scintillating sounds of jazz at this Labor Day favorite. Ten years in and growing every summer, make the trip once, and this one is sure to become an annual tradition. You won’t want to miss this classic concert, also make sure to check out our Summer of Music page for more great music festivals and concerts.


More about Monty Alexander Jazz Festival


Type:
Events


Location:
40 E Dover St
Easton, MD 21601
410-822-7299


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Deal Island Harbor hosts this race each Labor Day Weekend. The event also features a fishing contest and delicious local food.

6 Deal Island Skipjack Races & Island Festival

August 31 - September 2, 2019
Deal Island is The Real Deal! The festival will include parades, a fair, local food, car show, live music, the blessing of the boats, Smith Island Skiff Race and the legendary Skipjack Race - where boats and hard working crews battle to be the "fastest in the fleet."
Somerset County

White Marlin jumping out of the water

7 Annual Labor Day White Marlin Tournament

August 29-September 1, 2019
This will be a spectactular weekend for fishing, and big fish = big $$!
The 61st Annual Labor Labor Day White Marlin Tournament hosted by the Ocean City Marlin Club is open to everyone. Tight lines!


More about Annual Labor Day White Marlin Tournament


Type:
Events


Location:
9659 Golf Course Road
Ocean City, MD 21842
410-213-1613


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Fort Frederick

8 Park Exploration & Get Into Nature Weekend, Big Pool

August 31- September 2, 2019
Bring your family and friends to explore the natural side of Fort Frederick State Park with self-guided and staff-led outdoor nature and recreation activities for all.
Big Pool


More about Park Exploration Weekend at Fort Frederick


Type:
Events


Location:
11100 Fort Frederick Rd
Big Pool, MD 21711
301-842-2155


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Six Flags America Water Park Image Image Credit: Six Flags America

9 End of Summer Family Fun

We may be in the “R” months, but you don’t have to let your summer slip away. The water is still warm, the sun is still shining, and Maryland is definitely the place to be in September; with the kids not back in school until after Labor Day, you can enjoy a longer Summer. Check out our September's Summer Sendoff page for other great family fun suggestions.

Baltimore has the foodie experience for you, whether it's local seafood or bombastic burgers and beer. Image Credit: Visit Baltimore

10 Delicious Labor Day Events

Allegany County Mountain Maryland Restaurant Week - Rise and dine in Mountain Maryland during this Labor Day weekend of culinary delights.
Baltimore Vegan Restaurant Week - Restaurants are challenged to demonstrate their love and compassion for promoting healthier diets, and reducing environmental impacts.

The Awakening - National Harbor Image Credit: the_ly_edition-Instagram

11 More Labor Day Ideas

Sounds like a lot to do, but there’s always more in Maryland! For more great Labor Day getaways, check out our Events Calendar

Featured Places
Renaissance Festival
01
Location:
1821 Crownsville Road
Annapolis, MD 21401
National Hard Crab Derby
02
Location:
715 Broadway
Crisfield, MD 21817
antique car
03
Location:
11490 Moss Avenue
Cumberland, MD 21502
Monty Alexander at the piano
04
Location:
40 E Dover St
Easton, MD 21601
OCMC logo
06
Location:
9659 Golf Course Road
Ocean City, MD 21842
girl in woods
07
Location:
11100 Fort Frederick Rd
Big Pool, MD 21711
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