Labor Day Weekend Events

By Jim Meyer

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Crab race
National Hard Crab Derby
Photo By: Patty Hancock Photography
Defenders Day at North Point
Maryland Renaissance Festival
Maryland Renaissance Festival

With schools starting after Labor Day - 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. Photo By: Mitch Lebovic

1 Maryland State Fair 2019 - More Than a Fair, We're a Culture

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.

Maryland Renaissance Festival

2 Maryland Renaissance Festival

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


Learn More
family on pedal surrey on Ocean City Boardwalk Photo By: Clark Vandergrift

3 Maryland Week - Ocean City

TBD August /September 2019
Hooray-hooray school starts after Labor Day!!  Let's take advantage of this extra opportunity to enjoy Ocean City, with great discounts on hotels (excludes Labor Day weekend) and more. Enjoy a little more fun in the OC sun!

Crab race Photo By: Patty Hancock Photography

4 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


Learn More
photo of Street Rod Photo By: Western Maryland Street Rod Association

5 Western Maryland Street Rod Roundup

TBD August/September 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

Jazz Trio performing at festival Photo By: chesapeakemusic.org

6 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


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

7 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


More about Deal Island Skipjack Races and Island Fest


Type:
Events


Location:
Deal Island Harbor
Deal Island, MD 21821
410-784-2785


Learn More
Kayaking at Piney Run Park Photo By: Clark Vandergrift, OTD

8 Park Exploration & Get Into Nature Weekend

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


Learn More
Six Flags America Water Park Image Photo By: 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.

10 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
Musicians Perform at the Festival
03
Location:
40 E Dover St
Easton, MD 21601
Skipjack race
04
Location:
Deal Island Harbor
Deal Island, MD 21821
girl in woods
05
Location:
11100 Fort Frederick Rd
Big Pool, MD 21711
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