September Events in Southern Maryland

Summer is winding down, so make sure to get out and enjoy the last month of warm weather before the chill rolls in. All the September events in Southern Maryland offer something for everyone. Here’s a highlight of events not to be missed:

National Hard Crab Derby & Fair

Where: Somers Cove Marina, Crisfield

When: Monday, September 2nd

If you’re a fan of crab, the 71st annual National Hard Crab Derby & Fair is a must see. Enjoy a day of crab races, crap picking, and of course, crab eating. Bring the family and watch the boat docking contest, parade, and fireworks. Kids will be thoroughly entertained with arts & crafts and games while the parents can enjoy live entertainment and fabulous seafood options. This Derby is a Labor Day tradition, so make sure you don’t miss out.

Leonardtown Summer Music Festival

Where: Historic Leonardtown


Friday, September 6th @ 5:00 pm – 8:00 pm

Saturday, September 7th @ 2:00 pm – 6:00 pm

The Leonardtown Summer Music Festival offers something for everyone, from family-friendly events to more adult oriented evenings. The majority of the concerts are free, and you can even order a picnic from participating restaurants in town. You also have the option to enjoy a kid-free evening with Drop N’ Dine, where children will be entertained with kid-friendly activities at participating businesses (by reservation only). This festival is winding down in the last few days of summer, so head over before the last concert on the 7th.

A Taste of St. Mary’s 2019

Where: Leonardtown Square

When: Saturday, September 14th @ 1:00 –  5:30 pm

Make sure to come hungry to A Taste of St. Mary’s. Set in the historic Leonardtown Square, this popular annual event is foodie heaven. Sample unique creations from local restaurants and caterers while enjoying the free live entertainment, kids activities, and classic car show. Make sure to get a raffle ticket for a chance to win gift certificates from the participating vendors.

St. Mary’s County Fair

Where: St. Mary’s County Fairgrounds


Thursday, September 19th @ 4:00 pm – 9:00 pm

Friday, September 20th @ 9:00 am – 9:00 pm

Saturday, September 21st @ 9:00 am – 9:00 pm

Sunday, September 22nd @ 9:00 am – 7:00 pm

Come on out to celebrate at the St. Mary’s County Fair. Enjoy the carnival and fair food, or explore the various exhibits ranging from livestock, 4-H and school entries, flower and field crops, home arts, and more. Your kids will love the pig races and horse pulls.

Maryland Lighthouse Challenge

Where: Piney Point Lighthouse Museum, Point Lookout Lighthouse, St. Clement’s Island


Saturday, September 21st, 2019 8:00 am –  6:00 pm

Sunday, September 22nd, 2019 8:00 am –  6:00 pm

The Maryland Lighthouse Challenge is a great opportunity to explore Maryland’s historic lighthouses on a two day driving tour. There are eleven participating lighthouses and each one offers a complimentary souvenir. If you’re able to see all eleven, you get a special souvenir at the end. Some of the participating lighthouses include Piney Point Lighthouse, Lookout Lighthouse, and the Blackistone Lighthouse replica.

Coastal Arts Market at the Wharf 

Where: Leonardtown Wharf

When: Saturday, September 28th @ 9:00 am – 3:00 pm

This outdoor arts market is full of artistic and creative vendors all selling their unique and handcrafted wares. Set on the stunning Leonardtown Wharf, this market is one of a kind as there are no manufactured items for sale. Explore the park and shop to your heart’s content.


September is a great month for events in Southern Maryland. Enjoy the warm weather and fun filled activities that are offered. Do you have any favorite fall traditions? Share with us below.

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