October Events in Southern Maryland

October is right around the corner and with it brings fall colors, a chill in the air, and Halloween fun. Southern Maryland has many events to kick off the fall, and here are a few for you and your family to enjoy.

Fall Farm Fun

There are many farms in Southern Maryland that offer pumpkin patches, hayrides, corn mazes, petting zoos, moon bounces, and even more to enjoy as fall starts to creep in. These festive events will last all of October at multiple farms throughout the area. Here are some great farms that allow plenty of family fun.

Bowles Farm, Clements, MD

This farm is open on the weekends from 10 a.m. to 6 p.m. Admission is $10, and kids 3 and under are free.

Forest Hall Farm and Orchard, Mechanicsville, MD

Open on the weekends from 9 a.m. to 5 p.m. Admission is $10, and kids 3 and under are free.

Butlers Orchard, Germantown, MD

Butlers Orchard is open on the weekends, and admission is $12, while kids under 2 are free.

Milburn Orchard, Elkton, MD

Open weekends from 10 a.m. to 5 p.m. Admission is $10, and kids under 2 are free.

Blessing of the Fleet

St. Clement Island Museum

Saturday, October 5th and Sunday, October 6th

Taking place for over 50 years, this time-honored tradition of blessing the fleet of watermen’s boats offers something for everyone. Tours of the Blackistone Lighthouse and the St. Clement Island Museum will be available, as well as live entertainment and free boat excursions. Enjoy the local fare and wines of Southern Maryland while watching the fireworks, or join in on the activities for children and adults alike.

A Taste of Southern Maryland Wine Tour

Waldorf, MD

Saturday, October 5th from 10:30 a.m. to 7 p.m.

Jack and Jill of America, Inc, invite you to join in on their annual wine tour amongst the stunning landscape of Southern Maryland. Enjoy great wine, premium craft beers, and appetizers. The night ends with a tour with dinner and dancing at the Blue Crab Stadium Legends Club. Tickets sell for $85.00 per person and include transportation, tastings, and dinner.

53rd Annual US Oyster Festival

Leonardtown, MD

Saturday, October 19th from 10 a.m. to 6 p.m. and Sunday, October 20th from 11 a.m. to 6 p.m.

There’s no better way to kick off oyster season than at the Southern Maryland Oyster Festival.  Enjoy a day on the Chesapeake Bay with live music, great food, craft beers, and all around family fun. Learn about the life of a waterman, enjoy the national oyster shucking competition, and get your fill of fresh oysters.

2nd Annual Blue Crabs, Beer, Food and Wine Fest

Southern Maryland Blue Crabs Stadium

Saturday, October 26th from 12 p.m. to 7 p.m.

If you’re a food lover, you’ll find many great choices at the Blue Crabs, Beer, Food and Wine Fest. With over 100 vendors, you will definitely need to bring your appetite. This event is full of locally prepared food, locally brewed beer, and locally grown wine. Vendors will include local wineries, breweries, and restaurants, as well as nationally known brands such as Pampered Chef, Sensy, and LulaRoe.


October brings the beginning of autumn as well a lot of fun filled events. Get ready to have fun with your family on a farm or to go to a beer & wine festival. What are your favorite fall activities?

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