St. Mary's County
Fall Trip Planning Guide
Fall in St. Mary's means breathtaking leaves, warm apple cider, perfectly plump pumpkins, and, of course, the iconic U.S. Oyster Festival! This guide will help you plan the perfect autumn getaway as St. Mary's turns to stunning shades of orange, red, and yellow, with crisp weather, pumpkin patches, corn mazes, warm drinks, and special memories just waiting to be made.
Autumn in the Outdoors
Explore corn mazes, pumpkin patches and fall treats throughout the county at Forrest Hall Farm, Dixon Family Farm and Lyon Family Farms or find delicious, local produce at one of the local farmers markets. Stop by Southern Maryland's largest corn maze at Bowles Farms for their 25th Anniversary starting September 27th!
St. Mary's County Fair
Enjoy four days of fun from Sep 18 - Sep 21 with rides, games, food, vendors, music, and so much more. Meet all sorts of farm animals in the barns, and browse the handiwork that's been entered into a variety of competitions including home arts, farm and garden, arts and crafts.
Leonardtown, known as "A Most Convenient Place", has plenty to do during the fall season. Check out the fall-themed First Fridays, Scarecrow Stroll and the Tractor and Truck show!
Historic St. "Scary's" City
From the elegant and eerie Vampire Manor (21+) to the slightly spooky Lost City Trick or Treat, there is Halloween fun for everyone in Historic St. Mary's City (HSMC)! Don't forget to explore beyond the events, as HSMC is a museum of living history and archaeology telling diverse stories on the site of Maryland’s first capital in beautiful, tidewater Southern Maryland.
59th Annual U.S. Oyster Festival
Enjoy fresh oysters, oyster shucking contests, live entertainment, shopping, family-friendly fun, and more at the U.S. Oyster Festival held October 18th and 19th in St. Mary's County.
Getting Hungry? Taste the county's food and drink specialties from local restaurants, food trucks, caterers and craft beverage makers at the Taste of St. Mary's on September 27th!
Find your Perfect Place to Stay
If you want convenient and affordable, we’ve got it! There are extended-stay hotels, romantic weekend getaways and plenty of rooms with a view.
Taste the Craft Beverage Trail
Let your taste buds bloom in St. Mary's with handcrafted beer, wine, cider, and spirits. With artisans crafting everything from beer and wine to cider and coffee, there's no shortage of flavor on the trail! Try the trail in one place at the Thirsty Thursday at Aeropark on September 18th!
See Maryland International Raceway's biggest and fastest race of the year at the 29th annual Haltech World Cup Finals from November 5th through 9th!
Check this page regularly to see what fall favorite events are happening soon!
