October is the best month to be outside in Southern Maryland. The humidity is gone, the Chesapeake Bay is still warm enough for fishing and kayaking, and the county has a slate of events that actually makes it worth putting on a calendar. Here is a full list of things to do in Southern Maryland in October 2026, with confirmed dates and locations across Charles, Calvert, and St. Mary’s County.
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U.S. Oyster Festival. October 17 and 18, Leonardtown
This is the one. The U.S. Oyster Festival at the St. Mary’s County Fairgrounds is one of the oldest oyster festivals in the country and it draws serious crowds. The 2026 festival runs Saturday, October 17 from 10am to 6pm and Sunday, October 18 from 11am to 6pm at 42455 Fairgrounds Road in Leonardtown.
The centerpiece is the U.S. National Oyster Shucking Championship, where competitive shuckers from around the country race for speed and technique. Beyond the contest, you get oysters prepared every way possible. raw on the half shell, fried, grilled, steamed, Rockefeller, stew. Live music runs all weekend. Tickets are available at the gate and in advance through the festival website. If you are planning to be in Southern Maryland that weekend for any reason, this is worth building your schedule around.
The fairgrounds are easy to reach from Route 5 heading south from La Plata or Waldorf. Parking is on-site. Plan for crowds Saturday afternoon.
Calvert County Fair. Through October 4, Prince Frederick
The Calvert County Fair runs September 30 through October 4, 2026. The first few days of October overlap with the fair, making it an easy early-October outing for families in Charles and Calvert County. It is held at the Calvert County Fairgrounds in Prince Frederick.
Expect carnival rides, 4-H animal shows, food vendors, and the usual fair staples. It is one of the lower-key county fairs in the region. smaller than PG County, which is exactly why families from Prince Frederick and Huntingtown tend to prefer it. Not overwhelming. Good for kids.
First Friday in Leonardtown. October 2
Leonardtown runs First Friday events through October, and the October 2 edition includes an opening reception at the St. Mary’s County Arts Council Gallery and Gift Shop from 5 to 8pm. The fall show theme is “A Harvest of Haunts,” featuring work from gallery artists. Free to attend. The gallery is located in downtown Leonardtown, a short walk from the town square restaurants.
First Fridays in Leonardtown are worth knowing about if you live nearby and have not been. Downtown Leonardtown has gotten better over the last few years. a handful of solid restaurants, small shops, a waterfront park that faces the St. Mary’s River. The October edition with Halloween-themed art is one of the better-attended ones.
Patuxent River Appreciation Day. October 10, Solomons Island
Patuxent River Appreciation Day on October 10 is a free, community-focused event in the Solomons Island area celebrating the river that runs through the heart of Southern Maryland. It typically includes environmental education, kayak tours, and demonstrations from local conservation groups.
Solomons Island in October is worth a trip on its own. The summer crowds are gone, the restaurants are easier to get into, and the waterfront views of the Patuxent where it meets the Chesapeake Bay are at their best in fall light. Check the Calvert County event calendar for updated times and location details as October gets closer.
Fall Outdoor Activities Worth Planning Around
Beyond the scheduled events, October opens up a handful of outdoor activities in Southern Maryland that are harder to enjoy other times of year.
Calvert Cliffs State Park
The 35-million-year-old fossil beds at Calvert Cliffs are always worth a visit, but October hiking through the pine forest on the way to the beach is something different. The trail is about 1.8 miles each way. Fossils. mostly shark teeth. wash up on the beach at the base of the cliffs. Bring a bag. Entrance is free with a day-use fee of $3 per vehicle. Located on Route 2 south of Lusby.
Point Lookout State Park
Point Lookout is where the Potomac River meets the Chesapeake Bay. the southernmost tip of St. Mary’s County. In October, striped bass (rockfish) season opens on the Chesapeake, making Point Lookout one of the better spots to fish from shore or a boat. The park also has a Civil War museum, walking trails, and a small beach. Day-use fee applies.
Kayaking the Patuxent River
October water temperatures on the Patuxent are typically still comfortable enough for kayaking through mid-month. Several launch points exist around Prince Frederick, Solomons, and Broomes Island. This is also when the river banks start to turn. foliage along the Patuxent in October is better than most people expect from the region.
Pumpkin Patches and Fall Farms
Several farms across Charles and Calvert County open pumpkin patches and corn mazes in October. Dates and pricing vary. check local farm social media pages or the Charles County tourism calendar for the current season’s lineup. This is a reliable activity type for the region every October, though specific farm schedules can change year to year.
A Note on Living Here Year-Round
When people ask me for things to do in Southern Maryland in October, I usually tell them the list is longer than they expect. One thing I notice working with buyers and sellers across Southern Maryland: people who have lived here a long time sometimes undersell it to newcomers. They forget that the Oyster Festival is genuinely one of the best regional food festivals in the Mid-Atlantic, that Calvert Cliffs is one of the only places on the East Coast where you can find your own fossils, and that October fishing in the Chesapeake Bay draws people from three states.
Southern Maryland is not the loudest market. It does not have the name recognition of Annapolis or the beach crowds of Ocean City. But for the people who live here. in Waldorf, in Prince Frederick, in Leonardtown, in Solomons. October is one of the months that makes the decision to stay feel obvious. If you are considering a move to Charles County or anywhere else in this area, I am happy to talk about what neighborhoods look like from the inside, not just on paper. Reach out here or call (301) 751-9318.
Trunk or Treat and Halloween Events in Southern Maryland
Southern Maryland has more trunk or treat events in October than most people realize. Between Charles, Calvert, and St. Mary’s counties there are typically 30 or more events spread across the month. Most are free and community-run. The list below reflects annual events that have been held in prior years. Confirm specific dates and locations as October approaches since details for 2026 may shift. BayNet.com publishes the most complete running list as events are announced.
Trunk or Treat Events in Charles County
Charles County has the highest volume of Halloween events in Southern Maryland. The largest is the Family Fall FunFest at Melwood Recreation Center in Nanjemoy, held on Halloween night and featuring trunk or treat, outdoor movies, and a glow dance party. The Shops at Waldorf Center hosts a Spooky Fall Fest in mid-October with a petting zoo and live entertainment. The Rec Xpress Fall Festival at Bensville Park is a free afternoon event with food trucks, a DJ, and a costume contest. Downtown La Plata runs a Trick-or-Treat Trail along local businesses on the square. The Charles County Sheriff’s Office hosts a trunk or treat at the lower courthouse parking lot in La Plata, and Mall-O-Ween at St. Charles Towne Center runs on Halloween night with mall-wide trick or treating for all ages.
Trunk or Treat Events in Calvert County
Calvert County’s biggest Halloween event is Halloween in the Garden at Annmarie Sculpture Garden and Arts Center in Solomons, which typically draws over 60 candy booths, live music, and a DJ dance party. Halloween at Hallowing Point Park in Prince Frederick is a free county-hosted evening with food trucks and games. The North Beach Boo Bash runs along Bay Avenue with a costume parade and downtown business trick or treating. The Optimist Club of Calvert hosts a trunk or treat at the Calvert County Fairgrounds, and Tract-or-Treat at Mrs. Moo’s Corner Market adds a farm-style option with a costume contest and prize for best trunk.
Trunk or Treat Events in St. Mary’s County
St. Mary’s County has some of the most distinctive Halloween events in the region. Historic St. Mary’s City hosts a “Lost City” Trick-or-Treat with lantern-lit paths through Maryland’s first colonial capital on a Saturday in mid-October. Lyon Family Farms in Mechanicsville holds a Tractor Treat with farm equipment, food trucks, and yard games. The Patuxent River Naval Air Museum in Lexington Park hosts a Trunk-or-Treat on the Flight Line, with kids in costume receiving free admission with a paid adult. The Leonardtown Town Market on the square hosts a trunk or treat with classic cars and local vendors. St. Mary’s County Animal Services in California combines trunk or treat with a same-day pet adoption event, which is worth a visit if you have kids.
Frequently Asked Questions About Things to Do in Southern Maryland in October
When is the U.S. Oyster Festival in 2026?
The 2026 U.S. Oyster Festival is October 17 (Saturday, 10am-6pm) and October 18 (Sunday, 11am-6pm) at the St. Mary’s County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD 20650.
What is there to do in Solomons Island Maryland in October?
In October, Solomons Island is a good time to visit. crowds are down from summer, restaurants are accessible, and the waterfront is at its best in fall light. Patuxent River Appreciation Day falls on October 10. Kayaking, fishing, the Calvert Marine Museum, and waterfront dining are all solid options through mid-October.
Are there pumpkin patches near Waldorf or La Plata Maryland?
Yes, there are pumpkin patches and fall farm activities in Charles County each October. Specific farms and dates vary year to year. check the Charles County Department of Tourism calendar or local farm social media pages for current season listings.
Is October a good month to move to Southern Maryland?
October is actually one of the better months to close on a home in Southern Maryland. Inventory is typically lower than spring, which means less competition, and the market tends to be more negotiable. Families who close in October or November are often in their homes by the holidays. If you are thinking about buying or selling, I am happy to walk through the current numbers. Call (301) 751-9318.
What county is Leonardtown Maryland in?
Leonardtown is the county seat of St. Mary’s County, Maryland. It sits on Breton Bay off the Potomac River, about 70 miles south of Washington, D.C. via Route 5 or Route 235.
Ready to Buy or Sell? Start Here
There is no shortage of things to do in Southern Maryland in October, and this is also one of the better months to buy or sell. I work with buyers and sellers across Charles, Calvert, St. Mary’s, Prince George’s, and Anne Arundel County. If you are thinking about a move. this fall or next spring. I am happy to give you honest numbers on what the market looks like right now. No sales pitch.
Disclaimer: Event dates and details are sourced from official organizer websites and county tourism pages as of September 2026. Events are subject to change. Verify dates, times, and admission with the organizer before attending.
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