September is one of the best months to be in Southern Maryland. The heat breaks, the county fairs open, and the waterfront towns fill up with events worth planning around. This is a full list of things to do in Southern Maryland September 2026, with confirmed dates and locations across Charles, St. Mary’s, and Calvert counties.
I grew up here and have worked across this region since 2011. When buyers relocating to Southern Maryland ask what the community actually looks like, September is a good answer. You get waterfront concerts in Solomons, a free lighthouse festival on the Potomac, farmers markets in Leonardtown, and three county fairs running back to back. It’s a full month.
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Early September: ArtWalk Weekend, Farmers Market, and Paddling on the Water
ArtWalk First Friday Weekend in Leonardtown (Sept 4-6)
The Town Square in Leonardtown kicks off September with its ArtWalk First Friday Weekend, running Friday September 4 through Sunday September 6. Galleries open late, local vendors fill the square, and there’s live music on Friday evening. This is one of Leonardtown’s recurring seasonal events and it draws a consistent crowd from across St. Mary’s County.
Leonardtown’s square has become one of the better walkable destinations in Southern Maryland. Restaurants, specialty shops, and galleries all within a few blocks. If you’ve thought about what it would be like to live close to Leonardtown, a First Friday weekend gives you a real look at the town on an active night.
First Saturday Farmers Market in Leonardtown (Sept 5)
The First Saturday Market Series continues September 5 in Leonardtown Town Square. Local produce, handmade goods, and food vendors. The series runs monthly through December, so September is a good time to start if you haven’t made it out yet.
Sultana Adult Paddling Experience (Sept 8)
The Sultana Projects program runs adult paddling experiences from Leonardtown on September 8. A hands-on way to see the creek and tidal shoreline from the water. Sultana Projects focuses on Chesapeake Bay education and environmental programming. A quieter alternative to the festival circuit if you want to get out on the water instead of standing in a crowd.
Mid-September Things to Do in Southern Maryland
ZZ Top at Calvert Marine Museum Waterside Pavilion in Solomons (Sept 11)
ZZ Top plays the Calvert Marine Museum Waterside Pavilion in Solomons on September 11 at 7pm. The outdoor waterfront venue sits right on the Patuxent River and it’s one of the better concert settings in the region. Tickets required. If you’ve never been to a show at the CMM pavilion, the setting alone is worth the drive from anywhere in the tri-county area.
Arrive early and walk the waterfront in Solomons before the show. The Calvert Marine Museum is worth visiting if you have time before gates open. Solomons Island has restaurants right along the water if you want dinner before the concert.
FamilyFest on the Potomac at Piney Point Lighthouse (Sept 12)
FamilyFest on the Potomac is a free annual event at the Piney Point Lighthouse Museum and Historic Park, 44720 Lighthouse Road, Piney Point. It runs September 12, hosted by the Friends of St. Clement’s Island and Piney Point Museums.
Live music, food vendors, kids activities, and access to the lighthouse grounds along the Potomac River. No admission charge. For families looking for things to do in Southern Maryland September 2026 that are free and good for all ages, this is one of the better options on the calendar. The lighthouse grounds on the Potomac are worth visiting on any clear day.
Charles County Fair in La Plata (Sept 17-20)
The Charles County Fair runs September 17 through September 20 at 8440 Fairgrounds Road, La Plata. Agriculture exhibits, 4-H competitions, carnival rides, livestock shows, and local food vendors. One of the most established community events in Charles County, drawing families from across the county every year.
The 4-H exhibits and livestock barns are worth the walk-through if you have kids. Entertainment runs most evenings on the main stage. Charles County has a strong agricultural tradition and the fair reflects it. If you’re thinking about putting down roots in Charles County, this gives you a feel for the community.
Outdoor Movie Night in Leonardtown (Sept 19)
Free outdoor movie night in Leonardtown Town Square on September 19. Bring a blanket or chairs. Leonardtown runs these through the warmer months as part of its community programming. Check the town’s schedule for the film and start time as it gets closer.
County Fair Season: Three Fairs Across Charles, St. Mary’s, and Calvert Counties
When people ask about things to do in Southern Maryland September 2026, the county fair circuit is the most consistent answer. September and early October are county fair season. All three major fairs run in sequence. If you’re new to the area or haven’t been in a few years, each county runs its own fair with a distinct feel.
St. Mary’s County Fair in Leonardtown (Sept 24-27)
The St. Mary’s County Fair opens September 24 at 42455 Fairgrounds Road, Leonardtown and runs through September 27. Four days of exhibits, food, rides, livestock competitions, and evening entertainment. One of the most attended events in the county each year, drawing people from across the tri-county area.
The fairgrounds are off Route 5 just outside of Leonardtown. Parking on-site. Weekend days draw the biggest crowds — Saturday especially. Families with younger kids often find weekday afternoons easier. The St. Mary’s County Fair is one of those traditions in the county that has been running for decades.
Paw Crawl in Leonardtown (Sept 27)
The Paw Crawl runs September 27 in downtown Leonardtown. Dog owners and their dogs walk through participating shops and restaurants in the Town Square area. Pet-friendly and free to join.
Calvert County Fair in Prince Frederick (Sept 30 through Oct 4)
The Calvert County Fair starts September 30 and runs through October 4 at 140 Calvert Fair Drive, Prince Frederick. The fair extends into early October, so if September fills up, you still have time in the first week of October to make it. Agriculture exhibits, carnival rides, entertainment, and local food. The Calvert fair tends to have a more relaxed pace on weekday afternoons compared to the larger St. Mary’s fair.
What September Says About Living in Southern Maryland
There are plenty of things to do in Southern Maryland September 2026 across all three counties, which makes it a practical month for relocating buyers to explore before choosing where to settle. One thing I tell buyers who are relocating here is to spend time in each county before choosing where to buy. Charles County, Calvert County, and St. Mary’s County each have a different feel. September’s event calendar is spread across all three in a way that makes it practical to actually do that in a single month.
I’ve been a real estate agent in Southern Maryland since 2011, born and raised here. If you’re thinking about what it’s like to live in this area, events like the county fairs, First Friday in Leonardtown, and the waterfront concerts in Solomons tell you more than any listing description will.
If you’re already a homeowner and thinking about whether fall is a good time to sell or make a move, I wrote about what the Southern Maryland housing market looks like heading into fall 2026. Current inventory and pricing without the spin. And if you’re an investor evaluating rental properties or fix-and-flip opportunities in the area, the post on real estate investing in Southern Maryland covers what I actually look for in this market.
September is also when families who moved here over the summer are just getting settled. If you have questions about the neighborhoods, what different parts of the county feel like day to day, or what the Maryland exit tax means if you’re selling, call or text me at (301) 751-9318. There are more things to do in Southern Maryland September 2026 than most people realize before they move here. Fourteen years here, no sales pitch.
Frequently Asked Questions: Things to Do in Southern Maryland September 2026
Ready to Buy or Sell in Southern Maryland?
If September’s events have you thinking about the area more seriously, I work with buyers and sellers across Charles, Calvert, St. Mary’s, and beyond. As an active investor, I’ll give you honest numbers on what the market looks like right now and whether it makes sense for your situation. Call or text (301) 751-9318 or fill out the form below.
Sources
- Leonardtown.com Events Calendar — ArtWalk First Friday Weekend, First Saturday Market, Paw Crawl confirmed dates
- SoMd.com Community Calendar — Charles County Fair, FamilyFest on the Potomac, Outdoor Movie Night dates
- Visit St. Mary’s County — FamilyFest on the Potomac — event details and Piney Point Lighthouse location
- Calvert Marine Museum — Waterside Pavilion concert venue
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