November in Southern Maryland is one of the most underrated months of the year. The summer crowds are gone, the weather turns crisp, and the region has a full calendar of events worth getting out for. Whether you are in Charles County, Calvert County, or St. Mary’s County, there is plenty happening in November 2026, from Veterans Day parades and fall hikes to the start of the holiday season and one of the best light shows in the Mid-Atlantic. Here is your complete guide to things to do in Southern Maryland in November 2026.
| Date | Event | Time |
|---|---|---|
| Sun, Nov 1 | Southern Maryland Bluegrass | All day |
| Fri, Nov 6 | Italian Dinner Night | Evening |
| Sat, Nov 7 | Fall Artisan Market at Summerseat | All day |
| Sat, Nov 7 | Coastal Arts Market | All day |
| Sat, Nov 7 | FOL Fall Used Book Sale | All day |
| Sat, Nov 7 | PHVFD Shrimp Dinner | Evening |
| Sat, Nov 7 | Murder Mystery: Back to the 8s | Evening |
| Sun, Nov 8 | VFW All-You-Can-Eat Brunch Buffet | Morning |
| Sun, Nov 8 | Fall Foliage Hike | All day |
| Sun, Nov 8 | Holiday Shopping Event | All day |
| Mon, Nov 9 | Pax River Quilters Guild Meeting | All day |
| Wed, Nov 11 | Veterans Day Parade, Leonardtown | 10:00 am |
| Wed, Nov 11 | Calvert Marine Museum Veterans Day | All day |
| Fri, Nov 13 | Campfire Program, Calvert County | Evening |
| Sat, Nov 14 | Quarter Auction Benefit | Afternoon |
| Sat, Nov 14 | SMTMD Contra Dance | Evening |
| Thu, Nov 19 | Pressed Flower Luminary Workshop | Afternoon |
| Thu, Nov 19 | By Firelight and Starlight, Annmarie | Evening |
| Sat, Nov 21 | Thanksgiving 5K | Morning |
| Sat, Nov 21 | St. John’s School Christmas Bazaar | All day |
| Sun, Nov 22 | Fall Craft Show | All day |
| Sun, Nov 22 | Community Thanksgiving Service | Evening |
| Fri, Nov 27 | Annmarie Garden in Lights, Opens | Evenings |
| Sat, Nov 28 | Small Business Saturday | All day |
| Sat, Nov 28 | North Beach Tree Lighting | 4:00–7:00 pm |
| Sat, Nov 28 | Light Up the Season, Waldorf Center | 6:00–8:00 pm |
| Mon, Nov 30 | Chesapeake Beach Tree Lighting | 4:00–6:00 pm |
Early November: Fall Markets, Foliage, and Election Day
The first weekend of November is a strong one for things to do in Southern Maryland in November 2026. On Saturday, November 7, the Fall Artisan Market at Summerseat returns with local makers, crafters, and food vendors. The same day, the Coastal Arts Market in Calvert County runs alongside the Friends of the Library Fall Used Book Sale. Both are free to browse and worth the stop if you are in the area.
Sunday, November 8 brings a Fall Foliage Hike, one of the better outdoor activities in the region this time of year. Late fall in Calvert County means mostly bare trees with the last golden leaves clinging on, and the view toward the Chesapeake Bay through the tree line is worth lacing up your boots for. The same weekend, local VFW halls in the area are holding all-you-can-eat brunch buffets, which have become a reliable Sunday morning tradition for Southern Maryland families.
Tuesday, November 3 is Election Day 2026. Several local churches and civic organizations are running Election Day take-out meal fundraisers. This is a Southern Maryland tradition that doubles as community fundraising and a convenient dinner option if you are heading to the polls.
A few more events fill out early November for things to do in Southern Maryland in November 2026. On Sunday, November 1, Southern Maryland Bluegrass brings live acoustic music to the area. Thursday evening, November 6, the Italian Dinner Night is a community dinner worth adding to the calendar. Saturday evening, November 7 also has a Murder Mystery dinner event running for a different kind of night out. The Pax River Quilters Guild holds its monthly meeting on Monday, November 9, and is open to local fiber arts enthusiasts and visitors.
Veterans Day in Southern Maryland: November 11, 2026
Veterans Day is one of the biggest community days of the year in St. Mary’s County. The annual Veterans Day Parade in Leonardtown steps off at 10 a.m. on November 11, starting at St. Mary’s Ryken High School and marching into Town Square. The parade features local high school marching bands, military units, color guards, classic cars, fire and emergency vehicles, and elected officials. It is one of the most genuinely local events you will find in Southern Maryland. No corporate sponsors, just the community showing up.
Immediately following the parade, spectators are invited to stay in Town Square for a Veterans Memorial ceremony with patriotic music, wreath-laying, and words of remembrance. Parking is available at the St. Mary’s County Fairgrounds and the St. Mary’s County Governmental Center, with free shuttle service into downtown Leonardtown.
The Calvert Marine Museum in Solomons also hosts Veterans Day programming on November 11, including firsthand veteran accounts and artifact displays. If you have family or clients with military ties, this is one of the most meaningful things to do in Southern Maryland in November 2026.
Mid-November: Oyster Season, Workshops, and Local Markets
Oyster season in Maryland runs October 1 through March 31, which means November is prime time for fresh local oysters at waterfront restaurants in Solomons, St. George Island, and along the Patuxent River. This is not a ticketed event. It is a November dining tradition in Southern Maryland that regulars plan around. Check the menu at local waterfront spots before you go, and call ahead on weekends.
Friday, November 14 brings a Quarter Auction Benefit and the SMTMD Contra Dance, a long-running community dancing event that is surprisingly fun if you have never tried it. No experience required, and the callers walk you through every move. If you prefer the outdoors, Friday, November 13 has a Campfire Program running in Calvert County for an easy low-key evening.
Thursday, November 19 has two standout options. The Pressed Flower Luminary Workshop is an indoor hands-on craft evening and a good option for a date night or a group outing. The same evening, “By Firelight and Starlight” runs at Annmarie Sculpture Garden in Solomons. It is an outdoor experience at the garden that tends to sell out, so check ahead for tickets.
Thanksgiving Week: Races, Craft Shows, and Community Gatherings
The week of Thanksgiving is packed for things to do in Southern Maryland in November 2026. Friday, November 21 has the Thanksgiving 5K and Prediction 5K in the morning, a community race that draws a strong local crowd and is casual enough for first-timers. The same weekend, St. John’s School Christmas Bazaar kicks off the holiday shopping season early with local vendors and handmade gifts.
Saturday, November 22 features the Fall Craft Show, one of the larger indoor markets of the season. Local artisans, crafters, and food vendors fill the hall, and it is a reliable place to find Southern Maryland-made gifts before the holiday rush. The Community Thanksgiving Service on the same evening brings together local churches for a joint service, a tradition in both Charles and St. Mary’s County that reflects the community feel that makes Southern Maryland worth living in.
Small Business Saturday falls on November 28 this year. Downtown Leonardtown, La Plata, and Prince Frederick all have local shops worth supporting. The Shops at Waldorf Center in Charles County holds their annual Light Up the Season event the same evening from 6 to 8 p.m., with a tree lighting and new this year, a menorah lighting for Hanukkah. In Calvert County, North Beach holds their tree lighting on November 28 from 4 to 7 p.m. with food and beverage vendors, pop-up shops, and artisan crafts along the waterfront.
Annmarie Garden in Lights: The Best Weekend Activity in November
Annmarie Garden in Lights opens November 27 and runs through January. This is the highlight of the late-November calendar for things to do in Southern Maryland, and it is not close. The Annmarie Sculpture Garden in Solomons, Calvert County transforms into a lighted walking experience after dark, with illuminated trees, sculptures, and pathways through the woodland garden. It runs Thursday through Sunday evenings through the holiday season.
This is genuinely one of the most beautiful things you can do in Calvert County in November or December. It is popular, and timed tickets are required. Book in advance at annmariegarden.org before it sells out on weekend evenings. Plan for about 90 minutes on the grounds.
If you are relocating to Southern Maryland and wondering what the fall and winter social calendar looks like here, Annmarie Garden in Lights is a good answer. It is the kind of event that does not exist in most suburban markets outside the region.
Late November Tree Lightings: Chesapeake Beach on November 30
Chesapeake Beach in Calvert County wraps up November with their tree lighting on Sunday, November 30 from 4 to 6 p.m. at Chesapeake Beach Town Hall. The event includes visits and photos with Santa, a local Christmas market, and a performance by the Beach Elementary String Orchestra. It is a low-key, genuinely local event that is a good alternative to bigger, more crowded holiday events. The drive down Route 261 through North Beach is worth it in November.
A Note on Living in Southern Maryland
Southern Maryland in November is quieter than it is in the summer, but it is far from empty. The community events listed here represent the year-round rhythm of life in Charles, Calvert, and St. Mary’s County. This is the kind of calendar that keeps people here long after they move for a job at Pax River or a first assignment at NAS Patuxent River. If you are considering buying a home in Southern Maryland and want to know what the region is actually like to live in, November is an honest answer.
I have been buying and selling in Southern Maryland since 2011. I know these counties well. If you have questions about neighborhoods, commute times, or what different price points look like in Calvert, Charles, or St. Mary’s, I am happy to talk through it. Use the form below or call (301) 751-9318.
Frequently Asked Questions: Things to Do in Southern Maryland in November 2026
When does Annmarie Garden in Lights start in 2026?
Annmarie Garden in Lights opens November 27, 2026 and runs through January. It operates Thursday through Sunday evenings at the Annmarie Sculpture Garden in Solomons, Calvert County. Timed tickets are required and sell out on weekend evenings. Book in advance at annmariegarden.org.
What time is the Veterans Day Parade in Leonardtown in 2026?
The Leonardtown Veterans Day Parade steps off at 10 a.m. on Wednesday, November 11, 2026, starting at St. Mary’s Ryken High School and ending at Leonardtown Town Square. A Veterans Memorial ceremony with wreath-laying follows immediately after the parade in the town square. Free parking and shuttle service is available from the St. Mary’s County Fairgrounds and the Governmental Center.
Are there oyster festivals in Southern Maryland in November?
Maryland’s oyster season runs October 1 through March 31, making November prime oyster time in Southern Maryland. While dedicated oyster festivals typically happen in September and October, waterfront restaurants in Solomons, St. George Island, and along the Patuxent River serve fresh local oysters throughout November. Call ahead on weekends as demand is high.
Where are the tree lighting events in Southern Maryland in November 2026?
Three tree lighting events are confirmed for late November 2026. North Beach in Calvert County holds their lighting on November 28 from 4 to 7 p.m. with waterfront vendors and pop-up shops. The Shops at Waldorf Center in Charles County holds Light Up the Season on November 28 from 6 to 8 p.m., including a new menorah lighting this year. Chesapeake Beach hosts their tree lighting on November 30 from 4 to 6 p.m. with Santa photos and live music from the Beach Elementary String Orchestra.
What outdoor activities are available in Southern Maryland in November 2026?
November is a good month for hiking in Southern Maryland before winter sets in. Calvert Cliffs State Park offers trails with late fall foliage and Chesapeake Bay views. The Thanksgiving 5K in St. Mary’s County on November 21 is open to all fitness levels. Annmarie Garden in Lights starting November 27 provides a scenic evening outdoor walk through the sculpture garden in Solomons. The fall weather is typically mild enough for waterfront walks along the Patuxent River and in North Beach through late November.
Planning a Move to Southern Maryland?
Events like these are part of what makes Southern Maryland a place people stay. Whether you found this page searching for things to do in Southern Maryland in November or you are actively looking at homes in the area, the community calendar here is one of the things buyers are often surprised by. If you are considering buying a home in Charles, Calvert, or St. Mary’s County and want honest guidance on neighborhoods, prices, and what daily life looks like here, reach out below. No pressure, no script. Just someone who has worked this market for 14 years and lives here too.
Disclaimer: Event details are based on information available as of October 2026. Dates, times, and locations are subject to change. Confirm directly with event organizers before attending. This post is for informational purposes only.
Sources
- somd.com Community Calendar: November 2026 event listings for Southern Maryland
- Visit St. Mary’s County: Veterans Day Parade and local event information
- Annmarie Sculpture Garden: Garden in Lights schedule and ticketing
- The BayNet: Southern Maryland community event coverage