Leonardtown's Square Closes to Cars Twice in November, and the Same Lots Up the Hill Serve Both Days
October 29, 2026
October 29, 2026
Leonardtown's two biggest downtown gatherings this November both close Washington and Fenwick Streets into the Square. On both days the town sends spectators to the same parking lots at the Governmental Center and the College of Southern Maryland. The Veterans Day Parade closes the streets on a weekday morning. Christmas on the Square closes them on a Friday afternoon and keeps them closed into the night. In between, and through December, the town's calendar shifts from weekend-long events to single days, and most of those single days happen on one block of Washington Street.
For anyone who lives in or near town, the dates matter less than the hours. Knowing when the streets close is the difference between an easy morning on the Square and a slow loop around Lawrence Avenue.
From May through October, the Leonardtown Business Association's First Friday runs as a weekend-long event. October's Octoberfest ran Oct. 2 through Oct. 4. November drops back to the year-round format, where galleries, restaurants, cafés and shops open their doors on the first Friday of the month, and the event fits into one day.
The Nov. 6 theme is "Passport to the Holidays." The LBA hasn't posted 2026 details yet. In 2025, The BayNet described the same theme as a free shop-and-stroll challenge spread across a weekend. Rubber ducks were hidden in more than 15 businesses, and people collected passport stamps to enter for prizes. This year's version falls on a single Friday, so last year's format may not carry over.
Two fixed points on Nov. 6 have confirmed hours:
The next morning, Saturday, Nov. 7, the Coastal Arts Market runs at Leonardtown Wharf, 22510 Washington Street, from 9 a.m. to 3 p.m. It is also the first holiday season for What The Fizz Beverage Boutique at 22699 Washington Street. The BayNet reported its grand opening on Aug. 7 in the space Kneaded Bakery used to occupy.
The Annual Veterans Day Parade falls on Wednesday, Nov. 11, 2026. It steps off from St. Mary's Ryken High School at 10 a.m., proceeds through town, and is followed right away by a Memorial Ceremony in Leonardtown Square. The Commissioners of Leonardtown and the Commissioners of St. Mary's County are the hosts.
The streets close two hours before the parade starts. The town's page says Washington Street and Fenwick Street into downtown close to traffic from 8 a.m. until noon. During that window, downtown parking and through traffic are limited to areas reached from Lawrence Avenue, and only for residents, business owners and employees. Deputies from the St. Mary's County Sheriff's Office handle traffic control.
Spectators are directed to three lots:
Families with kids marching in the parade have their own instructions. Marching groups park at Leonardtown Middle School between 7:45 and 9 a.m., and the last shuttle to Ryken leaves at 9. The town asks parents not to drop children off at Ryken, along the roadside, or at the intersection.
If the weather turns, the parade is canceled and the Memorial Ceremony moves inside Leonardtown Town Hall, 22670 Washington Street. The town will make the call by 8 a.m. that day and post it on the parade page, the Town of Leonardtown Facebook page and the St. Mary's County Government website.
The streets reopen at noon, and that is when the day moves out of town. Port of Leonardtown Winery holds a Veterans Day event from noon to 6 p.m., billed as following the parade, with live music from Jeff Warner, food trucks and local vendors.
Two weeks later, the Square closes again for a much longer stretch. Christmas on the Square & the Annual Tree Lighting Ceremony is Friday, Nov. 27, 2026, the day after Thanksgiving. Festivities start at 4:30 p.m. with holiday music, sleigh rides, train rides, hayrides, a live nativity, balloon art, face painting, children's crafts, hot drinks and food. It ends with Santa's arrival. The event is free. The Commissioners of Leonardtown, the Leonardtown Volunteer Fire Department and the Leonardtown Business Association are the sponsors.
The town marks its posted closure and parking plan as tentative. Here is how it compares with the parade morning:
| Veterans Day Parade, Nov. 11 | Christmas on the Square, Nov. 27 | |
|---|---|---|
| Downtown closure | Washington and Fenwick, 8 a.m. to noon | Square, including Washington and Fenwick, 1 to 10 p.m. |
| Satellite parking | Fairgrounds, Governmental Center, CSM | CSM, Governmental Center, Leonardtown Library/Garvey Senior Center |
| Shuttle | Only for marching groups, from Leonardtown Middle School | Free for the public, 4:15 to 9 p.m., to St. Aloysius Church lot |
| Bad weather | Ceremony moves into Town Hall | No rain date; may be canceled |
The Governmental Center and CSM are on both lists. Christmas on the Square is the only one of the two with public shuttles. The town's plan has buses picking up at CSM, the Governmental Center and the Leonardtown Library/Garvey Senior Center and dropping off at St. Aloysius Church parking lot downtown. At the Governmental Center, the stop is across from the Carter Building, marked with a red "Shuttle Pick Up Sign." At the library, the stop is at the front of the building, reached from Hollywood Road by Leonard's Grant Parkway and Hayden Farm Lane.
Parking at St. Mary's Ryken, the Blackbelt Academy lot on Gregory Drive, and the grass lots along Courthouse Drive near Fenwick Street has no shuttle, so you walk in from those. People living around Tudor Hall are told to enter town by Lawrence Avenue, because access to Courthouse Drive will be restricted. Courthouse Drive, Guyther Drive, Camalier Drive and parts of Park Avenue, Shadrick Street, Pope Street and Church Street will also have very limited access.
Two timing details shape the evening. Fire truck rides shut down at 6:45 p.m. so cars can leave town safely after Santa arrives. And the page's weather note still shows last year's date for the cancellation decision, so the Town of Leonardtown Facebook page is the place to check that morning.
The same day starts earlier on Washington Street. The LBA calendar lists a Holiday Market with The Grinch and Cindy Lou Who at 22675 Washington Street from 10 a.m. to 7 p.m. on Nov. 27. The Square closes to through traffic and parking at 1 p.m., so if you want to drive in, shop and leave before the crowds arrive, go before then.
After the tree lighting, the season turns into a string of smaller dates, and 22675 Washington Street, home of the Town Market, hosts most of them. Between the LBA calendar and the winery's own event pages, the month looks like this:
None of these dates come with posted street closures, and each one is a single-day event.
Gingerbread Lane gets the December First Friday name, and it is also a set of displays placed around town. The LBA's Gingerbread Lane page describes four-foot wooden gingerbread cutouts decorated by businesses, community groups, sports teams, families and friends. This is its second year. When registration opened in July, The BayNet reported that the displays are spread throughout the community and that last year's participants can reuse their characters. That means some of this year's figures may be familiar ones from last season. The same LBA announcement opened registration for the 8th Annual Scarecrow Stroll, the fall version of the same idea.
If you're hosting family in town for Thanksgiving weekend or the December Saturdays and want ideas for where to take them, or you're curious how this season's busy Square fits with life in Leonardtown year-round, Theresa Shoptaw is glad to talk it through. Let's Connect.
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