October 3rd – 5th, 2025
It is
shaping up to be a jam-packed First Friday Weekend in Leonardtown, and
you won’t want to miss it! From festive fall fun to live entertainment and
beloved annual traditions, there is something for everyone to enjoy. Here is
what’s happening around town:
Friday, October 3rd
Leonardtown kicks off the season with the 7th Annual Scarecrow Stroll!
Dozens of whimsical and creative scarecrows will be on display throughout town
for the entire month of October. Be sure to cast your vote for your favorite!
Stick around in the Square for a surprise performance at 5:30pm,
followed by an evening of live music with Wes Ryce from 6–8pm Bring a
chair, grab a bite, and soak in the fall vibes!
Saturday, October 4th
Start your Saturday morning with the Friends of the Poor Walk, hosted by
St. Vincent de Paul Society, taking place downtown from 9am–12pm While
no roads will be closed, drivers should watch for increased pedestrian traffic.
Brief delays may occur as walkers cross the streets.
Later in the day, the 57th Annual Blessing of the Fleet, coordinated by
the 7th District Optimist Club, gets underway at 12pm down at
Leonardtown Wharf. Please note:
- No public parking will be available at the
Wharf from 7am–10pm
- Traffic on Wharf Hill will be
restricted to handicap parking and Wharf residents only.
- Event attendees are encouraged
to park at the College of Southern Maryland and ride the convenient
trolley service to the Wharf.
Sunday, October 5th
Cap off the weekend with the always-popular Antique Tractor and Truck Parade
from 1–3pm in Leonardtown Square! Please be aware of the following road
closures:
- No parking in the Square and
surrounding areas starting at 11am until 3:30pm.
- No thru-traffic in the Square
starting at 12:30pm until 3:30pm.
And that’s not all—local businesses throughout Leonardtown will
also be hosting a variety of activities and specials, from live music and
touch-a-truck fun to unique events and seasonal promotions.
