Octoberfest First Friday Weekend @ Town of Leonardtown

Friday, October 2nd Leonardtown kicks off the season with the 8th 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 live music with Sam Grow from 6pm-8pm.
 

Saturday, October 3rd 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 58th 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 Courthouse parking lot. Dedicated golf carts will be shuttling attendees up and down the hill.
 

Sunday, October 4th 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.