Tomorrow events in Leonardtown in December

• Sat, 06 Dec, 2025 - 09:00 AM

  First Saturday of the Month Market Series

  22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD

  94+ Interested
• Sat, 06 Dec, 2025 - 10:30 AM

  Wreaths & Wine Dec 6th

  23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650

  77+ Interested
• Fri, 05 Dec, 2025 - 06:00 PM

  Affair On The Square

  22740 Washington Street, Leonardtown, MD 20650

  35+ Interested
• Sat, 20 Dec, 2025 - 08:00 PM

  Social’s Naughty Santa Party!

  41655 Fenwick St, Leonardtown, MD

  150+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  Hope In Harmony Winter Concert Series - Noel

  Leonardtown High School

  51+ Interested
• Sat, 13 Dec, 2025 - 09:00 AM

  Holiday Dressage Schooling Show 🎄

  41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD

  33+ Interested
• Wed, 31 Dec, 2025 - 08:00 PM

  Socials Obsidian Masquerade

  41655 Fenwick St, Leonardtown, MD

  38+ Interested
• Sat, 27 Dec, 2025 - 06:00 PM

  Sound bath Journey

  22660 Washington St

  USD 27
• Sun, 07 Dec, 2025 - 12:00 PM

  Photos with Grinch! (Pet **all species** and kid friendly)

  Shepherd's Old Field Market

  290+ Interested
• Thu, 11 Dec, 2025 - 06:00 PM

  Tinsel and Tape: Holiday Wrapping Workshop

  The Fenwick Inn

  USD 8
• Tue, 16 Dec, 2025 - 04:00 PM

  MTC Holiday Meet-Up | Leonardtown Scavenger Hunt

  The Inn at Leonardtown
• Sun, 14 Dec, 2025 - 12:00 PM

  Photos with Santa! (Pet **all species** and kid friendly)

  Shepherd's Old Field Market

  80+ Interested
• Mon, 15 Dec, 2025 - 07:00 PM

  St. Maries Choral Arts Home Concert Carol Sing

  First Saints Community Church

  70+ Interested
• Sat, 20 Dec, 2025 - 02:00 PM

  SoMD Santa Social - Free Photos, Crafts, & Cookies with Santa!

  Clark's Rest Community

  38+ Interested
• Sat, 27 Dec, 2025 - 02:00 PM

  Bob Pinnola and Rosa Hance at Port of Leonardtown Winery on December 27th, 2pm-5pm

  Port of Leonardtown Winery

  6+ Interested