Holiday events in Leonardtown

• Sat, 29 Nov, 2025 - 11:00 AM

  Holiday Sip & Shop

  22695 Washington St, Leonardtown, MD

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

  Live Holiday Music w/ Doc Lohn - December First Friday!

  22660 Washington St., Leonardtown, MD, United States, Maryland 20650

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

  Wreaths & Wine Dec 6th

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

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

  Tinsel and Tape: Holiday Wrapping Workshop

  The Fenwick Inn

  USD 8
• Sat, 29 Nov, 2025 - 09:00 PM

  Naughty or Nice DJ Night

  22695 Washington St, Leonardtown, MD

  41+ Interested
• Sat, 06 Dec, 2025 - 11:30 AM

  SMCARA HOLIDAY GATHERING

  25470 Point Lookout Rd, Leonardtown, MD 20650

  6+ Interested
• Sun, 07 Dec, 2025 - 10:00 AM

  Baked & Boozy: Baked Goods Sip & Shop

  22695 Washington St, Leonardtown, MD

  361+ Interested
• Sat, 29 Nov, 2025 - 10:30 AM

  Wreaths & Wine Nov

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

  97+ Interested
• Sun, 07 Dec, 2025 - 12:00 PM

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

  Shepherd's Old Field Market

  368+ Interested
• Tue, 16 Dec, 2025 - 04:00 PM

  MTC Holiday Meet-Up | Leonardtown Scavenger Hunt

  The Inn at Leonardtown

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

  Holiday Dressage Schooling Show 🎄

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

  58+ Interested
• Mon, 01 Dec, 2025 - 06:00 PM

  Healthy Holidays

  23140 Moakley St. Suite 6, Leonardtown, MD, United States, Maryland 20650

  5+ Interested
• Sun, 07 Dec, 2025 - 11:00 AM

  North End Gallery's Annual Holiday Jewelry Trunk Show

  41652 Fenwick St, Leonardtown, MD, United States, Maryland 20650

  4+ Interested
• Sat, 06 Dec, 2025 - 09:00 AM

  Fur Babies with the Grinch and Holiday Market

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

  47+ Interested
• Sat, 20 Dec, 2025 - 09:00 AM

  Pictures with Santa Clause

  Town Market LLC

  87+ Interested