Holiday Events in Talbot County, MD (2026): Lights, Tree Lightings and Markets
Photo: Farragutful, CC BY-SA 4.0, via Wikimedia Commons
Talbot County does Christmas on the water. St. Michaels marks its 40th Christmas weekend this year, with a parade on Talbot Street and lighted boats on the Miles River. Here's our 2026 list for St. Michaels, Easton and Oxford, with the dates, times, costs and addresses we checked in early November. Tap any photo to go straight to the event's page.
Before you go: holiday hours and weather can change plans, so check the event's website the day you head out.
Talbot County holiday events, in date order
Inn at Perry Cabin Holiday Lights
When: From Saturday, Nov. 28
Cost: Free to see
Good to know: The inn's entry drive is lit for the whole season.
Where:St. Michaels, MD 21663
Event page:tourtalbot.org/holidays-in-st-michaels
Christmas in St. Michaels
Photo: Christmas in St. Michaels. Tap the photo for the event page.
When: Dec. 11 to 13
Cost: Some events need tickets
Good to know: Includes a tour of historic homes, a holiday marketplace and a gingerbread display.
Where:St. Michaels, MD 21663
Event page:christmasinstmichaels.org/events
Winter on the Chesapeake and the Lighted Boat Parade
Photo: Talbot County Tourism. Tap the photo for the event page.
When: Saturday, Dec. 12: festival from 1 p.m., boat parade at 6 p.m.
Cost: See website
Good to know: Live music, food, crafts and carriage rides at the museum, then lighted boats on the Miles River. The Talbot Street Parade is that morning at 10:30.
Where:Chesapeake Bay Maritime Museum, 213 N. Talbot St., St. Michaels, MD 21663
Event page:tourtalbot.org/holidays-in-st-michaels
Christmas on the Creek in Oxford
When: December (2026 schedule coming soon)
Cost: See website
Where:Oxford waterfront, Oxford, MD 21654
Event page:portofoxford.com/event/christmas-on-the-creek-in-oxford-md
Talbot County holiday events: quick answers
When is Christmas in St. Michaels in 2026?
Dec. 11 to 13, 2026. The Talbot Street Parade is Saturday, Dec. 12 at 10:30 a.m., and the lighted boat parade on the Miles River is that evening at 6.
Make it a holiday quest
How many can you check off before New Year's? A tree lighting, a lights show and a holiday market. One is Elf level, two is Reindeer, all three is Santa. Tag us on Instagram when you finish your quest.
More Maryland holiday guides
Visiting family in another county? Our Maryland holiday events guide links to every county we cover. Maryland holiday events by county
Thinking about home in Talbot County?
If the holidays have you thinking about a move within Talbot County or anywhere in Maryland, or you're just curious what your home is worth, we're happy to help. No pressure.
We're Steven and Jacqui Saucedo of The Saucedo Team. For more than 10 years we've helped people buy and sell homes across Maryland, and we're proud to be one of the top-performing teams in the DMV and one of the top bilingual (English/Spanish) teams in the region. Questions about your home or the market? Reach out anytime at steven@thesaucedoteam.com or (240) 778-8260.
We welcome everyone, and we follow federal, Maryland and DC fair housing laws in every home search and sale.
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