Holiday Activities For Families
🎁 Activities Around Town
🛍Markets, Shopping & Fairs
Christkindlmarkt – Downtown Denton
Thu Dec 4 • 5–9:30PM
Holistic Holiday Market – Nourish Moon
Thu Dec 4 • 6–8PM
Holiday Sales Event – Noude Aesthetics
Sat Dec 6 • 11AM–2PM
Christmas Bazaar
Sat Dec 6 • 12–5PM • Stevensville Middle
Heck With the Malls Holiday Market
Sat Dec 6 • 10AM–3PM • Centreville Arts
Oxford Holiday Market
Dec 12–14 • Oxford Community Center
Holiday Artisan Craft Fair – Patriot Acres
Sun Dec 14 • 12–4PM
Christmas Sip & Shop – Divine Faces & Elevated Aesthetics
Sun Dec 14 • 1–4PM • Easton
Santa’s Secret Handmade Vendor Fair
Sat Dec 20 • 12PM • Cult Classic Brewing
Island Flea Market Magic Awaits
Sun. Dec 21 • 11AM-4PM • Cult Classic Brewing
🎊Festivals & Parades
Federalsburg Tree Lighting
Fri Dec 5
Easton’s Holiday Parade
Sat Dec 6 • 6:30–10PM
Jingle Jubilee
Sat Dec 13 • 3–7PM • Matapeake
Christmas in Ridgely Winter Festival
Sat Dec 13 • 4–8PM
Christmas on the Creek – Oxford
Fri Dec 5
🎄Holiday Experiences & Family Activities
S’mores & Stories with a Ranger
Fri Dec 5 • 7–8PM • Matapeake Beach
Gingerboard House Competition
Sat Dec 6 • 9AM–12PM • Rock Hall
Jingle & Jam Nursery Express
Dec 6–7 • 12–4PM • Stevensville
Christmas Train Display
Sat Dec 13 • 10AM–4PM • Sudlersville
Drive-Thru Nativity – Centreville Methodist
Sat Dec 13 • 6–7PM
Christmas on the Farm
Sun Dec 14 • Federalsburg
Dominic’s Farm Christmas Party
Sat Dec 20 • 2–4PM
Santa Photos & Sightings
📸 Photos w/Santa & Santa Sightings
Christmas on the Creek – Oxford
Fri Dec 5 • 7:30–8PM • Port of Oxford (Santa sightings)
Annual Cookie Walk with Santa
Sat Dec 6 • 5–8PM • Town of Queenstow
Photos with Santa – Stevensville
Sat Dec 6 • 12P-4PM • Lowes Bayshore Nursery
Paws & Claus – Pet Pics with Santa
Fri Dec 12 • 5–8PM • Town of Ridgely
Bark the Halls – Pet Photos
Fri Dec 5 • 9–11AM • Matapeake Clubhouse, Stevensville
Breakfast With Santa – Rams Head Shore House
Sat Dec 13 • Santa 9–11AM / Breakfast 8–12PM • Stevensville
Christmas PAWTY – “Puppy & Me” Photos
Sat Dec 13 • 3–6PM • Dessert First Coffee & Desserts
Jingle Jubilee – Santa Visit
Sat Dec 13 • 3–7PM • Matapeake Beach & Clubhouse
Christmas on the Farm with Santa
Sun Dec 14 • 12–4PM • Federalsburg
Brunch w/ Santa
Sun Dec 14 & 21 9AM-12PM • Talbot Street Tavern
Dinner With Santa – Mamma Mia
Sun Dec 14 • 5–7PM • Centreville
Santa Comes to Groundwork
Sat Dec 20 • 10AM–1PM • St. Michaels
Christmas Pajama Brunch w/ The Grinch – Mamma Mia
Sun Dec 21 • 10AM • Centreville
Christmas in St. Michaels Boat Parade (Santa sightings)
Sat Dec 13 • 6PM • St. Michaels Harbor
Holiday Lights & Tree Lightings
🎄 Holiday Lights & Tree Lightings
Centreville Town Christmas Tree Lighting
Wed Dec 3 • 6:30–9:30PM • Centreville
Federalsburg Annual Tree Lighting
Fri Dec 5 • 6–9PM • Federalsburg
6th Annual Vendor Fair & Tree Lighting
Sat Dec 6 • 12–3PM • Fisherman’s Crab Deck, Kent Narrows
Historic Stevensville Holiday Lights
Sat Dec 6 • 4:30–6:30PM • Historic Stevensville
Winter Festival – Galena (Tree Lighting)
Sat Dec 6 • 5–8PM • Galena
Holiday Fun For Adults
🍷 Adults / Grown-Up Events
S’mores & Stories with a Ranger (late-night vibe)
Fri Dec 5 • 7–8PM • Matapeake
Holiday Open House (shopping, gifting, gift baskets & more)
Th. Dec 4 • 4-7PM • Chesapeake Chefs Market, Grasonville
Holistic Holiday Market (shopping vendors & free gifts)
Th Dec 4th 6–8PM • 1631 Event Venue, Stevensvill
Midnight Madness (shopping, food, bar crawl, raffles)
Fri Dec 6 • Day-Night• St. Michael’s
Ladies Night (cocktail & food specials)
Th Dec 6th 6–9PM • Corah’s Corner, St. Michael’s
Ugly Sweater Christmas Party
Sat. Dec 6th 6–9PM • Foxy’s, St. Michael’s
Sip & Shop
Th Dec 11th 6–8PM • Market at Dover Station
Historic Stevensville Holiday Lights (shopping + cocoa)
Sat Dec 6 • Evening
Candy Canes & Cocktails – Ladies Night @ Toptracer
Tue Dec 16 • 4–7PM • Queenstown
SantaCon Kent Island 2025
Date 13th • Adult 21+
Holiday Sip & Shop
Th Dec 19th 6–8PM • My Bella Jewel Boutique
Easton’s Crab Drop – NYE Celebration
Wed Dec 31 • 9PM–12AM
Cult Classic Markets & Events
(Handmade Market Dec 20 has adult-friendly shopping/drinks)
Holiday Fun For Pets
🐾 Holiday Fun for Pets
Bark the Halls – Free Pet Photos
Fri Dec 5 • 9–11AM • Matapeake Clubhouse
Paws & Claus – Pet Pics
Fri Dec 12 • 5–8PM • Ridgely
Christmas PAWTY – “Puppy & Me” Photos
Sat Dec 13 • 3–6PM • Dessert First Coffee
Christmas in Ridgely – Pets Welcome
Sat Dec 13 • 4–8PM • Ridgely
