2025 Holiday Guide to Maryland’s Eastern Shore

Your complete guide to festive events, parades, Santa visits, and seasonal celebrations across the Shore.

Welcome to the Most Festive Season on the Shore🎄

Maryland’s Eastern Shore shines during the holidays, offering charming small-town celebrations, waterfront parades, historic tours, family activities, and magical light displays. Whether you're looking for Santa sightings, festive markets, or cozy winter events, this guide highlights the best of the 2025 holiday season.

✨ Festive Activities

Talk to Rudolph — Easton

Nov 26–Dec 24 — Talbot Town Shopping Center
Mon–Sat: 10 AM–9 PM | Sun: 10 AM–6 PM
A local favorite! Stop by and “call” Rudolph while enjoying the Santa House throughout the month.

 Santa House Schedule:
 Friday 12/12, 12/19: 5 PM - 7 PM
 Saturday 12/6: 3 PM - 5 PM & 12/13, 12/20: 12 PM - 2 PM
 Sunday 11/30, 12/21: 12 PM - 2 PM

Cambridge Christmas Train Garden

Dec 1–31 (closed Christmas)
Mon–Fri: 6–9 PM | Sat–Sun: 1–4 PM & 6–9 PM
The nation’s longest-running fire department holiday train display, filled with miniature scenes and Christmas magic.

Frosty’s Holiday Village — Easton

Dec 5 | 5–7:30 PM at Anchor Church
Enjoy free family activities including photos with Frosty, holiday treats, crafts, and a showing of Frosty’s Winter Wonderland.

The Nutcracker — Cambridge

Dec 13 | 11 AM & 3 PM
A beautiful performance by the Eastern Shore Dance Academy.

🎉 2025 Holiday Parades

Mark your calendar for this year’s lineup of festive parades:

• Nov 28 — Chestertown (5:30–8 PM)

• Dec 4 — Denton (6 PM), Berlin (7 PM)

• Dec 5 — Centreville (6:30 PM)

• Dec 6 — Easton (6:30 PM), Cambridge (5 PM), Tilghman Island (5 PM), Ocean City (11 AM)

• Dec 7 — Salisbury (1 PM)

• Dec 13 — St. Michaels (10:30 AM parade + 6 PM Boat Parade), Hurlock (5 PM)

🎄Holiday Events

Christkindlmarkt — Denton

Dec 4 | 5–9:30 PM
Carriage rides, local vendors, warm drinks, and handcrafted holiday gifts.

A Dickens of a Christmas — Chestertown

Dec 5–6
Step into 1840s London with entertainment, tours, food, and Dickens-inspired fun.

Ice Ice Berlin

Dec 6 | 5–8 PM
Ice sculptures, light displays, tree lighting, and late-night shopping.

Midnight Madness — St. Michaels

Dec 6
Late-night shopping, live music, and prize drawings.

Winter Festival — Galena

Dec 6
Santa visits, cookies, hot chocolate, and a tour of the town’s best holiday lights.

Crab Basket Tree Lighting — Grasonville

Dec 6 | Vendor fair at noon, lighting at 6 PM
A true Eastern Shore tradition.

Candlelight Tour of Historic Homes — Centreville

Dec 6 | 12–4 PM
Explore historic homes decorated for the holidays.

Festival of Trains — Kent Narrows

Dec 6–7 & 13–14
A multi-weekend train festival benefiting the restoration of Centreville Station Freight Depot.

Mistletoe on Main — Cambridge

Dec 7
A full day of holiday markets, Santa events, caroling, and more.

Christmas in St. Michaels

Dec 12–14
A weekend full of home tours, shopping, Santa visits, and the iconic Lighted Boat Parade.

Jingle Jubilee — Stevensville

Dec 13 | 3–7 PM
Free, family-friendly festivities at Matapeake Beach & Clubhouse.

🎅 Santa’s Stops

Find Santa across the Shore all season long:

• Nov 28 — Chesapeake Bay Outfitters, St. Michaels

• Dec 3–4 — Skate with Santa, Easton - Talbot County Community Center

• Dec 7 — Breakfast with Santa, Cambridge - Bull Provisions & Smokehouse

• Dec 13 & 20 — Santa’s Workshop, Denton - Wharves of Choptank Visitor Center

• Dec 20 — Cookies with Santa, Hurlock - Christ United Methodist Church

🍽️ Holiday Dining & Carryout

Skip the cooking and enjoy holiday meals from local favorites including:

• Hunter’s Tavern — Easton

• Suicide Bridge Restaurant — Hurlock

• Hyatt Regency — Cambridge

• Deep Blue at Knoxie’s Table — Stevensville

• Caroline Culinary Arts — Denton

• Village Shoppe — St. Michaels

🎆 New Year’s Eve Celebrations

Ring in 2026 at one of these Eastern Shore celebrations:

• Easton — Downtown NYE Celebration (6 PM–12 AM)

• Chestertown — Imperial NYE Dinner

• St. Michaels — Ruse NYE

• Ocean City — New Years on the Island at Fager’s

• Berlin — 6 PM Street Celebration

• Rock Hall — Potluck at The Mainstay

• Salisbury — Downtown NYE Festival (9 PM–12:30 AM)

☕ Cozy Coffee Shops

Warm up with a seasonal latte at:

• Rise Up Coffee

• Black Water Bakery

• Weather Gage

• Java Rock

• A Little Lovely Coffee House

Wrap-Up

Whether you’re planning festive family outings, holiday shopping trips, or cozy winter weekends, Maryland’s Eastern Shore is full of ways to celebrate the season. Bookmark this guide and enjoy every magical moment.