Leave a Message

Thank you for your message. We will be in touch with you shortly.

Home Search
Background Image

Holiday Guide to Maryland’s Eastern Shore

Explore the most festive holiday events and celebrations on Maryland’s Eastern Shore!

Whoville

Visit Whoville Village in Greensboro for lights, activities, and festive fun with the Grinch!
 
Nov 29-30 & Dec 6-7 & 13-14, 2024

Festival of Trees

Talbot Hospice’s biggest fundraiser offers festive trees, gifts, and entertainment at The Tidewater Inn.
 
November 30-December 3, 2024

Christkindlmarkt

Shop local gifts and enjoy food, drinks, and carriage rides in Downtown Denton, 5–9:30 PM!
 
December 5, 2024

A Dickens of a Christmas

Experience 1840s London in Chestertown with entertainment, tours, food, and festive fun!
 
December 6-7, 2024

Festival of Trains

The 2024 Festival of Trains at Kent Narrows supports restoring Centreville’s historic depot!
 
December 7-8 & 14-15, 2024

Midnight Madness

St. Michaels will glow with Christmas charm, late-night shopping, live music, and giveaways!

December 7, 2024

Deck the Town Hall

Celebrate in Galena with Santa, festive treats, and a dazzling light tour!

December 7, 2024

Crab Basket Tree Lighting

A tree lighting, vendor fair, crafts, and Santa at Fisherman’s Crab Deck!

December 7, 2024

Candlelight Tour of Historic Homes

Explore historic homes, enjoy caroling, and cider, and shop local crafts in Centreville, 12–4 PM.

December 7, 2024

Christmas in St. Michaels

Celebrate Christmas with home tours, breakfast with Santa, a boat parade, shopping, and music.

December 13-15, 2024

Mistletoe on Main

Holiday fun in Cambridge with Santa, a market, a cocktail crawl, and more!

December 14, 2024

Jingle Jubilee

Jingle Jubilee at Matapeake Beach offers free entry, gifts, Santa, and hot food from 4–7 PM.

December 21, 2024
 

Festive Activities

Don’t miss out on these special holiday activities available for a limited time!

Talk to Rudolph: Be sure to stop by the Talbot Town Shopping Center from November 27 to December 24 and give Rudolph a call! The center is open Monday through Saturday from 10 AM to 9 PM and Sunday from 10 AM to 6 PM.

Winterfest of Lights: Experience the 2024 Winterfest of Lights in Ocean City, MD, at Northside Park from November 21 to December 31, 5:30–9:30 PM. Open Wed-Sun until Dec 22 and daily Dec 23–31.

Train Garden: The Cambridge Rescue Fire Company’s Christmas Train Garden, the nation’s longest-running fire department display, runs December 1–31 (closed Christmas) at 307 Gay St., Cambridge, MD. Hours: Mon–Fri 6–9 PM; Sat–Sun 1–4 PM and 6–9 PM.

The Nutcracker: Eastern Shore Dance Academy presents “The Nutcracker” at Cambridge South Dorchester High School on December 14 at 11 AM and 4 PM. Tickets are available in advance at ESDA or at the door.

Frosty’s Holiday Village: Join For All Seasons for an evening with Frosty on Friday, December 6, 2024, from 5–8 PM at Anchor Church in Easton. Enjoy free holiday fun, including professional photos with Frosty, crafts, cocoa, cider, winter treats, and a showing of Frosty’s Winter Wonderland on the big screen.

Local Parades

Delight in festive holiday parades hosted by nearby towns.

November 29, 2024
 

Chestertown Parade

6-8 PM at Fountain Park

November 29, 2024
December 5, 2024
 

Denton Parade

6 PM in Historic Downtown Denton

December 5, 2024
December 5, 2024
 

Berlin Parade

7 PM on S Main Street

December 5, 2024
December 6, 2024
 

Centreville Parade

6:30 PM in Downtown Centreville

December 6, 2024
December 7, 2024
 

Easton Parade

6:30 PM in Downtown Easton

December 7, 2024
December 7, 2024
 

Cambridge Parade

5 PM in Downtown Cambridge

December 7, 2024
December 7, 2024
 

Ocean City Parade

11 AM from Old Landing Rd to 120th St

December 7, 2024
December 7, 2024
 

Rock Hall Parade

6 PM on Main Street

December 7, 2024
December 8, 2024
 

Salisbury Parade

1-3 PM on Mt. Hermon Rd and E Main St

December 8, 2024
December 14, 2024
 

St. Michaels

10:30 AM on Talbot Street 6 PM Boat Parade on St. Michaels Harbor

December 14, 2024
December 14, 2024
 

Hurlock

12-1 PM on Main Street

December 14, 2024
 

Holiday Dining or Carryout

If you’re skipping the kitchen this year, check out these local spots for a delicious dine-in or carryout holiday feast.

Hunter’s Tavern –101 E Dover St, Easton, MD

Knoxie’s Table – 180 Pier 1 Rd, Stevensville, MD

Suicide Bridge Restaurant – 6304 Suicide Bridge Rd, Hurlock, MD

Deep Blue – 14028 Augustine Herman Hwy, Galena, MD

Caroline Culinary Arts – 512 Franklin St, Denton, MD

Hyatt Regency – 100 Heron Blvd, Cambridge, MD

Amish Market – 101 Marlboro Ave, Easton, MD

Village Shoppe – 501 S Talbot St, St. Michaels, MD

Piazza Italian Market – 218 N Washington St, Easton, MD

NYE Celebrations

Ring in the New Year with local ball drops, festive events, and celebratory dinners on December 31st!

New Year’s Eve Celebration

Celebrate New Year’s Eve in Downtown Salisbury with live entertainment, activities, and local food!

First Night Talbot

Downtown Easton offers the Blue Crab Drop and free family fun!

New Year’s Eve Dinner

Special New Year’s Eve dinner at The Kitchen at the Imperial in Chestertown.

Rock Kent

Ring in the New Year at Kent Island Resort with The Nowhere Men.

Bistro New Year’s Eve Dinner

Enjoy a 5-course prix fixe menu this New Year’s Eve at the Bistro in St. Michaels.

4:30 PM – 9 PM

Peace, Love, and New Year’s Cheer

Ring in the New Year 60’s style at the Cow Barn in Ridgely with DJ Jason, Chef Kneller, and cocktails!

New Year's Eve on the Island

Celebrate New Year’s Eve at Fager’s Island with DJs, champagne, VIP access, and a photo booth!

New Year's Eve Celebration

Celebrate in Berlin with a 6 PM ball drop, music, and fun for all ages—free to attend!

NYE Pot Luck Supper

Bring a dish to share and enjoy live music by Joe Holt at The Mainstay in Rock Hall!

New Year’s Eve Celebration

Celebrate New Year’s Eve in Downtown Salisbury with live entertainment, activities, and local food!

Follow Us On Instagram