Whether you’re decking the halls, getting crafty, or checking in with Santa … there’s something extra special about Christmas in the Heart of Chesapeake Country. From the Crab Basket Tree and Christmas parades to musical performances, make it a Maryland Eastern Shore holiday season in 2019! We’ve compiled more than 40 of the big holiday events and happenings. For details, just click on the event name. We’ll be adding to this listing as we find out about more events.

And, if you’re looking for a place to curl up and relax – or need room for visiting friends and family – take advantage of off-season rates at hotels and B&Bs! See our lodging listings.

Events Calendar

Ongoing Seasonal Attractions

Crab Basket Christmas Tree  – Cambridge’s Crab Basket Tree has become one of the Shore’s favorite holiday destinations for family photos! Gather round the tree for selfies or just to admire. The tree is constructed by volunteers of nearly 200 crab baskets that were used by watermen for crabbing.  Located in the Craig’s Drug Store parking lot, Race and Gay Streets in Cambridge, MD.

Christmas Train Garden – Check out Cambridge’s train display downtown every day in December. For 85 years, volunteers with the Cambridge Rescue Fire Company have created this spectacular train garden for the holidays. Sneak peek Nov. 30 right after the Tree Lighting (see above). Open daily, Dec. 1-31, Mon-Fri, 6-9pm and Sat & Sun 1-4pm and 6-9 pm. Free (monetary donation or canned food donation welcome).

Nativity Scenes from Around the World – At Cambridge House Bed & Breakfast. Wednesdays and Sundays through the holiday season. Reserve in advance.

Free Holiday Movies – Cambridge Premier Cinemas hosts a FREE Holiday Movie Series starting Nov. 30.  Movies start at 10am.


Ho-Ho-Holiday Fun, Santa Sightings & Festive Lights

Christmas Open House at Mowbray’s Garden Center – Pick out your Christmas tree, visit with Santa from 10am-12pm or browse the holiday gift shop at Mowbray’s holiday winterland Nov. 30, 9am-5pm.

Santa at Maiden Maryland – Santa will be at Maiden Maryland on Nov. 30 from 5 to 6pmish, and then again with Mrs. Claus on Dec. 21 (time to be announced).

A Cambridge ChristmasA Cambridge Christmas – Ring in the holidays Thanksgiving weekend at the Christmas Tree Lighting at Spring Valley at the Court House at 5:30pm on November 30.  Live music and refreshments. 206 High St., Cambridge.

Santa at Cabin Fever Play Centre – Dec. 1 from 1 to 3pm with regular admission.

Spaghetti with Santa – Enjoy all-you-can-eat spaghetti plus a visit with the Santa on Dec. 4 from 5pm to 7:30pm, hosted by the Dorchester County Technology and Career Center. Santa, Mrs. Claus and elves, as well as games, crafts, cookie decorating.

Cambridge-Dorchester Christmas Parade – Be dazzled by light, sound and sights of one of Maryland’s largest nighttime parades starting at 5pm on Saturday, Dec. 7. Celebrate Christmas Past and Present as marching bands, floats, classic cars, horses and Santa fill Downtown Cambridge’s streets for this beloved holiday happening!

Holiday Home Tour – Enjoy tours of six homes in Cambridge and East New Market in this annual tour hosted by the Cambridge Woman’s Club on Dec. 8.

Festival of Wreaths – Pleasant Day’s 20th annual Holiday Benefit Gala and Festival of Wreaths is December 5 in Cambridge. Doors open at 5:30pm. Handcrafted wreaths, entertainment, refreshments, and more. The silent auction of wreaths has been up and running since Nov. 14, so you can stop by before Dec. 5 to browse and make bids.

Ugly Christmas Sweater Karaoke – Prizes awarded for best ugly sweaters! At Layton’s Chance Winery, 7-10pm on Dec. 6.

Winter Wonderland Music and Tree Festival – Enjoy a magical winter wonderland with festively decorated trees. Includes dance on Dec. 6 and live music, tree auction, and pics with Santa on Dec. 8. At the Elks Lodge.

Christmas Open House at Windy Way Horses – Pony rides, carriage rides, Christmas crafts, vendors. Plus meet the animals! 12-4pm on Dec. 7 at the farm in Hurlock.

Breakfast with Santa in East New Market – All-you-can-eat feast with Santa at the East New Market Fire Company, 7am-10am on Dec. 8. $10 per person; $5 for those under 12.

Santa Swim – Volunteers take a chilly dip in the Choptank River for charity. Take part or just watch! Dec. 14 at the Hyatt Chesapeake.

Breakfast with Santa at Denny’s – Enjoy breakfast, take pics with Santa, and 20 percent of proceeds goes to Pleasant Day Medical Adult Care. From 9am to 12pm on Dec. 14.

Festival of Trees in Hurlock– Admire the decorated trees and bid on them with a chance of taking them home. At the Hurlock Volunteer Fire Company on December 14-15.

Christmas Lights on the Choptank Boat Parade – Boaters: deck your hulls and take part in the second annual lighted boat parade along thee Choptank River and Cambridge Creek! Spectators, bundle up and enjoy the show! Line-up of boats at 4:45pm; parade begins 5 or 5:15pm on December 14.

Hurlock Christmas Parade – Begins at 5pm on December 14.

Holiday Second Saturday – Downtown Cambridge shops will be open late Dec. 14 during this special holiday edition of Second Saturday. Art Walk. Winners of the Shop & Dine Promotion.

Christmas Cookie Wine Pairing – Head to Layton’s Chance Winery for tasty pairings of Christmas cookies with wines. 12-5pm on Dec. 15.

Cookies & Cocoa with Santa in Secretary – Kids can visit with Santa, decorate cookies, and have hot cocoa and firetruck rides through town on Dec. 15 from 1 to 3pm.

Santa at Mowbray’s Garden Center – Visit with Santa from 10am to 12pm at Mowbray’s Garden Center in Cambridge.

Santa & Mrs. Clause at Maiden Maryland – Santa and Mrs. Clause take a break from their busy schedules for some ice cream at Maiden Maryland on Dec. 21. Time to be announced.

Luminaria Night Celebration – Glowing luminarias line the streets of historic Vienna Dec. 21, 5 to 8pm, for this treasured holiday tradition. Historic homes and churches open their doors for tours, music, refreshments, and old-fashioned hospitality. Free. Tickets cost $5 for home tours.

Music & Performances

Bluegrass Nutcracker at 447Holiday Concerts with Chorus of Dorchester – Free holiday concert at 7pm on Dec. 13 at Christ Episcopal Church in Cambridge and then on Dec. 17 at 7pm at the Dorchester Center for the Arts.

The Nutcracker – The Eastern Shore Dance Academy presents “The Nutcracker” at 6pm on Dec. 14 and 3pm Dec. 15 at Cambridge-South Dorchester High School in Cambridge.

Christmas Choral Concert – The Christ Church Concert Series features a Christmas Choral Concert with the Tidewater Singers on Sunday, Dec. 15 at 4pm. $10 for adults/free for students. Reception follows in the parish hall.

Bluegrass Nutcracker – Dreading another season of canned Christmas music? Get in the spirit with a sizzling, bluegrass-steeped bar-for-bar rendition of Tchaikovsky’s Christmas classic with Front Porch Orchestra on Friday, Dec. 20 at 447 Gallery in downtown Cambridge.

Holiday Crafting and Creating

Wreath makingMany of these workshops will sell out, so reserve your spot as soon as you can!

Fresh Wreath Making Class – At the East New Market Volunteer Fire Company on Dec. 1.  Must pre-register by Nov. 29.

Fresh Greens Holiday Wreath Workshop – At the Blue Awning on Dec. 4. Must reserve in advance.

Make Your Own Soap at Blue Ruin – Learn from Simon Babycat Co. and create your own personalized photo soap and more on  Dec. 4 at Blue Ruin cocktail lounge.

Wine & Design – Enjoy a morning of wreath making and bottomless mimosas on Dec. 8 at Layton’s Chance Winery.

Holiday Treats Demo at Bistro Poplar – Join pastry chef Emily Salisbury for this annual tradition on Dec. 8.

Wreath Making Fundraiser – For the South Dorchester School 8th grade class. Dec. 7 at Mowbray’s Garden Center.

Fresh Greens in a Decorative Bucket Workshop – At the Blue Awning on Dec. 11 at 5:30pm. Must reserve in advance.

Candy House Decorating Workshop – All ages can experience the fun of building these holiday houses at the Dorchester Center for the Arts on Dec. 14. Two workshops to choose from.

Christmas Centerpiece Design Class at Florals Unique – Learn to create your own Christmas centerpiece from a master florist at Florals Unique on Dec. 19 at 7pm. Must register in advance.

Shopping and Unique Gifts

Gallery of Gifts at DCAGallery of Gifts at Dorchester Center for the Arts – See small works of art created by local artisans that make wonderful gifts at the DCA now through Dec. 24. Meet the artists at a free reception 5-7:30pm on Dec. 14. This year the show follows the theme “Water Moves Us” complementing the Smithsonian Water|Ways exhibition.

Main Street Gallery – Browse distinctive works of art from local artists at this gallery in Downtown Cambridge now through December.

Pop-Up Shop at Mirror Mirror Salon – Gifts, stocking stuffers; many items under $10. Featuring local authors, jewelers, and more. Open Tues.-Sat. through Dec. 28. 443 Race St., Cambridge.

Small Business Saturday – Share your love for small local independent brick and mortar businesses this holiday season during this nationwide event on the Saturday after Thanksgiving, Nov. 30.

Mistletoe Market – See the vendors set up in Downtown Cambridge’s Cannery Way on Saturday, Nov. 30, Dec. 7, and Dec. 14, 11am-4pm.

Simmons Market Holiday Open House – Sample tastes of the goodies they’ll be offering for the holidays from 9am to 3pm on Dec. 7.

Christmas Open House at Bay Country Shop – They’ll have 20% off all apparel on Dec. 14. Plus free goodie bags to the first 10 people who spend $100. Vendors, book signing, floral arrangements, and more.

Giving Thanks & Giving Back

Wreaths Across America - Eastern Shore Veterans CemeteryDorchester Santa Toy Drive – Donate a new toy for a local child in need. There are several drop-off locations at businesses; check the Dorchester Santa Toy Drive Facebook page for the latest. The drive ends Dec. 14 with a festive finale at RAR Brewing from 12pm until closing time.

Wreaths Across America – Help place wreaths on the gravestones of veterans at the Eastern Shore Veterans Cemetery on Dec. 14.


New Year’s Eve & New Year’s Day

New Year’s Eve Ball Drop for Kids at Cabin Fever Play Centre – The ball drops at 5pm so you don’t have to stay up until midnight! Dec. 31 from 3 to 6pm.

New Year’s Eve Boat Drop – Downtown Cambridge hosts a New Year’s Eve Boat Drop with a small replica of a deadrise — the traditional waterman’s workboat — dropping TWO times: once at 8pm for the kids and early risers, and then again at midnight on Dec. 31 to bring in the New Year. 300 block of Gay Street next to the Crab Basket Tree.

First Day Hike – Join a “First Day Hike” with the Harriet Tubman Underground Railroad State Park & Visitor Center  at 10am. The walk goes through part of Blackwater National Wildlife Refuge. Reservations required. Visitor Center will be open until 5pm and hot drinks and light snacks will be served.

Find details on all these happenings on our online calendar!

Events Calendar

Print Friendly, PDF & Email