There’s something about visiting and living in Dorchester County here in the Heart of the Chesapeake, with its small town flavor, that just makes the holidays more joyful. Experience it for yourself at one of our holiday events, in our independently owned shops and galleries brimming with interesting gifts, and in our restaurants, with warm-your-belly seafood and friendly faces. Plus you can taken advantage of off-season rates at the hotels and B&Bs! And don’t miss the Crab Basket Tree — made entirely of the traditional baskets watermen use to harvest crabs — it earned Cambridge a spot on the list of “Top 12 Christmas Towns in Maryland”! Make it a Maryland Eastern Shore holiday season — and enjoy!

If you prefer to see a chronological listing of events, see our full calendar.

(Photo of the Crab Basket Tree in Cambridge above by Jill Jasuta Photography.)


Christmas Train Garden in Cambridge, MD


Nativity Display

Nov. 26-Jan. 3: On Wednesdays and Sundays throughout the holiday season, see more than 25 nativity scenes from around the world on display at Cambridge House Bed & Breakfast. Reservations required. MORE

Christmas Train Garden

Dec. 2-30: Volunteers with the Cambridge Rescue and Fire Company spend weeks building this train garden, a wonderful tradition for more than 80 years. New set-up this year! MORE

Festival of Wreaths Gala

Dec. 7: Gala for the Festival of Wreaths featuring handcrafted wreaths, live music, refreshments, auction, and more. The silent auction for the wreaths ends at the Dec. 7 event, but you can view and bid on them before the event. Proceeds benefit Pleasant Day Adult Medical Day Care. MORE

Holiday Home Tour

Dec. 10: See historic Dorchester County homes and other sites dressed up for the holidays. MORE

Luminaria Night Celebration in Vienna

Dec. 16: Glowing luminarias line the streets of Vienna, a 300-year-old small town on the banks of the Nanticoke River. Historic homes and churches open their doors for tours, music, refreshments, and old-fashioned hospitality.  MORE

Cambridge Dorchester Christmas Parade


Crab Basket Tree Lighting

Dec. 2: Celebrate the holiday season Dorchester-style with the lighting of the Crab Basket Christmas Tree, built by local volunteers out of bushel baskets used by watermen for harvesting crab. The lighting happens around 4:45pm, just before the Christmas Parade kicks off at 5pm on Dec. 2. MORE

Cambridge Dorchester Christmas Parade

Dec. 2: Marching bands, floats, classic cars, horses, and more fill the streets of downtown Cambridge during this nighttime Christmas parade — one of the largest on the Eastern Shore. More than 90 parade entries! Begins at 5pm. MORE

Free Holiday Movies

Dec. 2-24: Cambridge Premier Cinemas hosts Free Holiday Movies in December! All show times are at 10am. See the schedule.

Bloodys and a Christmas Movie

Dec. 3: The Wine Bar hosts a showing of the 1947 holiday classic movie, “The Bishop’s Wife,” during their Bloody Mary bar event. MORE

Hurlock Christmas Parade & Celebration

Dec. 9:  Begins at 6pm. Festivities include cookies with Santa, tree lighting and more. The theme of this year’s parade is “Polar Express.”  MORE

Second Saturday and Art Walk – Holiday Edition

Dec. 9: Downtown Cambridge rolls out the holly jolly red carpet for Second Saturday. Meet Santa from 5 to 8pm at 447 Gallery, with children’s activities, live music, and more. Carriage rides, pop-up carolers, specials in the shops and galleries, and a festive Art Walk are part of the fun, too. Also Cambridge Main Street will do a drawing for the winner of the Shop, Dine & Win Promotion. (Shop and dine with participating downtown businesses, be entered to win one of several prizes). MORE

Santa Swim

Dec. 9: Volunteers take a dip in the chilly waters of the Choptank River to raise money for local families in need. At the Hyatt Chesapeake. Each participant gets a Santa hat. MORE

Christmas Cookie Walk

Dec. 9: Stroll through a collection of more than 1,000 delicious, homemade cookies, and for $10 per box, pick and choose to fill your own box. Supports Habitat for Humanity Choptank’s senior repair program in Cambridge. MORE

New Year’s Eve Boat Drop

Dec. 31: Join in the celebration in Downtown Cambridge as folks gather to watch a small replica waterman’s boat whizz down 60 feet of track to bring in the new year. MORE


The Nutcracker by Eastern Shore Dance Academy


Jazz in the Sanctuary

Dec. 3: Waugh Chapel hosts the Jazz in the Sanctuary Band, an afternoon of gospel-inspired jazz and holiday songs. MORE

A Christmas JuBELLee

Dec. 3: The Bells of the Bay handbell choir performs traditional Christmas carols and a range of Christmas songs. MORE

Praise and Christmas Concert

Dec. 3: The St. Paul’s United Methodist Church Praise Team invites everyone to join in an evening of special praise and worship and a celebration of the Christmas season in song. MORE

Holiday Concerts with Chorus of Dorchester

Dec. 8, 12: The Chorus of Dorchester presents free holiday concerts. The December 8 performance happens at historic Christ Episcopal Church in Cambridge; the December 12 performance is at the Dorchester Center for the Arts in Cambridge. Free, but seating is limited. MORE

Christmas Choral Concert with Tidewater Singers

Dec. 10: The Tidewater Singers present a holiday concert at the historic Christ Episcopal Church in Cambridge. MORE

Karaoke Happy Hour Christmas Edition

Dec. 8: Layton’s Chance Vineyard and Winery hosts a special Christmas edition of Karaoke Happy Hour with a Christmas carol karaoke contest; plus prizes awarded for best ugly sweaters. MORE

A Christmas JuBELLee

Dec. 14: The Bells of the Bay handbell choir performs traditional Christmas carols and a range of Christmas songs in Woolford. MORE

Bluegrass Nutcracker

Dec. 15: Dreading another season of canned Christmas music? Get in the holiday spirit with a fresh take on Tchaikovsky’s Christmas classic with Front Porch Orchestra performing a bluegrass-steeped rendition of the Nutcracker at 447 Gallery. MORE

Christmas Carol Sing-Along

Dec. 16: Be a part of the Christmas Carol Sing-Along with Anna Burgess at Canvasback Restaurant and Coolahan’s Irish Pub in Cambridge. MORE

“The Nutcracker” by Eastern Shore Dance Academy

Dec. 16 and 17: Dancers with the Eastern Shore Dance Academy perform the holiday classic. MORE

There Might Be No Christmas

Dec. 16: Dinner Theater at St. Paul’s United Methodist Church. Santa has called everyone to gather because they are under suspicion of theft! One of the helpers is responsible, and the group needs to find out who. Bring your family and friends and enjoy a night out filled with laughter and joy! MORE


Mistletoe & Mimosas

Dec. 2: Join Layton’s Chance Winery for wreath making… and mimosas! MORE

Eat, Drink, and Make Charms

Dec. 7: Join Jewelry By Cottage Studio and the Wine Bar for an evening of wine tasting and delicious hors d’oeuvres. And create and take home six wine glass charms. Space is limited; must reserve ahead. MORE

Holiday Greeting Cards and Gift Tags Workshop

Dec. 9: Use stamps, paper, ribbon, glitter and more to make beautiful and fun cards and tags for the holidays at this Dorchester Center for the Arts workshop. Kid and adult friendly.Free; reservations suggested. MORE

Holiday Desserts Baking Demo

Dec. 10: Bistro Poplar’s pastry chef shares her top tips and secrets for making traditional holiday treats. Tastings included. Always a sell-out — reserve ahead. MORE

Paint Date at the Wine Bar

Dec. 17: Paint a cardinal in the snow for a touch of holiday flair. No experience needed; they’ll walk you through each step and you’ll go home with a finished painting. At the Wine Bar. MORE


Hurlock Christmas Parade, photo by Chris Watson of Shore Impressions


Holiday Market on the Farm

Dec. 1-3: Breckenridge Farms hosts a weekend of shopping, entertainment, and mingling. plus fresh-cut Fraser Christmas trees for sales and vendors selling their wares. Santa will be there Dec. 2,  10:30-11:30am and 3-4pm and Dec. 3, 11am-1pm.  You can also write letters to Santa all weekend long. MORE

Maryland Antiques Christmas Open House

Dec. 2: Enjoy a wide selection of uniques and antiques offered by several vendors — and Santa will be there in the evening hours.

Breakfast with Santa

Dec. 2: St. Luke’s United Methodist Church hosts breakfast with Santa. Pictures with Santa, plus arts and craft activities. MORE

Santa at Mowbray’s Garden Center

Dec. 2: Bring the little ones out to visit with Santa in Mowbray’s sleigh and tree forest from 10 to 11:30am. While you’re there, check out their Christmas trees and fresh garlands and wreaths.

Simmons Center Market Open House

Dec. 2: Family owned for 80 years, Simmons hosts an open house with tastes of fresh-ground sausage, fresh-baked cookies, and more. Plus poinsettias and garlands and more available for purchase. MORE

Christmas Open House at Mowbray’s Garden Center

Dec. 3: Pick out your Christmas tree, visit with Santa, check out the vendors, crafts for kids, and face painting. Santa will be on hand for visits from 10am to 12pm.  (If you miss Santa, he will be in his workshop every Saturday until Christmas!)

DCTC Greenhouse Holiday Open House

Dec. 8: See handcrafted holiday arrangements and crafts created by students at DCTC (Dorchester Career & Technology Center) Greenhouse; can be purchased that day or pre-ordered for later pickup. MORE

Country Chics Holiday Open House

Dec. 9: Door prizes on the hour, pop-up specials, and the first 20 people through the door receive a snowman ornament. In Hurlock. MORE

Second Saturday – Holiday Edition

Dec. 9: Meet Santa from 5 to 8pm at 447 Gallery in downtown Cambridge, with children’s activities, live music, and more. MORE

Santa at Mowbray’s Garden Center

Dec. 9: Bring the little ones out to visit with Santa in Mowbray’s sleigh and tree forest. While you’re there, check out their Christmas trees and fresh garlands and wreaths. MORE

Breakfast with Santa & Mrs. Claus

Dec. 10: Enjoy breakfast with Santa and Mrs. Claus at the East New Market Fire Co. MORE

WHCP Santa Hotline

Leave a message for Santa on WHCP Radio’s Santa Hotline and let him know what you’re dreaming of for Christmas — for children of all ages! Call 443-637-6001. Tune in to 101.5 FM and listen for the best greetings starting Dec. 11.


 Wreaths Across America - Eastern Shore Veterans Cemetery


Dorchester Santa Toy Drive Finale

Dec. 9: The Dorchester Santa Toy Drive is happening this holiday season — bring a new, unwrapped toy to a participating merchant throughout Dorchester County. The finale is Dec. 9 at RAR Brewing. MORE

Wreaths Across America

Dec. 16: Help place wreaths on veterans’ gravestones at the Eastern Shore Veterans Cemetery, in coordination with wreath-laying ceremonies at Arlington National Cemeteries and 1,100 other locations all over the country and beyond. Donations and volunteers welcome. MORE



New  Year’s Eve Yoga Party

Dec. 31: Get ready for a healthy and relaxed new year with opportunities for yoga all day with Anahata Yoga. MORE

New Year’s Eve Boat Drop

Dec. 31: Join in the celebration in Downtown Cambridge as folks gather to watch a small replica waterman’s boat woosh down 60 feet of track to bring in the new year. MORE


Do you know of other holiday events happening in Dorchester County, Maryland, that should be added to this list? Let us know! Email them to


“Cambridge’s crabby bushel basket tree will have you both drooling, and smiling from ear to ear.”
— Only in Your State

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