Whether you’re decking the halls, getting crafty, or checking in with Santa … there’s something extra special about the holidays in the Heart of Chesapeake Country. Dorchester County is home to independent shops with great gift ideas and friendly shopkeepers, intriguing art galleries, and excellent restaurants offering indoor, outdoor and take-out dining. No wonder Cambridge was named one of the “Top 12 Christmas Towns” by Only in Your State for 2021!

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.

Where to Stay

Ongoing Seasonal Attractions

Crab Basket Christmas Trees  – Dorchester County is now home to two Christmas trees built out of bushel baskets used for crabbing (crabs are big around here)! First, there’s Cambridge’s Crab Basket Tree, a tradition that began seven years ago and has become one of the Shore’s favorite holiday destinations! 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. It’s usually up by the weekend after Thanksgiving. A more recent addition is the Crab Basket Tree in Vienna, MD. Now in its second year, it will be created from some 150 bushel baskets. The official lighting of the tree is part of Vienna’s Christmas Parade festivities on Nov. 27.

Christmas Train Garden, Cambridge, MDChristmas Train Garden – For 87 years, volunteers with the Cambridge Rescue Fire Company have created this spectacular train garden for the holidays. The RFC Train Garden is the longest continually operating fire department train display in the nation! This year’s themes include “Train Gardens of the Past” and the “Harvesters at the Holidays” display honoring Dorchester County’s heritage of bountiful seafood and farming production. Free admission, but donations are welcome. The display is open for inside viewing throughout December: Monday through Friday, 6-9pm and Saturday and Sunday 1-4pm and 6-9pm. Closed Christmas Day. Best to check their Facebook page before visiting for any last-minute updates. 307 Gay St., Cambridge, MD.


Shopping and Unique Gifts

Dorchester County is all about great indie (independently owned) shops. Antiques, vintage, upcycled furniture, artist and artisan-created works of all kinds, fine jewelry, Eastern Shore and Maryland-themed items, toys and clothes for the wee ones, women’s apparel and accessories, home and garden decor, and more! All with the attention and friendliness of shop owners. See our listing of shops.

Where to Shop

Earrings by Linda Starling at Main Street Gallery, Cambridge, MD

Gallery of Gifts at Dorchester Center for the Arts – This seasonal favorite features an extensive selection of handcrafted items from local and regional artists, perfect for thoughtful gift-giving. You’ll find fiber art, gold and silver jewelry, glass, photography, paintings, and ceramics. Show runs Nov. 5 through Dec. 23.

‘Bright and Beautiful’ at Main Street Gallery – Browse distinctive works of art from local artists at this gallery in Downtown Cambridge now through December. The show is “Bright and Beautiful,” and features smaller works of art for gift giving. The show runs Nov. 4 through Jan. 2.

Holiday Events


Bushel Basket Tree in Vienna, MD - Photo by Ellen Wheatley

Nativity Scenes From Around the World
2-5pm, Wednesdays and Sundays, Dec. 1-Jan. 5
Cambridge House Bed & Breakfast hosts a display of Nativity scenes from around the world. $10 per person; reserve at 410-221-7700.

Holiday Concerts with Chorus of Dorchester
The all-volunteer, 60-voice Chorus of Dorchester performs three free holiday concerts with the music of Bach, Handel, Dvorak, Mozart and more:

  • December 2, 11am at the Hyatt Regency Chesapeake Bay Resort, 100 Heron Blvd., Cambridge
  • December 11, 4pm at Christ Episcopal Church, 601 Church St., Cambridge
  • December 14, 7pm at Dorchester Center for the Arts, 321 High St., Cambridge

Merry & Bright Nights at Mandala Pies
December 3, 10, 17, 22 and 23; 6-8pm
Mrs. Claus visits the bakery  to do crafts with children. Cocoa and treats, too! Free! Pie will be available for purchase.

Ugly Christmas Sweater Party at Layton’s Chance Winery
December 3, 6-9pm
Games and prizes for the best ugly Christmas sweaters!

Christmas Open House at Simmons Center Market
December 4
Stop by this classic, family-owned market and gift shop for free samples and more. Lots of seasonal items, from classic candy to fresh wreaths to gifts.

Santa at Mowbray’s Garden Center
December 4, 11, 18
Visit with Santa from 10am to 12pm at Mowbray’s Garden Center, where they also have trees and lots of holiday items.

Hot Chocolate with Santa
December 4
Join the big guy for hot chocolate at Go! Wash Car Wash in Cambridge, 1-4pm

Cambridge Dorchester Christmas ParadeCambridge-Dorchester Christmas Parade
December 4
Be dazzled by light, sound and sights of one of Maryland’s largest nighttime parades starting at 5pm. The 2021 theme is “Fishing You a Merry Christmas.” 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 Cookie Exchange & Craft Market
December 11, 11am-3pm
Emily’s Produce hosts a “no baking, just taking” cookie exchange. Craft market that day, too.

Hurlock Vol. Fire Co. Festival of Trees
December 11, 11am-4pm
See the decorated trees, 11-1pm; auction of trees is 1-3pm. Also Cookies with Santa from 3-4pm.

Winter Fair
December 11, 12-4pm
The Unity-Washington United Methodist Church hosts the Winter Fair with craft and vendor tables and food and drink.

Christmas on Pine
December 11, 1-7pm
Groove City Black Heritage and Culture Group presents Christmas on Pine with Christmas caroling, Santa Claus, Christmas music, vendors, raffle and gift baskets, s’mores, and more.

Wreath Making at Mowbray’s Garden Center
December 11, 4-6pm
Make a wreath with fresh greens at Mowbray’s Garden Center. Benefits Dorchester Youth Lacrosse.

Hurlock Christmas Parade
December 11, 5pm
This year’s theme is “Tis the Season for Joy.” Begins at 5pm.

Christmas on the Choptank Boat Parade, Cambridge, MDChristmas Lights on the Choptank Boat Parade
December 11, 5pm
Deck the hulls with this boat parade on Cambridge Creek. Begins around 5pm.

Cambridge Christmas Tree Lighting
December 11, 5-6pm
New date this year! Join in as the tree at Spring Valley is officially lit. Santa will be available for photos.

Christmas Carol Trivia
December 14, 7pm
Blue Ruin hosts Christmas Carol Themed Trivia with Chuckie Hayward. Karaoke follows at 9pm, and Christmas carols are welcome.

The Nutcracker Ballet
December 18
The Eastern Shore Dance Academy presents the Nutcracker at 12pm and 5pm in the ballroom at the Hyatt Regency Chesapeake Bay Resort in Cambridge. Tickets will go on sale in early December.

Luminary Celebration in Vienna
December 18, 5-8pm
1,500 luminaria line the streets of the charming, historic waterfront town of Vienna. Plus historic house tours, Santa House, s’mores, and more.


Pick out the perfect tree at Mowbray’s Garden Center, Emily’s Produce (Emily’s offers both in person and delivery), with Mike Diaz (located behind the Dairy Queen), all in Cambridge. Or M&R Christmas Tree Farm in Hurlock. You’ll  also find live wreaths, garlands, poinsettias, and more at Mowbray’s and Emily’s, as well as at Simmons Center Market in Cambridge.

Giving Thanks & Giving Back

Wreaths Across America - Eastern Shore Veterans Cemetery

Wreaths Across America – On December 18 at 10am, Wreaths Across America will be at Eastern Shore Veteran’s Cemetery to remember and honor our veterans through the laying of Remembrance wreaths on the graves of our country’s fallen heroes and the act of saying the name of each and every veteran aloud. Sponsor a wreath or help with the wreath laying.

Dorchester Santa Toy Drive
Donate a new toy for a local child in need. There will be several drop-off locations at businesses; check the Dorchester Santa Toy Drive Facebook page for the latest. The drive usually ends in mid-December with a festive finale at RAR Brewing.

Santa Swim 
Volunteers take a chilly dip in the Choptank River for charity. Take part or just watch! Dec. 11 at the Hyatt Regency Chesapeake Bay Resort in Cambridge. Find out more.

Salvation Army – Look for the iconic red kettles either set up outside of stores or smaller kettles on countertops inside shops. Donations help local families struggling with hunger, poverty, or job loss. Call 410-228-2442 x1008 for more info.

New Year’s Eve

More events to come as plans are announced!

New Year’s Eve in the Neck – Neck District Volunteer Fire Co. hosts a New Year’s Eve party Dec. 31 with appetizers, dinner, music, dancing, and a toast at midnight.

Find details on all these happenings on our online calendar!

Events Calendar


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