Catch that Eastern Shore holiday spirit!
Small-town charm, one-of-a-kind traditions, festive events, and friendly faces make the holidays special in Dorchester County! From the Crab Basket Christmas Tree and holiday train garden to parades, markets, and family fun, there's plenty to celebrate here in the Heart of the Chesapeake.
Make a getaway of it! Browse our independent shops and galleries, savor local seafood, and enjoy the beauty of our winter landscapes — including some spectacular birdwatching. Visiting friends or family? Check out our places to stay and make yourself at home.
Looking for holiday happenings? We've gathered events from across the county, with more being added throughout the season. Planning a holiday event in Dorchester County? Submit it to our events calendar so we can help spread the word.
JUMP TO:
🟥 Holiday Favorites All Season Long
🟥 Holiday Markets & Shopping
🟥 Parades, Performances & More
🟥 Holiday Crafts & Workshops
🟥 Giving Back
🟥 New Year's Events
Christmas Train Garden - Cambridge Rescue Fire Company - Photo by Jill Jasuta
Holiday Favorites All Season Long
The Original Crab Basket Christmas Tree
Only on the Eastern Shore! Nearly 200 authentic crab baskets, once used by local watermen, are stacked and decorated to create one of Cambridge's most beloved holiday traditions. Built by volunteers each year, this one-of-a-kind Christmas tree is a favorite spot for holiday photos. Find it at the corner of Race and Gay Streets in downtown Cambridge.
Christmas Train Garden
Thoughout December
All aboard for a holiday tradition more than 90 years in the making! Volunteers with the Cambridge Rescue Fire Company create an elaborate miniature world of towns, farms, forests, and holiday scenes, complete with model trains winding through it all. The display changes each year, so there's always something new to discover. At 307 Gay Street in Cambridge.
Ice Skating & Winter Village at Hyatt Regency Chesapeake Bay
Nov. 27, 2026–Feb. 14, 2027
Lace up your skates for winter fun at the Hyatt Regency Chesapeake Bay! The resort's seasonal synthetic ice rink and Winter Village bring a festive atmosphere to the waterfront, with skating, cozy fire pits, seasonal treats, and activities for the family. Skate rentals are available. Check the resort for this season's schedule and offerings.
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Bay Country Shop, Cambridge
Holiday Markets & Shopping
Skip the big-box stores and discover the charm of shopping small! Dorchester County's independently owned shops and galleries are filled with one-of-a-kind finds, from art, antiques, and handcrafted gifts to jewelry, clothing, home décor, and Eastern Shore treasures. And there's nothing quite like the friendly, personal touch of a local shopkeeper. Explore our local shops.
Throughout the season, holiday markets and special shopping events add even more festive fun. See all the upcoming markets and shopping events in our 2026 Holiday Events Calendar.
Mistletoe on Main: Cambridge Main Street's Shop 'Til You Drop promotion runs Nov. 14–Dec. 21, with raffle tickets earned for purchases at participating businesses.
SEE ALL HOLIDAY MARKETS & SHOPPING EVENTS
Christmas Dorchester Christmas Parade, Dec. 5 - Photo by Jill Jasuta
Parades, Performances & More
From sparkling holiday parades and visits with Santa to festive concerts, The Nutcracker, and holiday home tours, there's something for every age and interest. Gather your family and friends and make some holiday memories! Find all the fun events in our 2026 Holiday Events Calendar.
Wreath making at Simmons Center Market, Cambridge.
Holiday Crafts & Workshops
Get creative this holiday season! Make a handmade gift, craft a festive decoration, or simply enjoy trying something new. Local artists, businesses, and organizations offer workshops ranging from wreath-making and ornament decorating to all kinds of creative holiday projects. Many fill up quickly, so be sure to reserve your spot early! Find upcoming workshops and more in our 2026 Holiday Events Calendar.
New Year's Events
Check back for the latest!
And something to look forward to in January!
Cambridge Ice & Oyster Festival
January 15–16, 2027
The holiday fun doesn't have to end in December! Downtown Cambridge comes alive with dazzling ice sculptures, live carving demonstrations, family-friendly ice games, local oysters, music, fire pits, and more. This popular winter festival celebrates two Eastern Shore favorites — ice and oysters — with plenty of fun for all ages. Come for the incredible ice art, stay for the oysters and winter festivities! Find out more.
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