The holiday season is upon us, and for those of us lucky enough to live on the Eastern Shore, that means we have a fantastic selection of activities to help us get into the spirit.  In this month’s blog post, we’ve compiled a list of some of our favorite family-friendly events taking place across the peninsula so you can fill your weekends with holiday cheer.

November 16-December 31: Winter Wonderfest at Hudson Fields | Milton, DE

Christmas tree with people celebrating outside at WonderFest

Ring in the season at this month-and-a-half-long festival that includes an ice skating rink, a 1.5-mile drive-through Lights Spectacular, hayrides, and a Christmas village complete with carnival rides, games, a Christmas tree farm, food trucks, craft vendors, and Santa’s Workshop. Opening day kicks off on November 16 with a 5k Run/Walk and one-mile Fun Walk through the lights display (you can pre-register online). Feel extra warm and cozy knowing that proceeds from Wonderfest go to local charities; since 2016, the festival has raised over $140,000 for local non-profits! For dates, hours and discounted tickets, visit the festival’s website.

November 29: Berlin Tree Lighting & Holiday Open House | Berlin, MD

Horse and carriage at Christmastime

Looking to entertain visiting family members Thanksgiving weekend? What could be more perfect than a tree lighting festival in one of America’s favorite small towns?! Stroll the decorated streets and shops, enjoy local artists and musicians, and go for a carriage ride with Jolly Old St. Nicholas himself. Be sure to stop by Stevenson UMC for some holiday caroling before winding your way to the Calvin B. Taylor Museum for a candlelit tour. Activities last from 5:30PM to 9PM, with a 6PM tree lighting in front of the Atlantic Hotel. See Berlin Main Street’s website for more details.

December 4-8: Winter Wonderland Music & Tree Festival at Sailwinds Park | Cambridge, MD 

Winter Wonderland festivities begin Wednesday afternoon with a senior dinner (55+) and continue into the weekend with a Friday night holiday dance (adults only) and a family-friendly open house at Governor’s Hall that features a Festival of Trees, visits with Santa, live music, a craft show, and food and beverages. Proceeds benefit the Leukemia and Lymphoma Society of the Eastern Shore and a local family. For more information, visit the event’s facebook page.

December 6-8: Christmas in Easton | Easton, MD

Santa and Mrs. Claus waiving hello from a firetruck in downtown Easton, MD

Easton offers an abundance of holiday events throughout November and December, but this particular weekend offers the most bang for your buck! The weekend starts with Moonlight Madness on Friday, December 6 from 4-10PM. Enjoy music in the streets, pictures with Santa, special in-store events, and giveaways totalling over $10,000! The fun continues on Saturday with the annual tree lighting in Thompson Park at 6PM, followed by a holiday parade complete with holiday floats, classic cars, bands, and more. Don’t forget to wind your way over to the Waterfowl Building, where the third annual Arts & Crafts Marketplace will feature fine art and crafts from regional artisans all weekend long. For a complete list of activities, visit the Discover Easton website.

December 12-15: Christmas in St. Michaels | St. Michaels, MD

Horse drawn carriage with Christmas carol singers

We couldn’t leave this oldie-but-goodie off the list! Christmas in St. Michaels is back for its 33rd year, celebrating with historic home tours, a gingerbread house competition, the holiday Marketplace & Sweet Shoppe, Santa’s Wonderland, and the Saturday-morning Talbot Street Parade, which kicks off this year with a one-mile Santa Dash fun run. Grab your Santa hats and join the festivities! View a complete list of activities here at the Christmas in St. Michaels website

December 14: Salisbury Zoo’s Critter Christmas | Salisbury, MD

Santa and Mrs. Claus will be setting up shop at the Salisbury Zoo for one day, and they’re looking for some creative little helpers to work on over a dozen holiday craft projects! Bring the kids for a fun-filled day of crafting and peruse an assortment of local artisan booths for last-minute holiday gifts. Don’t forget to visit all the animals to wish them Happy Holidays! Visit the Zoo’s website for more info. 

We hope you have an opportunity to enjoy at least one of these great events! Let us know what you think, and feel free to add to our list with your favorite local festivities. However you celebrate, we wish you and your family a happy holiday season!