It’s another busy weekend locally as we continue with holiday events and activities across Delmarva, including SantaCon Ocean City, Christmas in St. Michaels, and the annual Diakonia Breakfast with Santa. Winterfest of Lights continues to dazzle in uptown Ocean City, while mid-town Ocean City businesses are banding together for a holiday block party and open house. First up, we’re headed to The Globe in Berlin for their Saddle Up Art Show. All that and more, right this way…

Saddle Up: Bicycle Art Show & Silent Auction

When: Thursday, December 10, 6pm-9pm

Where: The Globe, Berlin

What: The Eastern Shore International Mountain Bike Association is hosting an art show and silent auction at The Globe in Berlin this Thursday, December 10 to foster the ESIMBA’s mission to create, enhance and preserve the local trail opportunities across Delmarva. The artwork will stay on display until January 3rd.


When: Saturday, December 12

Where: Ocean City

What: It’s the 5th year for the annual SantaCon invasion in Ocean City, which means there will be plenty of Santas, elves, reindeer and more frolicking through town for the full-day event. Participants are also encouraged to bring donations for the Worcester County Humane Society.

Tea with Santa at Poplar Hill Mansion

When: Saturday, December 12, 1-4pm

Where: Poplar Hill Mansion, Salisbury

What: Mr. and Mrs. Claus will be at Poplar Hill Mansion in Salisbury this Saturday for their annual tea with Santa holiday tradition. Enjoy Christmas sweets, peppermint tea, holiday music, and pictures with Santa! Pictures are $5 per photo and will be mailed to you.

Christmas Train Garden

When: Saturday and Sunday afternoons in December; 1-4pm

Where: Pocomoke River Canoe Company

What: Enjoy the Corddry Company Crossing Train Garden this holiday season, a throwback to Snow Hill many years ago. Admission is free, however donations are welcome.

Winterfest of Lights

When: Thursday, November 19-Monday, January 3

Where: Northside Park, Ocean City

What: Hundreds of animated, lighted displays and over one million holiday lights will illuminate Northside Park in OCMD for the annual (and much beloved) Winterfest of Lights. This year’s holiday fun begins on Thursday, November 19 with the tree lighting and kickoff event. Winterfest of Lights is open on Sunday through Thursday from 5:30pm until 9:30pm, Friday and Saturday from 5:30pm until 10:30pm.

Cambridge Second Saturday

When: Saturday, December 12, 5pm

Where: Downtown Cambridge

What: Second Saturday in downtown Cambridge will be a festive one, as businesses come together to celebrate the holiday season. Simmons Center Market will be offering carriage rides starting at 5pm. Santa will also be hanging at the Market from 1-4pm before heading to Sunnyside Shop from 5-8pm for photos. Galleries and shops will be open later than usual to allow shoppers plenty of time for holiday shopping.

Weekend Wonderland in Bethany Beach

When: Saturday, December 12, 10am-6pm

Where: Bethany Beach

What: The holiday celebration continues for the second weekend in Bethany Beach, this time with Drop & Shop: Kids Day Out, featuring free movies for kids with certified childcare in the ballroom at Bethany Beach Ocean Suites. At 6pm, gather around for cocoa and caroling led by the Mariner Praise Band. Delaware Read Aloud will also be distributing books to children.

Christmas in St. Michaels

When: Friday, December 11-Sunday, December 13

Where: St. Michaels

What: For nearly 30 years, historic St. Michaels has celebrated the holiday season with three days of holiday fun during the second weekend of December. The event includes the Tour of Homes, Holiday Gala, Breakfast with Santa, and the largest Holiday Parade on the Eastern Shore.

Holly Festival

When: Saturday, December 12; 9am-3pm

Where: Downtown Milton

What: The annual Holly Festival of Milton includes a Christmas craft show at the Milton Fire Hall, along with the Milton Holiday House tour, which begins at 2:30pm and ends at 6pm.

Diakonia Breakfast with Santa

When: December 12, 8am-11am

Where: Lighthouse Sound, Bishopville

What: Diakonia and Lighthouse Sound invite you to Breakfast with Santa on Saturday, December 12. The menu will include scrambled eggs, pancakes, bacon, sausage biscuits and gravy, donuts, orange juice and coffee, along with holiday music and giveaways. Tickets are $10 for adults, $5 children ages 6-12. Cash or check only.

Holiday Block Party – 33rd-35th Streets in Ocean City

When: Saturday, December 12

Where: 33rd-35th Streets & Coastal Highway, OCMD

What: Ish Boutique, Planet Maze, Barn 34, K-Coast, La Quinta Inn, Guido’s Burritos, Senor Cigars, O.C. Wasabi, Tony Lukes, Ocean Atlantic, and Real Raw Organics are celebrating the holidays with a two-block holiday walk filled with specials on shopping, dining, and even accommodations. Entertainment and treats will be available as well.