Take a ride with Santa on a historic streetcar during the Holly Trolleyfest at the National Capital Trolley Museum.- Stroll through holiday themed artwork at December in the Galleries in North Bethesda.
- Grab tickets to the American premier of a holiday family drama, Rules for Living at Round House Theatre
- Celebrate 60 years of Snoopy and Charlie Brown at A Charlie Brown Christmas Party in Laytonsville.

- Take in the holiday lights under a 50-foot Christmas tree at Winter City Lights.
- Taste award-winning wines at Metzger Winery’s Christmas Pop-up Tasting Room in Poolesville.
- It’s Winter Fest all weekend at Song Dog Farm Distillery, grab your pups and get ready for a night of cocktails, Santa, food trucks, and holiday games!
- Dress your worst and spread holiday cheer at Hip Flask’s Ugly Sweater Party.
- Stop by the Whispering Spirit Speakeasy for Sounds of the Season Jazz Night.
- Listen to Cassie & Maggie – A Celtic Christmas at BlackRock Center for the Arts.
- Shop for last minute presents this weekend at Merry Market in Rockville.
- Bowl With Santa to strike up some holly-jolly magic at Lucky Strike Rockville.
- Sing nostalgic holiday songs and wear your most outrageous knits to Waredaca Brewing Company for their Holiday Song Sing Along & Ugly Sweater Party.
- Purchase gifts, take pictures with Santa, and listen to a DJ spinning holiday cheer at the Holly Jolly Shopping event at The Shops at Wisconsin Place.
- Bring the family to The Winter Jubilee at Rockville’s Civic Center Park for a night of games, arts and crafts, and costumed characters.
- Become enchanted by the timeless tale The Nutcracker at Montgomery College.

Extended Weekend Getaways