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Christmas, Holiday

Single During the Holidays

December 9, 2025 by Tyler Ingle

Who says the holidays are just for couples? Being single during the holiday season opens up endless opportunities to make the celebrations completely your own. From spontaneous solo adventures to new traditions built around what you love most, flying solo isn’t as bad as it’s made out to be. Coming from someone who is spending another holiday season single, I’m letting you in on some of the best ways to create your own kind of joy.

Midnight Madness

Taking place on the first two Thursdays of December (4 PM to midnightt) and the third Thursday of December (4 to 11 PM), this Annapolis staple is the perfect way to charge up that holiday spirit! Whether you’re looking to spend time outside in the wintery ambiance or have a mission to grab the perfect gift for a family member, Midnight Madness creates a fantastically jolly night for all. My biggest tip here, for those struggling with being solo, is to focus on the sights and sounds, the lights, trees, window displays, and pay less attention to the people.

Performances

Theatre and musical venues always see an uptick in events during the holidays, giving you plenty of options to embrace the performing arts. Annapolis hosts several performances by the Annapolis Symphony Orchestra at various locations. Live Arts Maryland will be performing Handel’s Messiah, while the Ballet Theatre of Maryland will see the return of The Nutcracker. The Classic Theatre of Maryland will present A Christmas Carol and a White Christmas, with Rams Head on Stage hosting a variety of musical guests. If you’re willing to go further, there are plenty of theatres in D.C. and Baltimore that will be putting on shows for the holiday, too. Let’s not forget, buying one ticket is always cheaper than buying for two!

Light Displays

With several displays to choose from, Lights on the Bay has been a mainstay in the Anne Arundel County community for 31 years. This drive-through light display also offers two nights where you can walk-through with your furry friends. The Merriweather Symphony of Lights, a bit further away, runs until January 3rd. This light display is a drive-through event, with select nights being open for a walk-through! 

Movies and Sports Games

While the least festive of the bunch, sports games are always a great opportunity to get out! Whether it’s a Navy hockey or basketball game, a Washington Capitals game or Wizards game, or supporting a minor league team, sports games offer a community-centric feeling with the fan base while being easily able to keep to yourself while there if you prefer. Additionally, many theaters will show special holiday movies, such as Elf, The Polar Express, and more, for a discounted rate. The winter also sees several new movies released, and there’s no better way to get the full experience than heading to the theater (AMC at Annapolis Mall is always a great option!). 

Simple Yet Overlooked Tips

Sunshine! Yes, it’s cold outside, but even 15 minutes in the sun can make a huge difference in your overall mood. It’s not great being sick during the holidays. Hydration tends to go by the wayside. When we’re colder we don’t have that same thirst for water, but make sure you’re getting down the fluids! Looking to stay warm? Tea, coffee, and bone broths are all great options, too!

Don’t forget to prioritize family and friends! Just because you don’t have a significant other doesn’t mean the holidays are a dud. Odds are, you still have people in your life who care about you and are thrilled to be in your presence! Volunteering can also foster a great sense of meaning and community!

Finally, be willing to feel your feelings. Suppressing and ignoring them may seem good at the start, but they ultimately will be harder to deal with down the road. Make sure to treat others with kindness throughout this time – a simple smile can go a long way!

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Related posts:

Call Your Mother: Bagels Every Mother Could Love Save The Date List SQRRL! several people on lit stage playing instruments and singing in Christmas costumes and a squirrelAnnapolis Moms Presents: SQRRL! Family Fun on December 23 at Rams Head Springtime Fun in Historic Annapolis: Mr. Paca’s Garden Storytime & More!
Category: Christmas, HolidayTag: adults, Holiday, single See all posts by Tyler Ingle

About Tyler Ingle

Previous Post:Celebrate the Season in Annapolis with Watermark’s Holiday Experiences
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🍂 PUMPKIN SPICE AND EVERYTHING NICE! ☕

Fall calls for cozy sweaters, crisp air, and a coffee that tastes like the season. From pumpkin spice lattes and maple cream cold brews to apple chai and snickerdoodle drinks, local
Annapolis-area cafés are serving up plenty of fall flavors worth trying.

We rounded up our favorite stops for seasonal sips, sweet treats, and cozy café vibes, including beanrushcafe The Big Bean Brown Mustache Coffee™ Ceremony Coffee Roasters Kozy Beans Coffee - Crofton, MD Rise Up Coffee Roasters and Wyrd Bookstore

Save this guide for your next coffee run, and tag your fall coffee buddy!

👉 Read the full guide here: annapolismomsmedia.com/our-fall-flavor-coffee-tour-
of-annapolis/

#annapolismoms #LocalFoodFinds #fallflavors #CoffeeLovers
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A little romance, a

A little romance, a little laughter, and a whole lot of Broadway magic are headed to Annapolis this November!

Live Arts Maryland is bringing the beloved music of Rodgers & Hammerstein's OKLAHOMA! to Maryland Hall for TWO special evenings celebrating one of the most iconic musicals of all time.

From Oh, What a Beautiful Mornin' to People Will Say We're in Love and The Surrey with the Fringe on Top, these are the melodies that have captured hearts for generations. And there's something especially wonderful about hearing them brought to life in concert!

Whether it's a longtime Broadway favorite or a first introduction to the music of Oklahoma!, this is a wonderful opportunity to enjoy timeless songs, beautiful storytelling, and a little Broadway nostalgia right here in Annapolis. ❤️

As a proud Annapolis Moms Community Supporter, Live Arts Maryland loves being part of a community that celebrates the arts and creates opportunities for local families to experience the joy of live music and theater together!

🎭 Rodgers & Hammerstein's OKLAHOMA!
📅 November 13 & 14, 2026 | 7:30 PM
📍 Maryland Hall | Annapolis, MD

Make it a date night, plan a fun evening with friends, or gather the musical theater lovers in the family. It's the perfect excuse for a night out in Annapolis! ✨

🎟️ Reserve your seats now!

#LiveArtsMaryland #AnnapolisMoms #OklahomaMusical #RodgersAndHammerstein #AnnapolisEvents
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