The holidays in DC are magical—a blend of historic charm, festive energy, and endless date-worthy activities. From coffee shop meetups to ice-skating escapades, here’s a list of date ideas to inspire some serious holiday cheer (and maybe even a second date).
To make this guide extra special, we asked some members of our Compass Coffee team to share their go-to holiday date ideas. From free and fun to big-budget splurges, these are the places and activities our crew swears by to impress that special someone. No matter your budget or stage of the relationship, we’ve got you covered — straight from the coffee enthusiasts who know DC best.
Michael’s Date Idea: Cactus Cantina and Zoo Lights
Don’t Judge a Book by Its Cover, But Definitely Judge your Date by Their Coffee Order
The perfect holiday date in DC starts with Compass Coffee in Adams Morgan. You can tell so much about your date by their coffee order. Now, if you’re the CEO of Compass Coffee (cough, cough, hi), you might have an unfair advantage. Yes, I’ve looked up my date’s order history before. Don’t judge me. I’ll tell you about it, but only because it ended well.
Cue my first date with Sofia, now my wife. We went to ZooLights at the National Zoo, an event with twinkling lights, hot cocoa, and more Christmas cheer than you could ever ask for. Sofia didn’t know I owned Compass (not in my Bumble profile), and I had this “no talking about work” rule for dates. DC people love asking, “What do you do?” It’s boring, and I wanted to avoid it.
But 45 minutes in, I cracked.
Me: “What’s your favorite coffee?”
Sofia: “Oh, I love Compass!”
Me: Heart swelling. “What’s your go to?”
Sofia: “The matcha latte with oat milk.”
Record scratch. Matcha. Isn’t. Coffee.
Did I keep my cool? No. I told her I owned Compass Coffee and I’d looked up her order. “But hey,” I said, “I still agreed to this date, even though you’re technically not a coffee drinker.”
Good news: That was the last time I had to look up a date's order in our system. She’s now my wife. And yes, she’s converted to French presses and espresso capsules, but still enjoys the occasional matcha.
Cactus Cantina
An iconic DC Tex-Mex spot that holds a special place in my heart. I used to go there every Sunday after Hebrew school as a bribe. Bonus: it’s conveniently located right by the Zoo.
I get the same thing every time… skinny marg with salt. Boom. But my date (aka now wife) Sofia? No salt. Which makes NO sense.
As a kid, I was completely mesmerized by the flour tortilla machine at this iconic DC Tex-Mex spot. It sits right in the middle of the restaurant, churning out fresh, warm tortillas like magic—I couldn’t take my eyes off it. Honestly, this might be where my obsession with process machinery began. This place has been a staple in my life since the first Bush presidency (yes, that long). It’s massive—an unmistakable DC institution that every local knows. From prom dinners to birthday parties, the tortilla machine has been a witness to many of my life’s big moments. And let’s talk about the food—while I’ve tried other things, the fajitas are simply unbeatable. The combo chicken and beef is my go-to because, let’s be real, variety is key. They’re served with corn tortillas (and, obviously, I’m pro-paleo, but that’s a story for another time). Every once in a while, a mariachi band will show up, adding to the festive vibe. Speaking of festive, there’s a massive cactus decked out with Christmas lights that they leave up year-round. It’s cheesy, but I secretly love it. This place has been part of my life for decades, and every visit still feels special.
Sydney’s Date Idea: Cocktails & Curtain Calls
For a holiday date that mixes sophistication with a little edge, drinks and a show is the way to go. Start with a stop at Off the Record, a speakeasy tucked under the Hay-Adams Hotel near the White House. It’s cozy, a little mysterious, and has the perfect vibe for pre-show cocktails. If your night involves the Kennedy Center (my personal favorite), Georgetown is packed with great spots to grab drinks beforehand — including our theater-inspired Compass Coffee! (The best option if you need a quick boost to stay awake for the show.)
As for the show? You can’t go wrong with DC’s iconic theaters. The Kennedy Center is my go-to, where I’ve seen incredible performances like Moulin Rouge, Hamilton, and Mamma Mia. If you’re feeling adventurous, the Warner Theatre is a solid contender — shoutout to Batman in Concert, which might just be my all-time favorite show. (A live orchestra playing the score of the Dark Knight? Absolute chills.)
One thing you won’t catch me at? Traditional Christmas shows. Call me a Scrooge, but The Nutcracker and It’s a Wonderful Life just aren’t my thing. Give me a unique, jaw-dropping performance any day — it’s way more exciting, and honestly, more memorable. Pair that with great drinks, and you’ve got yourself a show-stopping holiday date.
Gabby’s Date Idea: The Botanical Garden’s Holiday Display
Okay, here’s the move for a holiday date that’s equal parts cute, fun, and totally IG-worthy. Oh, and did I mention its WARM year round? First stop: coffee (duh) at Compass Coffee’s Navy Yard North cafe for good vibes and caffeine. From there, it’s just a quick stroll over to the US Botanic Garden, where the holiday magic is straight-up next level.
Their “Season’s Greenings” exhibit is SO cool — it’s all your favorite DC landmarks, like the Washington Monument and the Capitol, completely recreated out of plants. Yes, plants. We’re talking bark, leaves, and other random natural stuff turned into insanely detailed mini versions of iconic buildings. It’s giving art meets holiday Pinterest board, and I’m obsessed.
Oh, and here’s the best part: this year they’ve added an Inciardi Mini Print Vending Machine. For one dollar (four quarters, people), you can get a collectible print that’s both adorable and artsy. It’s like Pokémon cards, but cooler—trade with other visitors if you’re feeling extra. Trust me, this is the kind of date that’s perfect for your feed and your vibe.
Things went well? Congrats! You’re onto date #2! Try these next dates on for size.
Sydney’s Second Date Idea - Holiday Market & Iconic Ice Skating
My husband is from California and I’m from Texas, so you can imagine that we get an irrational level of excited anytime anything related to snow or ice is involved. And when it comes to iconic dates, you can’t do better than ice skating next to a literal Smithsonian, or shopping in front of the National Portrait Gallery. So it’s no surprise that these two dates are our top choices.
But why is it for a second date? The first date was all dim lighting and fancy theaters, but now, you’re about to get vulnerable. You’re likely about to slip and fall on your butt in broad daylight. But hang in there, I’ll explain why it’ll actually be cute.
Downtown DC Holiday Market
Obviously, the first stop is coffee. And lucky for you, Compass Coffee in Chinatown happens to be right next to our first stop. Cutler always gets a hot vanilla latte with an extra shot, and I always gravitate to cold brew (yes - even in the winter.) Once your coffee is secured, head to the Downtown DC Holiday Market (literally 20 steps away.) It’s packed with local vendors, delicious food, and gift ideas galore. My personal favorite is Cherry Blossom Creative — they make watercolor maps of DC neighborhoods that are perfect for holiday gifts. Plus, the stuffed churros are to die for… just don’t count how many you eat.
Ice-Skating at the Sculpture Garden
Nothing screams "holiday date" like ice skating. The National Gallery of Art’s Sculpture Garden Ice Rink is hands-down one of the best spots for a festive DC adventure.
Here’s the thing about ice skating: you don’t have to be good at it — you just have to be better than your date. (; That’s why I only ice skate for dates. It’s the ultimate excuse to hold hands, maybe do the classic “oh no, don’t fall!” touches, and just be silly. Texans don’t ice skate, so when you’re as terrible as I am, you can’t take it too seriously. And hey, if you’re really bad, the rink offers lessons — but let’s keep that little secret between you and the instructor.
Here’s the genius of this date idea: the more dates you go on here, the better you get. Even if the relationship doesn’t pan out, you’re building skills for the next one. Each date will be progressively more impressed with your skating prowess. Talk about playing the long game.
Pro Tip: This rink transforms into Jazz in the Park during the spring, which is another killer date idea. Stay tuned for our spring date guide — it’s coming in a few months!
Michael’s Second Date Idea: Navy Band Concert + Old Ebbitt
If Zoo Lights and skinny margaritas (with salt, obviously) were a hit for your first date, this second date idea is guaranteed to keep the holiday magic going. Start with the United States Navy Band’s holiday concert. While I’ll always argue the Marine Corps has the superior band and Sunset Parade, they sadly don’t have a holiday concert. Luckily, the Navy Band more than delivers with festive tunes in one of DC’s most iconic venues—it’s the perfect mix of history, tradition, and holiday cheer.
Afterward, take a moonlit stroll past the White House Christmas Tree. It’s twinkly, romantic, and gives you a chance to continue that sparkling conversation from Zoo Lights—bonus points if you throw in some lighthearted ornament debates. Then, make your way to Old Ebbitt Grill for dinner. This place is the definition of a DC institution, and during the holidays, it’s all decked out like a scene from a Hallmark movie (but with better food). They’re open until 2 AM, so whether you’re craving a burger, oysters, or just a cozy booth for lingering over drinks, they’ve got you covered. Wrap things up with a late-night nightcap, and maybe even a little mistletoe moment if the vibes are right. This date is festive, fun, and has just the right amount of DC flair to keep the sparks flying.
Sydney's Favorite Date Idea (You'll See Why)
If you know anything about me, you'll know that I love animals. Specifically, cats. So when I found out that Old Town had a CAT WINE BAR, I almost LOST IT. (That's exactly why this is my favorite date idea over all.)
Here's how it works: you make a reservation on Mount Purrnon's website. I know, I know. It's the cutest name ever. When you walk inside you enter on the first level, where a wine bar awaits next to a warm and cozy fireplace. They obviously have wine, but they also have a full menu of coffee, beer, cider, espresso, and snacks! There's plenty of space to sit and relax downstairs, or you can take your drinks and head upstairs where the magic happens...
When you walk upstairs, you'll enter a room that will bring even the most macho man to his knees. Dozens of rescue cats and kittens run around playing with toys, lounging on couches, and sitting on laps. I could have died from excitement. Oh, and ALL of these little fur babies are available for adoption. Each reservation gives you an hour to play and snuggle with all the cats to your hearts desire. The staff are all sweet and knowledgable, ready to answer any questions you have. They also host frequent fun events like tarot card reading, book swaps, cat yoga, and wine tasting. In my book, this is the perfect before/after dinner spot to get that dopamine pumping EXTRA high.
If you can't make it to the cafe but want to support this awesome animal rescue business, you can donate on their website or purchase items from their Amazon wishlist.
Bonus… Jewish Things!
If you’re looking for a date idea with a little Jewish flair (and a lot of personality), start with Ivy and Coney. Located right next to the very first Compass Coffee in Shaw, Ivy and Coney is the dive bar of your dreams—or nightmares, depending on your tolerance for Malört. Back in the spring and summer of 2014, when we were meticulously building our first, quaint Compass Coffee, Ivy and Coney was under construction next door with a completely opposite vibe: a no-frills Chicago-style bar with beer, hot dogs, and zero patience for nonsense. Want a cocktail? They’ll probably tell you to get the hell out and remind you this isn’t the Ritz.
Despite our polar opposite approaches, Ivy and Coney has been a longtime neighbor and friend. They lean into their identity hard, especially during the holidays, when the bar transforms into a Hanukkah wonderland. We’re talking dreidel decorations, menorah displays, and festive lights. And then there’s Malört, the Chicago liquor infamous for its face-contorting taste. If you’ve never had it, you owe it to yourself to order a shot and experience what’s known as “Malört face.” (Fair warning: it’s horrible, but hilariously so. Make your date try it and see who survives.)
If you’re still standing after the Malört and hot dogs, take it to The Matzah Ball, a legendary Jewish dating event. Start the night at Decades for dancing and socializing, then swing by Ivy and Coney for late-night vibes, a shot of Malört, and a mint — you might need it. (;
Take the Chance
There you have it—a foolproof plan for a fun, festive, and slightly ridiculous DC holiday date. Whether you’re sipping coffee (or silently judging their matcha), laughing on the ice, or marveling at plant-based monuments, the key is to just go for it. Ask that person out. Put yourself out there. Worst-case scenario? You become a better ice skater.
Happy holidays, DC. Let’s make some magic.
