11 Ways to Enjoy Union Square During the Holidays

One of the many reasons we call Union Square home is that you never have the same travel adventure twice — and that’s especially true during the holidays. Take this travel guide with you for your most festive stay in lower Manhattan and ring in the holidays with an extra infusion of cheer.

1. Union Square Holiday Market

First things first: You can’t talk about the holidays on 14th Street without bringing up this iconic holiday market. More than 150 booths serve up treats of every sort; whether you have a sweet tooth, need more holiday decor, or get the gift shopping done, this place has your seasonal wishes fulfilled. And the ambiance? This stop is 10/10.

2. The Strand Drag Show

Books and Queens will make your evening slay ride one to remember thanks to Christmas at the Strand hosted by Kendall Knight. Put a travel notice in your calendar for December 15th and make your way to New York’s iconic bookstore for the cheerful caroling, a raffle, cocktails and mocktails. If you can’t make the festivities, the Strand also has a Holiday Shop to get the ever-so-royal holiday fix.

3. Gotham’s Day of Holiday Dining & Music

Touted as an “all-day holiday dining and music extravaganza” on December 17, Gotham brings a Jazz Lunch that serves up three courses accompanied by the famous Tri-state Dal Segno Trio. But wait, there’s more. For the evening’s festivities, the Ted Nash Big Band (feat. Kristen Lee Sergeant) launches a holiday-themed album with a specialty menu. However, if you’re already booked that day, be sure to visit Gotham anyway for its chef’s-kiss menu — plus it’s a feast for the eyes, too, with a full gallery of books and art.

4. Visit ghosts of holidays past on the Greenwich Ghost Tour

If you’re willing to go off the beaten path, may we recommend the Greenwich Ghost Tour. Get your steps in as you step back in time to explore the tales of the Hanging Tree, get acquainted with 22 ghosts at the most haunted house in Manhattan, vote for a former mayor of Gay Street, and sightsee many more connecting stops. It’s Scrooge-approved.

5. Elevate your hot cocoa at Blue Stripes Cacao Shop

The bald father of iconic chocolate haven Max Brenner, Oded Brenner himself, launched Blue Stripes in 2022 and is reinventing chocolate yet again. This first-class shop uses the whole cacao bean to craft truly delicious chocolatey masterpieces. And with all the cacao superfruit properties, you’re actually doing something for your health by stopping by and ordering a hot chocolate. Or Nutella roll. Or a pain au chocolat. Or a cacao latte. Or… you get the gist.

6. Lillie’s Victorian Restaurant brings the holiday vibes

It’s easy to get into the holiday spirit when the vibe is right, so make your way to Lillie’s Victorian Restaurant on 17th Street. They deck every inch of their halls with cheer as a perfect backdrop for seasonal cocktails, merry mocktails, and festive feasts. Santa’s also been known to make a pitstop here from time to time.

7. Amsterdam Billiard Club

Amsterdam may be a bit far this time of year, but a getaway Amsterdam Billiards club doesn’t require airfare. If you need a different kind of get-together this season, aside from a rousing game of pool, this hub also has ping pong, darts, foosball, and so much more on the menu. You might even get lucky and see some twinkling stars (AKA celebs) run the table.

8. Try a frosty treat at Amorino

Exchange your hot cider for something a touch colder. The gelato geniuses at Amorino on University Place. announced their newest wintery treat: dado gelato. Inspired by ice truffles, the dado features two gelato flavors and is dusted with cocoa. Inside tip: pair the dado gelato with any of these fine gelatos.

9. Pick up donuts, latkes, and babka at Breads

The Breads Bakery Union Square flagship location can whisk you away from the hustle of the holidays and land you in a wonderful world of baked goods. Aside from pastries, cookies, and cakes, you can pick up the city’s arguably most popular challah bread. And until December 17th, you can schedule pick-up or an order of family-sized Hanukkah delights such as sufganiyot, rugelach, and more.

10. Ring in the holidays with a comedy show

If long winter nights got you down, The Stand has an almost-daily rotation of laugh-out-loud line-up gold. As we all know, comedy and cannabis are longtime friends, so be sure to reserve your seat early for the best viewings.

11. Stop by Forbidden Planet for gift shopping

Find the classics and the newest releases of all things comic, graphic novels, manga, cards, collectibles and more and this one-stop-shop utopia. Forbidden Planet is located in the heart of Union Square — and sci-fi fans everywhere. We won’t tell if all the gift shopping you actually get done is for yourself.

Start — or wrap up — your Union Square travel with a cannabis stop

As you wind up or wind down your high-venture through Union Square, stop into The Travel Agency for your favorite treats. Skip the line, order ahead, and pop in before you get your shopping done. With 300+ products, there’s something for every mood on our menu.

We welcome you to end your trip to Union Square’s most festive season with us. After all, ‘tis the season for gifting, so check out our high-curated holiday gift guide before your stop in for some great ideas for what you can bring home for the cannabis consumers in your life.