Going to New York? Here are tips for pregame fun, eating near Madison Square Garden, and more

I went to New York City for the first time in December 2009 to see John Calipari’s Kentucky Wildcats play UConn in the SEC/Big East Invitational. I drove there from Lexington through a snowstorm in the Appalachian Mountains, which made the one-way drive somewhere north of 20 hours without stops. We piled three people into a two-star hotel room. I ate a punch at the game. John Wall scored 25 points in a Kentucky win. It was awesome. I fell in love with New York City on that trip.

Since then, I’ve been back close to 30 times in 15 years. I was even all set to get married in downtown Manhattan in 2020. But as you can imagine, we had to cancel those plans given the circumstances. I made up for it with a bachelor party in New York a couple of years later. I was up there just a month ago, too. I’d love to be there again this weekend to support Mark Pope’s Wildcats in the CBS Sports Classic, but I couldn’t pull this one off.

Anyway, enough about me and my obsession with the best place on Earth. YOU are going to New York, and you’re going to have a great time. Kentucky will beat the Buckeyes. You’ll see the Christmas lights. You’ll eat some good food. Ugh, I am so jealous, but not too jealous to leave you some recommendations if you need them. Let’s start with the home base for Big Blue Nation:

Jack Demsey’s

If you’re in New York for a Kentucky game, any list of recommendations must start with Jack Demsey’s. It’s the official UK bar in the city, home to the UK Alumni Club and game-watch parties for every Kentucky game. It’s also conveniently located near Madison Square Garden, just a short and straight walk east on 33rd Street. Head there before and after the game to be around Big Blue Nation. You’ll see the Kentucky flags flying out front. Tell everyone I said hello, too. Man, if those walls could talk.

I’ll share Jack Demsey’s schedule for the weekend at the bottom of this post.

Where To Stay In New York

You should already have a place to stay. If you don’t already have hotel accommodations, good luck. I usually stay in Chelsea because it’s far enough away from the mayhem of Midtown but close enough to pop into the mayhem on a walk.

Where To Eat Near Madison Square Garden Before/After The Game

There is amazing food all over New York; however, the area surrounding Madison Square Garden is not exactly a hot spot for cuisine. Still, there is good food to be found beyond the neighboring McDonald’s and Panda Express.

• NY Pizza Suprema – We’ll start with the obvious: NY-style pizza. You’ll find pizza by the slice in every direction you look around Madison Square Garden. One in particular is NY Pizza Suprema on the corner of 8th and 31st, with a longstanding reputation as one of the best slices in the city.
• Los Tacos No. 1 – The best tacos in New York are at Los Tacos No. 1, with a location next door to Madison Square Garden. There are six other Los Tacos No. 1s around New York, which is confusing, but they all serve the best tacos you’ll find.
• Tick Tock Diner – If you’re into touristy things, consider another neighbor to Madison Square Garden: Tick Tock Diner. It’s a classic American diner, one with iconic status in Manhattan since its opening in the 1940s.
• Keens Steakhouse – For a high-end pre or postgame meal, Keens Steakhouse is around the corner. However, you should’ve made that reservation weeks ago. Maybe you can luck into a walk-up table, but don’t count on it.
• Jack Demsey’s – Order a Shepherd’s Pie to soak up all of that cold beer during the pregame fun. Or surprise your group with an appetizer medley for the table.
• Legends – If Jack Demsey’s is too crowded, walk a little further to Legends. The bacon-wrapped jalapenos and the four-cheese mac n’ cheese are KSR-approved. Don’t judge the place for being the LSU bar. It’s the same ownership as Demsey’s, so it’s in the family.
• Koreatown – The Garden is a block from Koreatown, so you have several authentic Korean options nearby if you’re interested in branching out to new cultures. The game will be finishing up around dinnertime, so consider an immediate celebration with bibimbap and Korean BBQ. Turntable Chicken Jazz is the place for Korean fried chicken, also on W 33rd.
• Dim Sum Palace – After Kentucky’s last game in Madison Square Garden (a loss to UCLA in the 2022 CBS Sports Classic), the KSR crew tried to escape its sadness with late-night dim sum. Dr. Mike, who we trust on the subject, led us to Dim Sum Palace, directly across the street from Jack Demsey’s on W 33rd. You wouldn’t know it by our one photo, but we did eat food that night. It got the job done at 11 p.m.

Christmassy Things To Do When You’re Not Watching Kentucky vs. Ohio State, Rockefeller Tree Not Included

Unless you’re a Scrooge, you can’t go to New York in December without embracing the city’s Christmas spirit. So, here are some things to do before drowning yourself in the sea of people around the Rockefeller Center. Don’t go see that tree if you’re uneasy in large crowds.

• Shop, eat, and skate at Bryant Park – Not far from MSG is Bryant Park, which turns into a winter village this time of the year. There’s ice skating, tiny little shops in the holiday market, lots of good food, and holiday fun for the whole family. Beware: it will also be very crowded, as will most items on this list.
• Walk, skate, or ride in Central Park – More ice skating can be found in Central Park. With snow in the Saturday morning forecast, this weekend may be a good time for a scenic walk through the park. Maybe even hop in one of those carriage rides with Mariah Carey blasting from a portable speaker if you’re really feeling the holiday cheer.
• See the window displays at Macy’s – The Macy’s in Herald Square is slightly different than the one in Fayette Mall. If you’ve never been, it’s worth a peek at the Christmas window displays, the famous BELIEVE sign, and the sheer size of the department store. If you like the window displays, find more at Bloomingdale’s, Bergdorf Goodman, Saks Fifth Avenue, and any department store you pass. Just keep walking toward any bright lights. There are more.
• Toast to Christmas at McSorley’s – OK, McSorley’s is not a Christmas activity. It is the old Irish ale house that has been around since the 1850s. McSorley’s has some Christmas garland and lights strung up for the holidays, but otherwise, it’s just a great place to go back in time with a mug of light or dark. Cash only. Get the cheese plate.
• See the decorations at Rolf’s – Christmas-themed bars are like pizza shops these days, so I will direct you to a German restaurant, Rolf’s, near Gramercy Park, for one of the more uniquely decorated spots. Drinking a chocolate martini at Rolf’s is the closest I’ve ever been to the North Pole. Look at all of these ornaments:

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Jack Demsey’s Saturday Schedule

• 12 p.m. | Hoops There It Is
  Join the New York City UK Alumni Club as we prepare to cheer on the Wildcats during the CBS Classic! We’ll be Rockin’ Around the Rockefeller Tree with fellow Kentucky alumni, celebrating hoops, holiday cheer, and all things Big Blue. Don’t miss this festive gathering in the heart of NYC then walk to Madison Square Garden for the game!
• 2 p.m. | The Goose Who Saved Christmas: Jack Givens Book Signing
  Celebrate the holiday season with Kentucky basketball legend Jack “Goose” Givens! Join us for an exclusive book signing event on the second floor at Jack Demsey’s. Relive iconic Wildcats moments, and take home a signed copy of his new book, They Call Me Goose: My Life in Kentucky Basketball and Beyond.
• 3 p.m. | North Carolina vs. UCLA
• 5:30 p.m. | Kentucky vs. Ohio State
• Post-game | From Buckets to Jingles: Wildcats Postgame Bash
  Celebrate after the game with live music! Join Big Blue Nation as we go from a win to holiday cheer, mixing basketball vibes with NYC holiday magic. Don’t miss the ultimate post-game party!

Have fun, and bring home a win.