facebook pixel

Our May Guide to NYC

It’s almost summer in the city, but for now, we are rounding out spring in New York City. Beyond exploring the beautiful Central Park, seeing a Broadway show you have had on your list for awhile and shopping on Fifth Avenue, there is so much to see and do here. The big apple is always the best time and full of family-friendly activities such as going to Yankee Stadium, dining in Little Italy and seeing live musical performances. Get your comfortable walking shoes on becauseI have found the best things and special events to check out in the city at this time of year. Come for the delicious food and stay for the iconic attractions, this is everything to do in NYC for a short amount of time even, this May.

may nyc things to do

North River Sailing

We love to get on the water and see all the amazing views of the city. North River Sailing is a company that will give you a tour of Manhattan–from the water! Begin at Brooklyn Bridge and they even offer sunset cruises! What’s really unique about them is they are BYOB and super chill, so they will even let you help sail if you’d like! I highly recommend for a day activity or to end the day and watch the sun set. They have 4 sails a day and tickets are available on their site.

Lincoln Center Summer Festival

Lincoln Center does “Summer for the City”, which is a festival that’s just like a legit music festival you see everyone attending all summer. There are dance performances, live music and so much more! They will be releasing all of the information soon, so make sure to sign up on their site to get notified when it all gets released!

Watermark Picnics

The Watermark Bar on Pier 15 is one of my fav spots! They have some great food and drinks and the views overlooking the water are always stunning. This month, there is a ton going on and they officially open on Cinco De Mayo! The Cooler Packages will be available and include your favorite canned and bottled beverages ready on ice. They are transforming into a tropical oasis to kick off to the summer and you won’t want to miss it!

may nyc things to do

Grab Brunch

One of our favorite things to do is get a great brunch in the city! There are endless places to enjoy, but of course, we have our favorites. We recently shared our favorite spots for Mother’s Day brunch and I’d have to say, it’s a great list! Here’s another list of places we enjoy, too! Stay tuned for updates as the month goes along.

Moxy Activations

The Moxy in Times Square, Williamsburg and Chelsea all have such fun Mother’s Day activations this month! Up until the 12th, the Moxy Times Square will partner with Dopl to create the most amazing miniatures that make for perfect gifts. Sign up for a cupcake decorating class with Polly Cooks at the Moxy Chelsea on the 11th from 2-3:30. It’s more fun if you bring your mom, sister or friends! Finally, the Moxy Williamsburg has a super cute puppy yoga class on the 25th. Relax and play with the sweetest pups to wrap up the spring season!

Go to Rooftop Bars

It’s officially rooftop season and us New Yorkers are thrilled! To be able to get fresh air while enjoying timeout with friends is something we take for granted when the cooler months come. I have a whole list of our favorite cocktails in the city here. You’ll have to let me know if I missed any!

Spring Makers Market

We’re big market people! Finding markets to walk around and find fresh foods and enjoy the spring time weather at is something that is underhyped. We should be talking about it more! Bryant Park will be opening this new spring market for four weekends this month. There are tons of vendors with beautiful hand-made items to shop from. This is the perfect place to get gifts as well. It officially opens May 3rd and runs through the 27th.

Cinco de Mayo

Cinco de Mayo is the perfect holiday to enjoy amazing food! A few of our favorite taco spots are Los Tacos No. 1, Tacqueria St. Marks Pl, La Esquina, Empellón and La Superior. We can’t forget about margaritas! A few great spots are Fool’s Gold, The Black Ant, Fonda, Cosme and Cantina Rooftop! If you want to have a party and make tacos and margs yourself, that’s even better!

may nyc things to do

Cedar + Branch Mother’s Day Wellness Experience

On the 12th from 10AM-12PM, Cedar + Branch is having a wellness experience for moms. Tickets are $150 and you will get to experience a yoga session, sound bath and meditation and soundscape experience. This is the most relaxing event of the month and I strongly encourage everyone to take part in it!

Play Street Museum

There’s a new play area in town on the Upper West Side! This is an educational and incredibly fun spot to bring your kids to and it caters to kids from the toddler stage up to age 8, so there’s plenty of activities and fun to be had for your kids! The interactive space has hands-on activities and is a great place to have a birthday party, event or even suggest to schools as a field trip option.

Loews Regency Mother’s Day

You all know how much my girls and I love staying at the Loews Regency! I was so excited to hear that they actually have Mother’s Day programming this year to take part in from May 10th-12th. There are things like a spring shopping pop up in their lobby, bouquets you can buy for the special woman in your life and a special brunch with delicious seasonal specials to enjoy at their restaurant The Regency Bar & Grill, but grab a reservation to be safe!

Memorial Day

Memorial Day is to celebrate and remember all of those who have fought for our country. It’s a weekend of rest and celebrations and that’s exactly what we should be doing! There are tons of restaurants open and ready for reservations, but if you can get out to the Hamptons or Jersey Shore to spend some time at the beach and get some sun, I highly recommend doing so!

Five Boro Bike Tour

Can you believe the Five Boro Bike Tour is already sold out for registration?! I’m so proud of all of the riders and excited to watch from the sidelines! On Sunday, May 5th, you can watch the bikers ride throughout the city and cheer them on! They have been training for so long and there will be jazz music, cheerleaders and more entertainment throughout the tour. Plan to not take any cars that day!

International Food Festival

Food festivals are opportunities that provide great ways to learn about other cultures and try new foods. Located on 9th Avenue, near Times Square, on May 18th-19, you will be able to enjoy some of the best foods in the entire world! They will be running from 10AM-6PM, so you have all day to check it out, but it will be crowded so bring water and cash to be safe!

Mother’s Day

Mother’s Day is May 12th this year and there truly are endless options of ways to celebrate. Grab brunch, have a picnic in the park or even just spend time together at home. Quality time is overlooked and sometimes we don’t realize we are missing it until we get it. Personally, I love seeing Broadway Shows and grabbing dinner at one of my favorite restaurants. I’ll be happy as a clam if I can do that! Moreover, a lot of spots have specials like Pokeworks, where you can get 20% off any regular or large poke bowl with the code: MOMSDAY24. This can be used both in store and online!

Japan Fes

If you haven’t been to Japan Fes, you are missing out! It’s the largest Japanese food festival in the city with over 1500 vendors. We always look forward to getting ramen here, but the vendors are all over the place including Chelsea, Park Slope, the UWS and Greenwich Village. Check out their site to see which dates they are at which location.

may nyc things to do

Sip & Stitch

This is on my list of things I will be planning for a girls night out with my friends! This is a workshop you can book with groups to make your very own handbag. How fun is that? I think it’s perfect for a birthday party or celebrating an engagement because you can make your very own creation. They can host up to 25 people for private celebrations and you can’t beat getting a purse at the end of the night!


Calling all foodies, you are going to want to check this one out! Smorgasburg is the largest open air food market here! This is one of the more popular attractions food-wise in the city. They have a ton of different vendors with food ranging from BBQ to cookies to ice cream to sandwiches and all the way back. You’ll want to keep up with their schedule, though, to make sure you know which locations are open on which days and times and that’s all on their site here. They also have their full list of vendors to scope out on there. With several different locations, you can find the closest to you and head over! This is also one of the more popular events for families and is super kid friendly!

Paul McCartney Exhibition

The Brooklyn Museum has one of the most iconic attractions of the season! I think we’re all Paul McCartney fans here and this exhibit is photographs from 1963-1964. It’s called Eyes of the Storm and showcase Paul’s history. It’s a mix of video and photographs and something you will not want to miss!

Hester Street Fair

We love going to street fairs because there’s so many new things to be discovered. From accessories to jewelry and home finds, this is another place to get gifts from! I bring the girls and we make a whole girls day out with it. A little shopping is always a yes from us! Shop local businesses in the Seaport every weekend this month!

Hope For Depression Teen Race

On May 19th, the Hope for Depression Research Foundation will be holding its second annual teen race starting at 10AM on Pier 76. This 5k race will have all proceeds go towards research for the root cause of depression in the brain and aid in the search for treatment. You can run or walk and tickets are $17.50 for students and $27.50 for adults. Sign up here!

Whitney Biennial

One thing about NYC is that we have some of the best art here! The Whitney Biennial is something we always go to because it’s a great way to explore pieces and learn about art. It’s actually open until August 11th, so if you’re in town any time this summer, you can catch it!

may nyc things to do

Asian Comedy Festival

Jason and I love comedy shows and this is one of the best around! This festival is the largest to support the Asian  and Pacific Islander community and the talent there is unmatched. Tickets are on sale for performances May 7th, 14th and 15th! Make a whole date night out of it and laugh the night away.

Alice in Wonderland Floral Exhibit

The New York Botanical Garden does it again with a super cool exhibit! This is open May 18th-October 27th, but it’s one you will definitely want to check out in the spring and summertime. All of the sights, smells and settings are based on Alice in Wonderland and it’s a whole world of imagination, which is great for the kids! They have large chess pieces and afternoon tea, so you will want to spend the better part of your day there.


For more NYC happenings, visit here!

may quote

Pin it!

may nyc things to do
may nyc things to do

Join The Conversation - Comment Below

Leave a Comment

Your email address will not be published. Required fields are marked *