Our Full Guide to May in NYC

Posted by

On May 2, 2025

Summer is on its way to New York City! Of course we love to enjoy Central Park, see the best Broadway shows, shop on Fifth Avenue, seeing the Statue of Liberty and High Line. The big apple has some fantastic family-friendly options to explore and it’s one of the best places to go visit at the start of the summer. It’s perfect average temperatures before the summer months begin making it a great time to explore outdoor activities in the city. If it’s your first time here or you are a local looking for activities for a long weekend or just a good time, these are the top things we are looking forward to doing this time of year in the city!

Printemps, the iconic French department store, has opened its first American location at One Wall Street in the Financial District. Covering over 55,000 square feet across two floors, the store features interiors designed by Laura Gonzalez to resemble a Parisian apartment, blending Art Deco and modern elements. A highlight of the store is the historic “Red Room,” adorned with 3 million hand-painted tiles, now showcasing an extensive shoe collection. Printemps New York aims to offer an immersive shopping experience, integrating fashion, dining, and cultural events to create a dynamic community hub. When I tell you I’m obsessed, it doesn’t fully explain it!

Watch my first visit:

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 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!

She is here until May 4th and of course tickets fly. This is an artist the kids love! Expect an unforgettable night as she takes the stage, blending futuristic sounds with her signature bold presence. This also makes for an awesome birthday gift.

Experience the vibrant world of Vincent van Gogh at the New York Botanical Garden’s Van Gogh’s Flowers exhibition, running from May 24th through October 26th. This immersive showcase features stunning botanical displays alongside contemporary art installations by artists such as Lee Baker and Catherine Borowski, allowing visitors to walk through fields of real and sculptural sunflowers that echo Van Gogh’s iconic works. Enhance your visit with special events like the LEGO® Botanical Garden Pop-Up, plein-air painting sessions and Starry Nights. The evening experiences are complete with live music, performers, and a dazzling drone show inspired by The Starry Night.

Fleet Week

Fleet Week is back! It’s an exciting showcase of naval tradition, history and pride, with ships, aircrafts and sailors from around the world arriving in New York City. You can look forward to tours of majestic vessels, thrilling airshows, and unique events that celebrate the nation’s military service members. This is taking place the 21st-27th and a great way to kick off Memorial Day Weekend.

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. Starting this summer, you can enjoy a serene waterfront escape with stunning views of the East River and the iconic skyline. This picturesque spot combines relaxing outdoor dining, seasonal events, and an inviting atmosphere, making it a perfect destination for both locals and tourists looking to unwind. It opens up on the third of this month and is a great place to go with friends and get not only the best views but amazing drinks and bites.

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.

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!

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!

Located at Brooklyn Bridge Park, May 3rd is Jane’s Carousel Day! From 11AM-5:50PM, you can get face painting and free rides all day. This is a great family-friendly activity and the kids love it.

Head over to Queen’s County Farm Museum for their Apple Blossom Carnival. Taking place May 3rd-4th and 10th-11th, you can ride rides, play games, check out local food vendors, see farm animals and so much more. Tickets are available now!

Pier 5 is holding a kite festival! On May 17th from 11AM-3PM, bring your kite and have yourself a day! This is actually the only day there is open to the public to fly kites in the city and it’s the best spot to do it.

Manhattanhenge

Manhattanhenge is a biannual event when the setting sun aligns perfectly with the east to west streets of Manhattan’s grid, creating a striking visual between the city’s skyscrapers. It typically occurs in late May and mid-July, drawing crowds eager to capture the glowing sunset framed by urban architecture. This May it will be visible the 28th-29th.

The Dumbo Drop is an annual community fundraiser in Brooklyn’s DUMBO neighborhood, where thousands of toy elephants equipped with parachutes are released from rooftops onto Washington Street. This amazing event supports local Title 1 public schools: PS 307 Elementary and The Dock Street Middle School and features a vibrant block party with live music, kids’ activities and local food vendors. You can check it out on May 30th.

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!

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 17th-18th, 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 11th 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!

Loews Regency New York Hotel is celebrating Spring and Mother’s Day with a weekend full of fashion, florals, and delicious food from Friday, May 9 to Sunday, May 11. The hotel is offering a thoughtfully curated lineup of experiences, including a Floral Cart by Patrick J. Clayton Productions, a classic Mother’s Day brunch at The Regency Bar & Grill, and a pop-up shopping experience with Zadig & Voltaire, offering luxury items for the perfect Mother’s Day gift. Guests and locals alike can enjoy these exclusive offerings, which highlight the best of springtime in Manhattan while celebrating the special women in our lives.

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. It’s happening in NYC throughout the month.

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!

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!

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!

On May 18th, 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, walk or just donate if you are unable to make it that day!

CityPickle is back at the Wollman Rink!. With 14 state-of-the-art courts ready for play, reservations will be available daily from 8AM- 9PM. This season will feature expanded kids’ programming, private event spaces, coaching sessions, and open play, making it even better than before. They also have an after school program every Tuesday this month, where 3rd-8th graders can make friends, learn about pickleball and have the best time! Check out their camp programs too if you are looking for options.

Baseball season is officially in session! The New York Yankees and Mets have tons of games and we think there’s no better way to spend a spring day than cheering on your favorite team. Whether you’re a die-hard fan or just looking for a fun day out with family or friends, a visit to the ballpark is a classic NYC experience.