New York City is always buzzing with something fun around every corner, no matter what day, month, or time of the year it is. Why not use this eclectic mix of activities for planning dates that match the mood that every season brings along? Spring in the air and in your step? Soak up the blossoms and the beauty of the skyline. Feeling the winter chill in your bones? Look for something cozy to do with your bae. In this article, we’ll walk you through the best ideas for dates in NYC, for every time of year, along with tips on how to prepare and dress to kill for each of these dates, so you look and feel great.
Season-by-Season Date Planner for NYC
New York changes radically with the seasons, and as a local, you know the city’s magic really comes alive when you step outside your routine. Each season brings unique activities: picture yourself strolling under pink cherry trees in spring, catching a free movie in a summer park, crunching leaves on a fall walking tour, or gliding hand-in-hand on an ice rink in winter. Those right there are some of the most romantic things to do in New York.
So, turn these seasonal offerings into the playbook for planning the most soul-stirring dates in NYC. Whether you’re looking for something splurge-worthy or free/cheap dates in New York, we’ve got you covered.
Spring dates in NYC (March–May)
As New York thaws back to life, come spring, it’s time to infuse fresh energy into your dating life as well. Here are some fun ideas for planning dates in NYC in the spring season:
1. Soak up the Cherry blossoms at the Brooklyn Botanic Garden (Brooklyn)
Wander through the Sakura-rich gardens when pink blossoms peak. The Cherry Esplanade and Japanese Hill-and-Pond Garden have an inherently magical vibe that makes it the perfect spot for spending some mushy moments with your partner. To top up with some fun, catch the Sakura Matsuri festival in April for live Japanese music and tea ceremonies.
2. Picnic at Central Park’s Cherry Hill (Manhattan)
Meet under the Yoshino cherry trees around 72nd St (near the lake) for a peaceful picnic. The trees form a pastel canopy, and Bow Bridge is right there for a stroll. Totally free—just pack some snacks and a blanket for this classic spring vibe. Pro Tip: Go early to beat the crowds.
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3. Roosevelt Island Cherry blossom walk (Manhattan)
Cherry blossoms are truly the highlight of New York in spring, and so, integral to planning the most magical dates in NYC during this season. Take the Roosevelt Island Tram over to the island. An East River promenade is lined with cherry trees and offers a great Manhattan skyline backdrop. No admission fee, and less crowded than Central Park. Bonus: There’s an annual cherry blossom festival here with music and food.
4. Randall’s Island Cherry Grove (Harlem River)
Looking for offbeat things for couples to do in New York? Check out this hidden gem: the Cherry Blossom Grove, along the water. It’s usually quiet, so you and your date can enjoy some quality time together, admiring the pink and white blooms in peace. Pro Tip: Pack a lightweight windbreaker since island breezes can be cool.
5. New York Botanical Garden (Bronx)
Besides spring blooms, NYBG hosts seasonal exhibits and tulip shows. The Cherry Tree Collection on the Oswald Dillon Memorial Plaza is stunning this time of year. You’ll see not just cherries but magnolias and azaleas. This is one of the best date ideas NYC during the spring for anyone who loves flowers.
6. Riverside Park Cherry Trees (Manhattan)
Walk the Hudson River Greenway up by 100th St, lined with Japan-gifted cherry trees dating back to 1912. A tunnel of pink blossoms appears around mid-April. The vibe is especially romantic at sunset. Afterwards, you can grab pizza in the neighborhood or coffee in nearby Upper West Side cafes.
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7. Smorgasburg Food Market (Brooklyn/Manhattan)
This date planner isn’t all about parks and blossoms. We think hitting a food market is another perfect spring date idea. Sample dozens of cuisines while strolling under the warm sun. Smorgasburg is free to enter and runs Fri–Sun—Fridays in Manhattan’s Oculus, Saturdays in Williamsburg (90 Kent Ave), and Sundays in Prospect Park’s Breeze Hill.
8. Free Kayaking on the Hudson (Manhattan)
Start from Pier 96 in Hudson River Park and paddle your way through the majestic river. Manhattan Community Boathouse offers life jackets and kayaks from May through October. The view of the skyline from the water is unbeatable, and you can usually slide in without a reservation. You see, planning a fun date with a healthy mix of adventure and romance isn’t that hard, especially in a city like New York.
9. Staten Island Chinese Scholar’s Garden (Staten Island)
This serene garden inside Snug Harbor is modeled on a Ming dynasty design. You can wander among ponds and pavilions and feed the fish—free koi fish feeding included. Spend about an hour here, and then follow up with a ferry ride (also free) into a cozy dinner back in Manhattan or Brooklyn.
10. Brooklyn Bridge Park Stroller Tour (Brooklyn)
Stroll the waterfront park under blooming cherry trees near Fulton Ferry Landing and Pebble Beach. No fee to enter the park. Along the way, you can swing by Jane’s Carousel or chill on the concrete beach. It’s a favorite local spot for photos of Spring leaves framing the skyline.
Bonus: If you’re looking for something extravagant, book a CitySightsNY tour afterwards for an aerial view of the city in bloom.
How to prepare for spring dates in NYC
So, the date is finalized. You have a place and time in place. Now comes the part about getting ready for the day. Of course, you want to dress to impress, but it’s equally important to keep your comfort in mind and step out prepared to enjoy the activity you have lined up. Here’s how:
- Dress in layers: Spring in NYC can be unpredictable. It might be 60°F in the morning and 80°F by afternoon. Bring a light jacket or sweater that you can tie around your waist if it warms up. Flowering trees and river breezes can be chilly early on
- Bring an umbrella or rain jacket: April showers are real. A compact umbrella in your bag can save the day (and your date). If it rains, you can duck into museums or cozy cafes without missing the fun
- Pack picnic essentials: For park dates, grab a blanket and snacks ahead of time. Bring a picnic tote or insulated lunch bag to keep food fresh
- Keep your look fresh and natural: For lighter spring makeup, try Milk Makeup’s Dewy Serum Concealer for a subtle glow that doesn’t weigh your skin down in warmer weather. Don’t forget SPF in your moisturizer or primer (even on cloudy days).
- Comfortable shoes are a must: You’ll likely walk a lot under cherry trees or across parks. Style up your outfit with a chic pair of sneakers or flats—you can look polished without sore feet.
Outfit ideas
Now, let’s get to the specifics of what to wear on your spring dates in NYC. Here are some ideas:
Summer dates in NYC (June–August)
Channelize the warmth in the air into your dating life with these romantic things to do in New York during the summer:
1. Coney Island Beach & Boardwalk (Brooklyn)
Spend a day at the iconic seaside. Walk the boardwalk hand-in-hand, sunbathe on the sand, or ride the famous Deno’s Wonder Wheel for sunset views. The beach itself is free, though you can rent a blanket or bike on site. Don’t miss grabbing Nathan’s hot dogs or cotton candy
2. Brooklyn Cyclones Baseball Game (Brooklyn)
Catch a minor-league game at Maimonides Park (Coney Island). It’s fun and affordable—perfect for those looking for exciting yet cheap dates in New York. Games often have giveaways and Friday-night fireworks. Enjoy nachos and ice cream in the stands; the view of the boardwalk from the bleachers makes it a unique ballpark date
3. Little Island concert or picnic (Manhattan)
This quirky new Hudson River park opens in summer with 70+ free performances—music, dance, theater—each week. Entry to the park is free, and events are ticketed, usually $25. Even without a show, the sloping green hills are great for a sunset picnic with skyline views. It’s a fresh, artsy spot for a date.
4. Bryant Park Movie Nights (Midtown Manhattan)
On summer Mondays (June–Aug), the free films are screened on Bryant Park lawns starting at 8 pm. Weather permitting, you’ll watch classics under the stars. One of the most romantic things for couples to do in New York. Pro tip: Blankets go out early (lawn opens at 5 pm). So get there on time, grab coffee or frozen drinks nearby.
5. Governors Island outing (Brooklyn)
Take the NYC Ferry or book a CitySightsNY ride, if you’re looking for an extravagant touch to the experience, to Governors Island on a summer weekend. Over 120 acres of lawns, forts, and public art await. Rent bikes or grab something to eat at one of the food stands, talk, laugh, walk about, and connect, miles away from the city hustle.
6. Hop-On Hop-Off bus tour (Citywide)
Yes, it’s touristy, but it’s a fun way to sightsee with your date. CitySightsNY runs a Big Bus Downtown 24-hour pass that loops through Manhattan. You can sit upstairs for panoramic views of landmarks like the 9/11 Memorial or Times Square, hopping off for quick detours. The live guide will point out hidden facts and photo-ops. This is one of the best date ideas NYC for people who are new to the city.
7. Harbor Lights Night Cruise (Manhattan/Brooklyn)
Book a CitySightsNY evening cruise to see the skyline sparkle from the water. You can choose from a fast speedboat or a classic sail under the stars to glide by the Statue of Liberty and the Brooklyn Bridge illuminated at night. Many cruises offer a drink bar on board, or you can simply snuggle up on deck.
8. Bryant Park Picnic Performances (Midtown Manhattan)
Planning a fun date that is easy on the pocket? Check out the free summer series of live music, dance, and theater every Monday (and some Fridays) in Bryant Park. Genres range from jazz to contemporary dance. Spread a blanket on the lawn and enjoy these shows. It’s like a mini-festival atmosphere in the heart of the city.
9. Enjoy a movie with a view (Brooklyn)
Each Thursday in July–Aug, Brooklyn Bridge Park’s Pier 1 shows free films at sunset. Pack snacks or grab takeout on the way, then relax on the grass with Manhattan’s skyline behind you. Films range from new releases to family classics. The evening breeze off the river and the lit-up skyline make it especially magical.
10. Summer rooftop movie at Pier 17 (Manhattan)
Head to the Seaport’s Pier 17 for a free movie on the rooftop. Doors open at 5 pm, movie at 7:30. You must RSVP online, but it’s first-come, first-served. Bring a blanket or rent a chair. Before or after the film, explore Seaport shops or grab pizza at Quality Italian downstairs.
Related Reading: Step-by-Step Guide to Crafting an Irresistible Dating Profile for NYC Singles
How to prepare for summer dates in NYC
Having the perfect summer dates in NYC entails more than just zeroing in on the right place and experience. Here are some things to keep in mind to make sure your lack of preparation doesn’t chip away at your time together:
- Stay cool and sun-protected: Summer can be brutally hot. Wear lightweight, breathable fabrics like cotton or linen. Apply sunscreen on dates that involve parks or boat rides. Try a tinted sunscreen or Milk Makeup’s Liquid Strobe for a soft glow, plus SPF. Don’t forget a hat or shades if you’re walking
- Hydrate and plan indoor backups: Carry a refillable water bottle. If temps spike above 90°F, have a plan B, like catching a museum or grabbing an iced coffee break. Check out happy hour or drink specials at nearby cafes so you can cool off without breaking the bank
- Dress for both day and night: Mornings can be hot, and evenings are surprisingly cool by the water. A light cardigan or denim jacket over a dress or over a T-shirt for guys can handle shifting temps. Pack a shawl or sports coat in your bag if you’ll be dining al fresco after sunset
- Comfortable yet stylish shoes: With so much walking involved in most summer date plans, you’ll need chic sandals or low-top sneakers that look good with shorts or dresses. You’ll be happier in footwear that you trust for 10k+ steps
- Go with the festive vibe: Consider light shimmer makeup, a bold lip color, and Milk Makeup’s Blur Stick is great for fending off sweat. For guys, a neat but casual button-down looks sharp but stays breezy. Remember, layer a pop of color into your outfit (bright scarf or tie) to capture that summertime energy.
Outfit ideas
Here’s how to channel the summer vibe in your date outfits
Bonus Tip: Try a Summer White look—white tees and denim for him, a white cotton skirt and tank for her—complemented by pops of color (a bright scarf or fun floral pattern)
Autumn dates in NYC (September–November)
The auburn hues of autumn bring with them a magical charm that not only elevates the vibe of the city but can also uplift your dating life. Here are some of the best date ideas NYC for autumn:
1. Wave Hill Public Garden (Bronx)
A 28-acre riverside garden that’s gorgeous in fall. Admission is $10 for adults and completely free on Thursday evenings. Walk the terraces and woodland paths to see vibrant maples and ginkgo trees against the Hudson River view. There’s a cozy art gallery cafe on-site too—a perfect spot for cider or hot cocoa afterward.
2. Queens County Farm pumpkin patch (Queens)
The city’s working farm has a huge pumpkin patch in October, which is open daily late Sept–Oct. Why not turn your Halloween preparations into a fun date with your bae? You can also pet goats and visit the horse stables. It’s like a quick escape to the country. Along with a giant pumpkin, don’t forget to pick up some apple cider donuts to go.
3. City Lights River Cruise (Manhattan)
Catch an early evening Circle Line or CitySightsNY cruise to see fall colors reflected in the water and skyline lights at dusk. These cruises often include onboard narration. A cruise departs Pier 83 in Midtown; the cool breeze and lit-up landmarks make it very romantic.
4. Central Park Fall Foliage Walk (Manhattan)
The heart of NYC bursts into color by late October. Wander The Ramble, the Reservoir, or Sheep Meadow when oaks and elms turn gold. Snap a leaf-pile photo by the Bow Bridge or row a boat under a canopy of red and orange. See how effortless planning a fun date in NYC can be!
5. Bryant Park Winter Village preview (Manhattan)
Starting late October, the Winter Village (holiday market) opens at Bryant Park, along with the ice rink. Head there for your date, and spend time browsing hundreds of vendors selling crafts and snacks, try the truffle fries or hot spiced wine at The Lodge. This festive setup is an early teaser for winter.
6. New York Botanical Garden holiday train show (Bronx)
Beginning in mid-November, tiny model trains weave through replicas of NYC landmarks made of plants. See the Waldorf-Astoria, Statue of Liberty, and more — all with a train whistling around. Inside the conservatory, it’s warm and holiday-decorated, making for a merry date.
7. Prospect Park movie night (Brooklyn)
On the first Friday of Sept and select dates, Prospect Park hosts outdoor movies for free. It’s like Bryant Park’s film series but in Brooklyn’s backyard. Post-film, explore nearby Park Slope eateries and grab a pizza or drinks, and you have one of the most low-key yet perfect dates in NYC.
8. Roosevelt Island Tram ride (Manhattan)
Take the Roosevelt Island Tram at dusk for 360° skyline views. Once on the island, stroll the waterfront or grab a bite at Mercado Little Spain, a Spanish food hall. Fall sunsets are incredible from there. Bonus: it’s usually less crowded on weekdays.
9. High Line art stroll (Manhattan)
The elevated park on the West Side showcases fall plantings and street art. Walk from Gansevoort St northward as the setting sun lights up the Hudson Yards architecture. You might pass pop-up yoga classes or dance performances on the Plaza. End at Chelsea Market to warm up with coffee.
10. Edge at Hudson Yards (Manhattan)
In search of dates in NYC? Head 1,100 feet up to NYC’s highest outdoor sky deck. Tickets are about $40. The wraparound glass wall offers a vantage over fall foliage in Central Park and the Empire State. Go just before sunset. Afterward, you can toast with cocktails back on ground level.
Related Reading: NYC Relationship Roadmap: Milestones from First Date to Moving In
How to prepare for autumn dates in NYC
Get the basics right so that nothing gets in the way of you having fun and truly connecting with your date
- Layer up and stay dry: Autumn mornings and evenings get cool quickly. Pack a light sweater or scarf, and maybe a raincoat. Check the weather — if it calls for rain, plan a backup indoor spot like a cozy cafe or museum.
- Comfortable shoes for leaf-peeping: You’ll likely be walking through parks or markets. Now is the time for stylish boots or sturdy sneakers
- All about rich colors: Autumn is a great season for richer colors. Women can reach for a berry lipstick or gold eye cream, Milk Makeup Gloss is fun for sparkle. Men can wear a warm cashmere scarf or wool cap. Layers in burgundy or forest green look great in photos with fall leaves
- Plan well: By late fall, the sun sets as early as 5 pm. If you’re aiming for a sunset date, check the exact time online. For evening dates, bring a travel flashlight app or headlamp just in case (NYC parks are mostly lit, but it’s nice to have). And if it’s Halloween season, check if anything special is happening, like NYC’s iconic Village Halloween Parade in late Oct)
Outfit ideas
Crush it with these spectacular outfits:
Winter dates in NYC (December–February)
Don’t let the chill in the air dampen your dating life. There are plenty of great dates in NYC you can explore even in the thick of winter. Here are our top picks:
1. Bryant Park winter village (Midtown Manhattan)
This is NYC’s famous holiday scene. The ice skating rink is open, and surrounding you are over 150 winter huts selling hot cider, artisan chocolates, knits, and crafts. The holiday lights and festive music make the date feel straight out of a movie. Warm up at “The Lodge” beer garden with a hot toddy.
2. Rockefeller Center Ice Rink (Manhattan)
Skating in front of the giant Christmas tree is quintessentially NYC and but going here once is a rite of passage. Even watching from the side (and sipping cocoa at the nearby Plaza) is magical. Make a date of it and enjoy the experience to the fullest
3. Holiday markets (Manhattan/Brooklyn)
Aside from Bryant Park, check the markets at Union Square and Columbus Circle. Window shop for artisanal gifts in a festive atmosphere. Stock up on unique NY gifts like NYC-themed ornaments or cozy wool hats. Many vendors give small discounts if you say a secret password (gotcha – just kidding!).
4. The Met Fifth Avenue (Manhattan)
The main Met’s rotunda is decorated for the holidays, and upstairs you can find seasonal exhibitions. The Met is very quiet in winter, plus, it’s warm inside and HUGE, great for getting lost together among art. Easily one of the best date ideas NYC during those chilling winter months.
5. Chinese Scholar’s Garden (Staten Island)
This serene spot remains open through the winter. The bare trees reflecting in the ponds have their own quiet beauty. Afterward, warm up with a Chinese lunch in Snug Harbor or head back to Manhattan for dumplings. If there’s snow, the garden looks like a scene straight from a storybook, making a trip here one of the most romantic things for couples to do in New York
6. NY Botanical Garden holiday train show (Bronx)
Extending into winter from mid-November, this is a real fairy tale with twinkling lights. It’s worth visiting in early winter too. If you missed it in fall, go now—the gardens are fully decorated with lights and the model trains wind around the Conservatory.
7. Holiday lights tour (Citywide)
Book your CitySightsNY ride for a guided evening through NYC’s brightest spots —the Rockefeller tree, Saks windows, and Dyker Heights lights. Tours run Nov–Jan. They often include mulled wine or hot chocolate. A cozy date that will surely make you two feel closer and more connected, as you lean in and soak up the magic of millions of twinkling lights passing by. Check CitySightsNY’s site for schedules — it’s a flexible, warm way to see the city.
8. Harlem Gospel Brunch (Manhattan)
On Sundays, attend a lively gospel brunch at a Harlem soul food spot. Many places have great music on Sundays, and it’s a cultural staple in winter when strolling might be too cold
9. A city winery or spa date
When temperatures drop below freezing, indoor dates in NYC become the norm. If you’re a thrill seeker, this can be a visit to NYC’s indoor ski simulators. But if you’re looking for something more laid back yet romantic, a wine tasting at City Winery (NYC) or a couple’s massage at a Midtown spa works best.
Related Reading: Navigating Exclusivity In A Relationship: How to Do It Right
10. Staten Island Ferry Round Trip
It’s free, and winter on the water has crisp views of the Statue of Liberty, Battery Park, and NYC’s skyline at twilight. Take it after sunset and admire the city lights. Bring a travel mug and enjoy a hot coffee as you speed across the harbor. The ride is only 25 minutes one way and is truly romantic on a cold evening (layers and a beanie recommended)
How to prepare for winter dates in NYC
You cannot expect to just step out and wing it in the harsh NYC winter. Preparation is key
- Bundle up smartly: NYC winters can go below freezing, so dress in thermal layers: a wool coat, gloves, a hat, and a scarf. For glam looks, wear a faux-fur or down coat. If you’ll be outdoors a lot, waterproof boots are your best friend.
- Warm drinks and snacks: Plan for coffee breaks or warming cocktails in cozy cafes or bars with fireplaces. Many Manhattan bars offer festive cocktails like mulled wine or Irish coffee, which can really warm you up
- Time it right: Early January can be super quiet in the city, but late Nov–Dec is jam-packed. If you hate crowds, aim for a winter date in January when lines are shorter and restaurants are easier to book. In Nov–Dec, make reservations if possible, even calling a day ahead
- Festive grooming: Winter light is low, so a little glow on your face can brighten things up. A shimmery Milk Makeup Matcha Dewy Oil Tint or highlighter stick will catch soft light.
- Comfort equals confidence: If you know your feet will get wet or cold, wear warm insoles or socks. For women, a dress with thermal tights or leggings can look fancy while keeping you warm. For men, a thick sweater under that blazer or a classy scarf really dresses up the outfit and keeps the chill out.
Outfit ideas
Warm up your date’s heart with these killer outfits:
Takeaway
Regardless of the season, NYC offers endless adventures. The key to turning these into memorable dates in NYC is timing it right and dressing for the weather. With these ideas and tips, you’ll be ready for a year’s worth of fun, unique dates across all five boroughs. Enjoy every moment of the season and each other’s company — the city itself will do the rest!