A collage of images: a couple at a spa, an orchestra on stage, glass beer bottles clinking, and a couple holding hands on the beach at sunset

12 Exciting Westchester Date Ideas

Whether you’ve been together for 2 months or 20 years, date night is important. No matter what your interests are, there’s plenty to do locally. Here are 12 of our favorite date ideas in Westchester County.

Couple toasting in the sunset

For a Lively Date

Check Out a Brewery

Captain Lawrence Brewing Company – Elmsford

If you and your date are looking for good food and great drinks in an energetic community setting, check out Captain Lawrence Brewing Company. Located a short drive off the Sprain Brook Parkway, this brewery makes for a lively Westchester date night. CL boasts of a 2500 square foot beer hall and a 6000 square foot outdoor beer garden. They produce a wide range of beers, from pale ales to NEIPAs, with names like Freshchester and Imperial “Rye”der (a pumpkin ale sporting the Headless Horseman) to pay homage to their NY roots. They also hold plenty of events like trivia on Wednesdays and live music on the weekends.

For the adventurous outdoorsy couples, Gotham Bicycle Tours even offer day rides to the brewery from May to October. Riders take a scenic 35 mile trip from Brewster along the Empire State Trail, ending with lunch at the brewery. They then offer train ride back up north. No buzzed biking here in Westchester!

couple bike riding in Westchester

For a Historical Westchester Date

Take a Historical Bike Tour

Tarrytown Lakes Trail – Tarrytown

Can’t decide if you and your date want to take in nature, explore the historic Hudson Valley, or grab a bite to eat? Why not do all three? Take exit 23 on the Saw Mill River Parkway and park at the Neperan Road-Tarrytown Lakes lot. From there you can leisurely bike along the Tarrytown Reservoir, which is also a great spot for bird watching. The trail connects to the Andre Brook Trail, which will take you into Sleepy Hollow, a town steeped in history. Its most famous spots include the Old Dutch Church and cemetery, the setting for the Washington Irving tale; Philipsburg Manor, a living colonial museum where you can learn about the daily life of 23 enslaved Africans who inhabited the mill; and Kykuit, the opulent Rockefeller estate. Please note that the latter two requires tickets from the Historic Hudson Valley to visit. From there, you can take the Old Croton Aqueduct Trail into Tarrytown and sample the local cuisine. You can’t go wrong with any of the establishments on Main Street.

Couple looking at art in museum.

For a Nerdy Date

Stroll Through a Museum

Hudson River Museum – Yonkers

The Hudson River Museum is another one of our Westchester date night ideas. Perfect for a fun and educational indoor date, for art and science lovers alike. You can stroll through their varied galleries that spotlight artists from around the world, both past and present. Their collection of Hudson River School artists is especially impressive. One fun permanent feature is Red Grooms’ “The Bookstore”, described as a sculpto-pictorama that invites visitors to explore and be a part of the work. If science is more your speed, visit the Hudson Riverama, an interactive exhibit that teaches visitors all about the history and ecology of the Hudson River. On the weekends, you can grab tickets to the planetarium and listen to live lectures as you star gaze. During the summer, the HRM holds a Summer Amphitheater Series, featuring live music, plays, and even falconry overlooking the Palisades. Be sure to check their calendar of events for interactive workshops as well.

Couple hiking on trail

For a Challenging Outdoor Date

Go for a Hike

Bull Hill Trail – Cold Spring

For the outdoorsy pair who are up for a challenge, Bull Hill is the spot for you. Although not as challenging as Breakneck Ridge, which is just a mile away, it’s a decent climb that still leaves you with enough breath to talk to your partner. Also known as Mount Taurus, it reaches an elevation of 1500 feet at its peak. Depending on the loop you choose, it should take 2 – 4 hours to complete the circuit. Along the way you’ll find prime spots to view the rest of the Hudson Highlands State Park Preserve. A few notable landmarks are Crow’s Nest and Storm King Mountain across the river. One other feature of the trail are the Cornish Estate ruins, the remnants of a mansion built in 1910 but destroyed in a fire and abandoned in 1958. After coming down from the mountain, you can rest on the sandy beach of Little Stony Point, located just across the street. 

Couple running on beach.

For Fun in the Sun

Bask on the Beach

Croton Point Park – Croton-on-Hudson

No need to drive all the way to the Jersey Shore if you’re looking for a beach trip. Croton Point Park, located right by the Croton-Harmon MTA station, is a 508-acre nature getaway maintained by Westchester County. With lifeguards on duty and water quality monitored by Riverkeeper, it’s a safe and clean environment. When you’re done taking a dip, there’s plenty more to do. The park also features boat and kayak rentals, camp grounds, baseball and soccer fields, a remote control aircraft field, picnic areas, and a nature center to learn about local flora and fauna. Be sure to check the calendar to catch their weekly events, with topics like archaeology and survival skills. We know how important your dogs are to you, so you’ll be happy to know that dogs are welcome!  

Couple having a spa day

For a Relaxing Date

Get a Massage

Spavia Day Spa – Thornwood

Giving your partner a massage after a long day is a great way to connect, but sometimes you just need a professional. Spavia provides a wide range of treatments, so you’re both sure to find the perfect one for your needs. Whether you’re looking for a deep tissue massage, a facial, or a body wrap, they’ve got you covered. There are even treatments specifically targeted for men. Or if you want a sense of togetherness, couples massages are available. The facilities are clean and include separate men’s and women’s locker room/shower areas. They also have a lounge where you and your loved one can sip tea and take a moment to soak in each other’s company after your treatment.

Cooking together in kitchen

For a Foodie Date

Learn How to Cook

Sur la Table – White Plains

Something about cooking together is romantic. Don’t believe me? Look at Hallmark’s movie list. The act of creating something together promotes a sense of unity, and making something nourishing for your partner is an act of love. Whether you’re a novice or a seasoned chef, Sur la Table offers great hands-on cooking classes for all skill levels and palates. From Tuscan chicken to Japanese sushi to French pastries, it’s easy to find a class that calls to you. A professional chef will guide you through the 2 hour process. You’ll leave with skills and confidence so you can keep getting cozy in the kitchen.

Couple painting together

For an Artsy Date

Paint Pottery

A Maze In Pottery – Briarcliff Manor

A Maze In Pottery has been the setting for lots of happy dates for over a decade. This paint your own pottery studio carries over 500 bisque items ready for your artistic touch. After choosing your piece—anything from mugs, cookie jars, picture frames, to animal figurines—you’re given supplies and glazes and unlimited time to work. They’ll fire it when you’re done and in a few days you can return to pick up your masterpiece. If the thought of painting anything you want overwhelms you, you can also sign up for their paint night events. They are BYOB and an instructor will lead you step by step in creating a finished piece. Either one you choose, it’s a perfect way to create a keepsake of your time together.

Couple in movie theater laughing

For an Intellectual Date

Catch an Indie Film

Jacob Burns Film Center – Pleasantville

Going to the movies is a classic Westchester date night idea. The Jacob Burns Film Center is a special treat for film nerds. The JBFC is a nonprofit cinema and education center. Sure, they play current movies, but they also promote documentaries, independent, and foreign films that don’t get as much attention from larger theaters. For lovers of the classics, they also present Golden Age gems on 35mm. As promoters of visual literacy, they often hold screenings followed by Q&A sessions with the filmmakers, providing a more intimate engagement with the medium. If you’re looking for a date night activity that will spark thoughtful dialogue between you and your partner, the JBFC is a sure bet.

Concert with couples outdoors

For a Classy Date

Listen to Live Music

Caramoor Center for Music and the Arts – Katonah

Music lovers will feel right at home at the Caramoor Center for Music and the Arts. The Caramoor has a long and fascinating history, beginning as a home for the Rosen family, outspoken patrons of the arts. They later converted it into a public venue. The picturesque Renaissance estate has provided the perfect backdrop for classy concerts of all genres for over 75 years. Every act from orchestral, to chamber, to opera, and gospel has played on the grounds. During the summer they hold a large American Roots open air festival. Their calendar also highlights afternoon tea in the music room, and swing dancing—a perfect couples activity.

Couple zip-lining over a farm

For an Adventurous Date

Swing Through the Trees – Zipline

Boundless Adventures – Purchase

Active couples looking for an adrenaline rush can find it at Boundless Adventures, an aerial adventure park located on Purchase College campus. Upon arriving you’re given a safety briefing. Then you have three hours to explore the park’s 12 courses, which consist of obstacles such as cargo net ladders, rotating log bridges, rock walls, auto-repel drops, and ziplines. They even hold themed “Glow in the Park” night climbing events, where the course is decked out in neon lights. Nothing forges bonds better than pushing your boundaries together.

Couple hugging at amusement park

For a Fun & Nostalgic Westchester Date

Play at a Carnival

Playland – Rye

It might seem cliche, but a carnival date is still lots of fun. An especially great Westchester date spot is Playland in Rye. Open since 1928, it’s been designated a National Historic Landmark. While they’ve kept some of the original rides like the Dragon Coaster and the Grand Carousel, they’ve made plenty of new and exciting additions. If thrill rides are your thing, check out the Crazy Mouse coaster, the Double Shot, and the Playland Plunge, the amped up version of the classic Log Flume. If sun and sea are more your vibe, you can grab passes to either the pool or their sandy beach along the Long Island Sound. Of course, don’t forget to hit the arcade and midway games to try your hand at winning your beloved a prize.

A Westchester Date Can’t Be Beat

With so much to do in Westchester County, your weekend plans will never be dull. And if you’re a couple discerning marriage and you’re ready to take the next step in your journey towards forever, reach out to us! We’ve got some great advice on engagement shoots, and openings to capture the love between you.