Westchester Daters: You Need To Go On The Best Westchester Dates

A few weeks ago, we gave you the comprehensive list of where to go on a date in NYC. Now: where to go on a date in Westchester!

Westchester covers a lot of area, and our dates do too — both in location and activity type. This list of the best Westchester dates is built entirely from trusted recommendations from our Westchester-based friends (not from sponsorships or those impersonal “Top 10” lists), so anywhere you choose, we can guarantee a top notch date 😊

Goosefeather in Tarrytown

Westchester Dinner Dates (or Drinks at the Bar)

The Inn at Pound Ridge (Pound Ridge)
Ultra romantic cozy cabin vibes at this sleek spot.

Cenadou (North Salem)
Bright and quaint modern French bistro, with an attached cocktail bar and outdoor lounge.

North Star (Pound Ridge)
Rustic New American. Bring your date to their live music every Thursday!

Town House (New Rochelle)
Town House was just added to the Michelin Guide in 2023, and the head bartender from Blue Hill at Stone Barns crafted the cocktail menu (which is to say… they’re really, really good).

Goosefeather (Tarrytown)
Top Chef’s Dale Talde brings Cantonese food to Westchester in a modern parlor setting with a whimsical flair.

Tipsy Taco Bar (Scarsdale)
Because some of the best dates are when you share chips and guac (and multiple margaritas) at a cute low-key Mexican joint.

Dubrovnik (New Rochelle)
Michelin Guide recommended Croatian restaurant with a backyard that fully transports you to the Mediterranean.

Sergio’s (Pelham)
Classic old-school Italian. Even if you’re not up for a big pasta dinner, go for a glass of wine and their magnificent desserts. The Napoleon is a work of art!

The Wooden Spoon (New Rochelle)
Sometimes you need a burger and a beer, and you need them both to be really tasty. Outdoor patio open for summer dates!

Moderne Barn (Armonk)
New American in a wood-paneled 2-story interior that gives major ski chalet vibes.

Empire State Trail

Westchester Activity Dates

Ward Pound Ridge Reservation (Pound Ridge)
Beautiful woodsy hikes of a multitude of lengths and difficulties. You can check out the top-rated ones on AllTrails here.

Empire State Trail
A 750-mile-long trail that’s mostly flat, so it’s perfect for biking. The best part is that it runs near the Amtrak line, so you can bike between towns and train back when you’ve had enough (but we recommend stopping for an ice cream or a beer first!).

Katonah Museum of Art (Katonah)
An eclectic collection of visual art across cultures and time periods. Always endless things to discuss on a museum date!

Caramoor Center for Music (Katonah)
Year-round concerts across genres in their intimate concert hall, plus outdoor concerts throughout the summer.

Jacob Burns Film Center (Pleasantville)
You can’t beat a classic movie date, sharing a bucket of popcorn between the two of you. Jacob Burns has all the latest movies, plus tons of special events, like classic movie film series and Q&As with directors. We recommend grabbing great BBQ at Southern Table Kitchen beforehand.

Zwilling Cooking Studio (Pleasantville)
Cooking is already a romantic activity – add some fun by taking a cooking class together. Use it as an opportunity to see how well you collaborate… or to show off your skills.

Have other Westchester recommendations? Have another city in mind for a date list? Let us know!

Happy Dating,


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