Things to Do in Westchester County for Couples: 8 Date Ideas for Different Moods

For couples, the best things to do in Westchester County mix something lively with a good meal. These date ideas range from a concert or long dinner to an active afternoon or a late-night out.

1. See a Concert, a Jazz Set or a Film

For a date night in Westchester, start with The Capitol Theatre in Port Chester, which has the biggest concert room in this guide. It opened in 1926 and seats about 1,800 people. Garcia’s, the bar next door, hosts local and national bands weekly.

If nothing at the Capitol suits you, try one of these:

• Jazz Forum ranks among the liveliest things to do in Tarrytown, with live jazz from Friday to Sunday. Choose it if you want dinner and music in one place, since the club serves food during the show.
• If you would rather laugh than listen, Tarrytown Music Hall stages musicians and comedians in a building that dates to 1885.
• For a film instead, Jacob Burns Film Center in Pleasantville shows independent, foreign, and documentary films. Its wine bar opens from Thursday to Sunday.

2. Dress Up for a Long Dinner

Blue Hill at Stone Barns is the choice when the dinner is the whole event. Among romantic restaurants in Westchester, it is one of the most formal. It has no menus and serves one long multi-taste meal for more than $450 per guest.

For a less formal meal, these three work well:

• The Yonkers City Pier is home to The Sea Fire Grill, which serves contemporary American seafood with wide views of the Hudson.
• Red Hat on the River in Irvington adds a rooftop bar for a drink outside first. Nearly every seat looks out on the water.
• On selected Fridays, Red Horse by David Burke in White Plains hosts comedy nights with a three-course dinner.

3. Try the Zip Lines at Boundless Adventures

Boundless Adventures is the place to choose if sitting through another dinner sounds boring. The park fills a wooded part of the Purchase College campus with 16 courses and 28 zip lines. A general admission pass gives you three hours in the trees.

Nervous first-timers can start on a low zip line that sits only 10 feet off the ground. The park also runs night climbing on selected dates, and its hours change by season.

4. Go to Playland on a Summer Night

Playland in Rye has run since 1928, which makes it a nostalgic summer date. The park opens from late May into mid-September.

Friday is the night to go, because fireworks run through Labor Day weekend. A daily wristband gets you on the Dragon Coaster and the Grand Carousel. The Pier Restaurant sits on the waterfront inside the park.

5. Walk Through Untermyer Gardens

On a slower day, one of the simplest romantic things to do in Westchester is a walk through Untermyer Gardens in Yonkers. Admission is free, and the gardens hold an Indo-Persian Walled Garden and the Temple of Love. In December and January, the Grand Holiday Illumination runs from 4:30 to 8 p.m.

6. Have a Beer and Play Trivia in Elmsford

The casual option is Captain Lawrence Brewing Company in Elmsford, with a large beer hall and an outdoor beer garden. You can walk in, since it takes reservations only for groups of 20 or more.

Wednesdays add trivia at 7 p.m., and the kitchen closes one hour ahead of the beer hall, so order food early.

7. Head Indoors for an Escape Room, a Paint Night or a Cooking Class

Bad weather does not have to cancel the date. All three of these happen indoors, and they give you something to do together instead of sitting across a table.

The Puzzle Parlour in White Plains has four themed rooms, and each game takes about an hour. At Muse Paintbar in Ridge Hill, an instructor leads guided painting sessions with drinks and bites.

To eat what you make, try Zwilling Cooking Studio in Pleasantville, which teaches hands-on cooking classes.

8. Make It a Late Night at Empire City Casino

Empire City Casino in Yonkers opens every day from 10 a.m. to 6 a.m., so you can arrive long after dinner. The floor has slots and electronic table games such as roulette and baccarat.

You do not have to gamble to enjoy the place. Alley 810 pairs craft cocktails with retro bowling lanes, and DJs play on Fridays and Saturdays. Nonno’s Trattoria serves classic Italian food, and Yonkers Raceway shares the property and runs harness racing all year.

What Couples Usually Misjudge

A few small rules can change your evening if you only learn them on arrival.

• Monday and Tuesday are slow: Captain Lawrence and Blue Hill close on both days, and Playland does the same in summer.
• Blue Hill reservations are final: You cannot cancel once you book, so pick the date with care.
• Playland bans outside food: Leave the picnic at home, because the rule covers drinks too.
• The day you land is shorter than it looks: The drive from JFK to Westchester takes 30 to 70 minutes in light traffic, so book a later table that evening.

Deciding What to Do in Westchester as a Couple

The right answer to what to do in Westchester depends on the kind of evening you both want. Some nights suit a long dinner, and others suit live music or a zip line.

You do not need to fit everything into one outing. Westchester County is large, so one main stop in one area means less time in the car and more time together.

Choose the one that sounds best this week, and save the rest for your next date.