2020 Date Night Guide {the best active spots in Westchester County}


Shower? Check. Clothes that aren’t meant for working out? Check. Babysitter? Check. “Where do you want to go?” “I don’t care. Where do you want to go?” Sound familiar? We feel pretty lucky to live in Westchester County, where there are tons of options for awesome date nights. But honestly, sometimes the sheer number of places to go and things to do can be overwhelming. Often, we end up sticking to the same old places. We decided to branch out and compiled a list of the best, coolest, most fun, and unique spots in Westchester County for a date night (or a girls’ night out!). To check out more date night ideas, click here. As always, please support our sponsors! Enjoy!


Boundless Adventures is a great destination for a unique and fun outdoor date night activity. Looking to see what your new partner has in them? Are you and your significant other athletic-minded people that are looking for something to do other than eat and drink?  Boundless Adventures is hosting evening special events all season long. And of course, you are always welcome to come during the day as well with friends, family, coworkers, etc.

Receive 10% off with the code date-zip valid for visits through Memorial Day weekend.

Back Nine {Cortlandt Manor}

They offer state-of-the-art golf simulation, along with casual dining and a beautiful sports bar. If that’s not enough, they have live music at least once or twice a month and drink specials during all major sporting events!

Bowlmor {White Plains}

Located less than a mile off I-287, Bowlmor White Plains lets you dine, party, and play in a most unusual and exceptional way — with 56 lanes of bowling, three unique bar and lounge areas, and an expanded arcade featuring 50 interactive games.

The Cliffs at Valhalla {Valhalla}

The Cliffs at Valhalla boasts a variety of terrains – from slab to steep – and a route spread from 5.5 to 5.13 and boulder problems from V0 to V12. Regardless of your interests and abilities, they’ve got something to keep you moving.

Dave & Buster’s {Pelham Manor}

At Dave & Buster’s, their mission is to deliver an unparalleled guest experience through the best combination of food, drinks, and games in an ideal environment for celebrating all-out fun.

The Grit Ninja {Pleasantville}

 Have fun scaling the walls and tackling the obstacle course with your partner at this ninja warrior gym in Pleasantville.

Hudson River Expeditions {Peekskill}

Hudson River Expeditions provides kayak, canoe, and paddle board rentals, tours, and instruction for the novice to the experienced paddler in Cold Spring and just outside of Peekskill.

iFLY Indoor Skydiving {Yonkers}

Experience the thrill of skydiving without jumping out of an airplane! Your two-hour experience includes hands-on training with a professional coach, flight gear rental, and two or more flight rotations.

The Pottery Factory  {Mount Kisco}

Create paint-your-own pottery, candles and glass fusing, or an instructor-led Paint & Sip class and more. You’ll always have fun for hours creating with them.  

Pruyn Sanctuary {Chappaqua}

Located in the Town of New Castle on Route 133-Millwood Road, Pruyn Sanctuary protects 92-acres of open space and offers over two miles of hiking trails through diverse habitats, including a system of boardwalks through Gedney Swamp. One of the most popular sanctuary features is a small butterfly and hummingbird garden open to the public.

The Puzzle Parlor {White Plains} 

The Puzzle Parlour is a live-action adventure that is unlike anything you have ever expereinced. Come with your friends, family, colleagues or team to tackle the challenges together. You’ll have a total of 60 minutes to UNPLUG from the digital world, INTERACT with your team of adventurers, and ESCAPE from your busy life. The question is, can you escape the room?

Rye Playland {Rye}

Playland’s 280 acres are intended to be the jewel in the crown of Westchester’s extensive park system. Enjoy picnic areas, restaurants, three ice-skating rinks, swimming pool, two beaches totaling approximately 7,900 feet of shoreline, in addition to the thrilling amusement rides.

Sleepy Hollow Cemetery Walking Tours {Sleepy Hollow}

Whether you are a history buff, love sculpture, interesting cemetery symbolism, or just want to enjoy the pretty scenery, a visit to historic Sleepy Hollow Cemetery’s 90-acre grounds is a treat. Make the most of your time there by taking one of their guided tours to unlock some of the secrets behind the stones!

Sound Bound Fishing Charters {New Rochelle}

Welcome aboard Sound Bound Fishing Fleet, your ticket to the most exciting fishing the Northeast has to offer! Consisting of 3 vessels and 3 locations, the Sound Bound Fleet is always positioned to give customers exactly what they are looking for, the fish of a lifetime!

Where will you be going on your next date night?

 Be sure to read all the posts in our Date Night Guide series by clicking here.