22 Must-Do Activities to Make This Your Best Westchester Summer Yet

Our guide to getting the most fun out of the county over the next few months.


Published:

By Paul Adler, Nick Brandi, Samantha Garbarini, Sarah Longstreth, and Amy R. Partridge; Edited by Amy R. Partridge; Featuring photography by Ken Gabrielsen & make-up and hair by Ashley Lauren Beauty Lounge


1. Make the annual Pilgrimage to Rye Playland

It’s not summer in Westchester if you don’t at least spend one day — or night — at the famed amusement park in Rye. Best known for the Dragon Coaster, Playland also offers thrill rides like Super Flight, Double Shot, Derby Chaser (left) and Thunder Bolt; tamer, family-friendly options include bumper cars and a zombie castle, plus water rides (Playland Plunge, Log Flume), and Kiddyland, perfect for the preschool set. Nighttime fireworks and popular concerts round out the fun. (Note: the Grand Carousel will be closed this summer.)

 

2. Chow down at a new waterfront restaurant

With the Sound on one side and the Hudson on the other, Westchester is prime for waterfront dining, and new spots are taking full advantage. At Factoria in Peekskill, Fin & Brew serves fresh seafood from its second-floor perch overlooking the Hudson, while quality microbrews spill out onto the lower patio from River Outpost Brewing Co. Sunset is the best time to hit the expansive, date-worthy terrace at 3 Westerly in Ossining (shown above). Farther south, grab a lobster roll on the patio at Hudson Farmer & the Fish in Sleepy Hollow or a craft beer and MLB game on TV at the casual Barley on Hudson. On the other side of the county, Port Chester’s Colony Grill (slated to open by press time) does bar-style hot-oil pies fronting the Byram River.

 

3. Catch a movie under the stars

Take in a blockbuster at one of the county’s summertime outdoor film series. Enjoy classics and concessions at John Jay Homestead in Katonah for $10 per car, or catch free screenings near you at, among other places, Senasqua Park in Croton, Ridge Hill in Yonkers, Neighborhood Nights in parks around White Plains, and at the annual Entergy Screenings Under the Stars at the Kensico Dam in Valhalla (shown above).

 

4. Hunt for treasures at Hastings flea

Support local artisans and seek out something special on the second Sunday of each month as the train-accessible riverside market opens up for a day of live music, food, crafts, and community. Find unique vintage fashions and handcrafted masterpieces, sample street snacks from food trucks, enjoy live music and face-painting, and make a day out of exploring the walkable Rivertown area.

 

5. Get some sand between your toes

It ain’t the French Riviera (or even the Jersey Shore), but Westchester’s waterfront areas do offer the promise of a viable beach day — without the trek or the traffic. On the Sound Shore, options include New Rochelle’s Glen Island Park, Rye Town Park & Beach, and Playland Beach (shown above), all of which offer Long Island Sound access. On the Hudson side, Croton Point Park Beach is popular for its scenic views and spacious beach, perfect for soaking up the sun.

 

6. Indulge in ice cream

A standard scoop isn’t the way we’re doing ice cream in 2018. (Dare we say that’s too vanilla?) Instead, bring on the crazy milkshakes — topped with a slice of cake at Armonk’s SugarHi, drenched in syrup and whipped cream at Stone Fire in Mount Kisco, or chock-full of cookies at Mt. Kisco Diner. Grab a cone of Bona Bona ice cream with torched-marshmallow topping at Madison Kitchen in Larchmont, or sandwich some scoops into a doughnut at Longford’s in Rye. Got a few friends? Head to The Parlor in Dobbs Ferry for the Pizza Ice Cream Sandwich, a round of pizza dough filled with ice cream, Nutella sauce, and caramel-bacon-popcorn crunch.

 

7. Master a ropes course

Being told to “Go climb a tree” is really good advice if one is talking about Boundless Adventures, on the campus of Purchase College. Test your boundaries at this new eco-friendly aerial adventure facility, which offers nine obstacle courses with zip lines, bridges, and rope challenges, in an eight-acre hardwood forest park. Open 7 days a week after June 11, with three-hour sessions costing $59 for ages 12+. (See #11 for another place to hit the ropes.)

 


Photo by Econosmith

8. Soak up a summer festival

As the weather heats up, so does the county’s impressive roster of summer fests. For those craving an all-out music extravaganza, look no further than Clearwater’s Great Hudson River Revival. This Croton-on-Hudson favorite features big-name performers like The Mavericks, They Might Be Giants, and Ani DiFranco. The Pleasantville Music Festival is yet another beloved local bash, with thousands attending the food-and-beer-filled event featuring a battle of the bands and music that ranges from R&B to rock. For a more artsy outing, try the White Plains Jazz Fest, which features more than a dozen jazz greats on stages throughout the city.

 


Photo by Ira Block

9. Hit a rooftop for drinks

Going out tonight? There’s a rooftop for whatever mood you’re in. At Tarry Lodge in Port Chester, the chic terrazzo, with its flower-lined pergola, is perfect for a relaxed after-work drink. In Irvington, the riverfront rooftop at Red Hat on the River draws more of a see-and-be-seen crowd sipping ice-cold cocktails and glasses of rosé. Winston in Mount Kisco (shown above) is the place to be on Wednesday nights, when patrons pack the roof to hear live music. In White Plains, Freebird will debut its roof deck this summer, an escape from the city’s hustle and bustle, serving grilled dishes and beers on tap.

 

10. Experience the Westchester Children's Museum

Spend a day exploring at this new-ish museum in Rye (right next to Playland). Established just two years ago, the museum provides an interactive, educational play place for every age group, from infants and toddlers to tweens. Hands-on exhibits and a wealth of weekly programs let kids unleash the artist, scientist, or roller-coaster engineer within.

 


Photo by Heather Sommer

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11. Check out the newest hotspot, Factoria at Charles Point

It’s not often that a new project of this scale opens in Westchester, so you must go to Peekskill this summer to experience Factoria, the hybrid event space/entertainment complex/food-and-drink destination on 11 acres at the edge of the Hudson River. What’s there? For starters, Spins Hudson, a 40,000 sq. ft. adventure venue, complete with indoor and outdoor aerial ropes courses, a two-story laser tag arena, arcade games, and bocce and shuffleboard courts. The complex is also home to River Outpost Brewery, which brews IPAs, pilsners, and stouts on-site under head brewer and Captain Lawrence alum Justin Sturges. Upstairs is the industrial/nautical chic Fin & Brew restaurant (shown above + see #2 for more information) — and what we’re betting will be the hottest patio scene of the summer. (The event space at Factoria is reserved for weddings and private parties.)

 

12. Do Good While Eating Well

Despite all the ingredient details listed on menus, farm-to-table dining is often removed from the farm. Not so at Purdy’s Farmer & the Fish in North Salem, which will host a monthly series of intimate dinners this summer amid its four acres of terraced farmland. (Yes, the summer sunsets are as spectacular as you’d expect.) The price tag is $300 for five can’t-get-any-more-local courses with wine pairings and a front-row seat to the action as chefs cook over open fire. Proceeds benefit good causes, including Feeding Westchester, and scholarships for local students to study agriculture, among other things. (Call 914.617.8380 for dates and reservations.)

 

13. Work out in the great outdoors

Plenty of Westchester gyms and recreational areas sport some prime ways to get in shape under the great blue sky this summer. Mamaroneck’s Push Fitness runs Push Max Outdoor Boot Camp, which brings members to Mamaroneck Harbor during the warm months, where they can do high-intensity training waterside. SUP Westchester, a water-sports equipment-rental service also in Mamaroneck, features a one-hour group class for participants ages 15 and up, as well as a 1.5-hour group SUP Yoga class — both of which have participants working out atop a paddleboard. For those who prefer free-of-charge outdoor recreation, Westchester also boasts plenty of biking and hiking trails, ranging from the 51-mile Westchester River Walk to the incredibly scenic Ward Pound Ridge Reservation.

 

14. Spray yourself tan

We can’t in good conscience condone the natural way of getting a tan, but we still want that healthy summer glow. That’s why we’re loving all the spray-tan options now available in Westchester. GLOW in Rye Brook has the distinction of being the only county location doing organic custom airbrush tanning, while Platinum Tanning in Hartsdale and all three Solar Escape Tanning locations (Eastchester, White Plains, and Port Chester) offer the high-tech UV-Free Norvell Auto Revolution Sunless Spray Tan machines. Or, for the ultimate in convenience, have the tan come to you with mobile spray-tanning bar Tantrum Spray Tan. Book an appointment and Verplanck-based owner Joy A. Snyder brings her 100% vegan, paraben-, gluten-, and nut-allergen-free tanning products right to your home.

 


Photo courtesy of NYC Water Skiing and Wakeboarding School

15. Boost your water-sports skills

They may call it NYC Water Skiing & Wakeboarding School, but it’s got launch sites right here at Peekskill’s Charles Point Marina and Lake Mahopac. Just $175/hr Mon-Thurs and $195/hr on weekends gets you and your crew some high-quality time on planks, boards, and tubes. Adults and kids 5+ are more than welcome, and no prior experience is necessary — their experienced boat captains will happily show you the ropes.

 


Photo by Peter T. Michaelis

16. Take flight

You can fly the friendly skies of Westchester like a golden sun god at any of several local venues. Channel your inner Jules Verne for $300 per person at Bedford’s Balloons Over Westchester (shown above), or show that you have the right stuff with fixed-wing flying lessons from Performance Flight in West Harrison, whose Experience Flight package runs $399. Would-be rotor-heads can take a thrill ride with Wings Air at Westchester County Airport, where helicopter-flying lessons include a 30-min ride for $395, or an hour for $750. Otherwise, you can surf the air currents while never stepping outside at Yonkers’ iFly in Ridge Hill, where two flights are just $89.95.

 


Photo by Brian Haeffele

17. View some art al fresco

Art lovers, take note: Our area boasts a veritable gallery of artistic attractions over the summer. One of the county’s biggest creative events, The White Plains Outdoor Arts Festival, has been featuring local painters, photographers, glassworkers, jewelers, and other area artisans in Tibbits Park in June for 55 years. For those with a soft spot for sculpture, The Donald M. Kendall Sculpture Garden (aka the Pepsi Sculpture Garden) in Purchase and Nyack’s Edward Hopper House Sculpture Garden are both prime spots to see incredible works out in the open air. Or, give the gardens outside Kykuit in Sleepy Hollow a look (shown above). The opulent Rockefeller estate boasts more than 70 world-class works.

 


Photo by Toby McAfee

18. Bring kids to the Summer Fest

Find a lineup of family-friendly fun all summer long at the Cross County Shopping Center’s 8th annual Summer Fest. Enjoy music and food-truck treats on Foodie Fridays; rock out at a series of live concerts; take full advantage of free yoga and fitness classes in June; take the kids to story time with local celebrities; and marvel at fireworks displays in July.

 


Photo by Stafan Radtke

19. See if you can make a great escape

Westchester boasts at least four escape rooms where you can test your mettle when the heat is on. The Center @ 862 in Scarsdale offers the Gamer’s Challenge Room, while New Rochelle’s Hour to Exit lets you practice your detective skills or race the clock to close Pandora’s Box. The Puzzle Parlour in White Plains dons a Victorian motif for things like their Vampire Room, while Great Escapery brings the adventure to you with their mobile escape room, featuring Zombie Apocalypse.

 


Photo by Twah Dougherty

20. Spend a day at the farm

Turn a lazy summer Saturday or Sunday into a day full of farm-centric activity at Stone Barns Center for Food & Agriculture in Pocantico Hills (shown above). At the renowned farm — known for its devotion to creating a sustainable food system — you can bulk up on agricultural knowledge through various educational activities and guided tours, or just walk the gorgeous grounds, explore the greenhouse, and grab locally sourced snacks and goodies at the Blue Hill Café & Grain Bar. For a kid-friendly farm experience, head to Katonah’s Muscoot Farm. At the 700-plus-acre county park, kids get a glimpse of what farm life was like in the past and can spot pigs, horses, chickens, and other barnyard animals. Plus, admission is free, and every summer Sunday, Muscoot hosts a farmers’ market chock-full of local fare. In August, be sure to head to Wilkens Fruit & Fir Farm in Yorktown Heights for pick-your-own peaches and nectarines (call first to confirm harvest times), plus wine tastings at the farm’s White Hill Vineyard tasting room, and farm-fresh produce and treats at the bakery/country store.

 


Photo by M. Hara

21. Soothe your soul at a summer concert

Crowded stadiums aren’t the only way to catch some tunes this season. Westchester is home to more calming summer concerts than you can shake a conductor’s baton at. The Hammond Museum and Japanese Stroll Garden in North Salem annually holds its Moon Viewing Concert (shown above), featuring incredible paper lanterns and traditional Japanese Music. Meanwhile, Katonah’s Caramoor Center for Music and Arts holds two premier events: Its American Roots Festival and Jazz Festival are relaxed affairs with lineups of celebrated artists performing on the center’s scenic grounds. The Peekskill Riverfront Summer Concert Series also offers a musical respite, with an impressive view to match, on Wednesdays throughout the summer.

 

22. Go to a Latin food crawl in Port Chester

Start your tour of this town’s incredibly diverse dining scene with a sweet stop at La Flor De Jalisco, a Mexican bakery making sugary churros and moist slices of tres leches cake. Head down Westchester Avenue to Taqueria La Picardia for tender al pastor tacos, and then try the Colombian arepas — and hit the sangria bar — at Aqui Es Santa Fe (shown above). After, pop by Acuario for fresh Peruvian ceviche. On the way back, don’t miss a summer staple: fruity paletas from Paleteria Fernandez.