All right, if we’re being honest, it’s highly unlikely that you or anyone you know has done all of the things on this list, and we’d never shame anyone as being a “Fake Westchesterite” for skipping out on any of them. That said, whether you’re new to the area or have lived here all your life and are just looking for a fun way to spend an afternoon, see how many of the below activities you’ve yet to check off your list!
Food & Drink
1. A Walter’s Hot Dog
Start strong: Mamaroneck’s oddly pagoda-shaped landmark has been slinging grilled, split dogs for almost a century, and one only needs to try one to understand why. While everyone has their favorite (pretzel buns, smashed potato puffs on top, etc.), your best bet is to start with the classic: a single beef-pork-veal blended dog slathered in Walter’s Mustard.
Chef Peter Kelly’s waterfront restaurant in Yonkers has a view that’s to die for, and a menu to match. The Iron Chef champion is always tweaking the seasonal offerings and planning special holiday dining events for his flagship restaurant, and is frequently involved in local festivities like Hudson Valley Restaurant Week, the annual Yonkers Film Festival, and even our own Wine & Food Fest, so there are always plenty of great opportunities to drop in to try a new dish.
The food alone would be reason enough to make a reservation, but Blue Hill Farm’s efforts in creating ethical and sustainable farming practices are what really turn a meal here into an experience. The ever-rotating menu created by James Beard Award-winning chef Dan Barber is a bit pricey, but as a splurge it’s undeniably worth it. (A few years back it was named one of the 50 best restaurants in the world.) You can even try the Café and Grain Bar and get a smaller taste of what Blue Hill has to offer.
Locals will swear by this 24-hour North county deli with the same fervor as your college roommate from California describing the importance of ordering “Animal Style.” For more that 50 years Rocky’s has served as the meeting place for hungry locals, goofy teens, and anyone in need of a good hangover baconeggandcheesesaltpepperketchup on a roll. (Yes, that’s all one word.) The food is exactly what you need no matter when you need it, but even the assortment of basic provisions and specialty junk food is perfectly curated to provide a New Yorker their childhood comforts when needed most.
5. Take a Booze Cruise Down the Metro North
Speaking of hangovers … did you know drinking is permissible on Metro-North trains? Yes, save for a few holidays (we’re looking at you, New Year’s Eve and St. Pat’s), as long as you aren’t getting out of control or drinking on the platform, it’s perfectly allowable to knock back a cold one on your way to an evening out in The City.
6. Ice Cream at The Blue Pig
Homemade ice cream from locally-sourced, steroid- and antibiotic-free dairy and fresh local produce, this is ice cream as it was meant to be. Lisa Moir, who bought The Blue Pig in 2010, is also heavily into environmental sustainability, as evidenced by the shop eschewing plastic straws for their throwback (and more environmentally friendly) paper counterparts.
7. Apple Picking & Apple Cider Donuts
If there’s one quintessential fall activity in the Hudson Valley, we can all agree it’s going apple picking, if only for the chance to score some fresh cider and just-out-of-the-oven apple cider donuts. What we can’t agree on is what town has the best donuts round. We suggest starting here and working your way down the list.
8. Dine al Fresco on a Rooftop Bar
Definitely en vogue right now, open-air dining is something Westchester has really gotten behind. With gorgeous cityscapes and breathtaking sunsets over the Hudson in the West and the sound along our Eastern shores, grabbing a drink and some light fare in the more temperate months can’t attain a more perfect quality than when enjoyed touching the sky.
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9. Enjoy the Ultimate Burger(s)
When it comes to certain foods in Westchester, competition is friendly, yet fierce. Pizza, bagels, ice cream, the aforementioned cider donuts…. Everyone has a favorite, but we’ve never understood limiting yourself to just one. Even if you’re a die-hard Oath or Piper’s Kilt fan, pretty much every major town and burb has its own signature burger. Then again, if you’re really more the ‘Go big or go home’ type…
10. Attend Westchester Magazine’s annual Wine & Food Fest
This is kind of tooting our own horn, but if you’re a foodie you’d be crazy to miss out, so toot toot. Featuring dinners hosted by celebrated local chefs, wine tastings, kids events, a Grand Tasting Village with nearly fifty local restaurants and food trucks and over two hundred wines, and oh yes, our Burger & Beer Blast which every year crowns the absolute best burger in all of Westchester.
11. Hit Up The Westchester (duh)
It may sound a little on-the-nose, but come on; there’s a reason this mall gets a capital ‘The.’ Full of middle and high-end shops, delicious food, and plenty of pampering and entertainment options, The Westchester is the tops when it comes to local shopping. Even if you can hit up a good chunk of the stores in your local mall, the one-stop-shop benefits and sheer spectacle of it all make this a mall experience you have to try at least once.
12. Get Crafty at the Lyndhurst
â€‹The country’s biggest crafts fair takes place at the Lyndhurst Castle twice a year in Tarrytown. With people coming from all over the nation just to attend, why aren’t you hopping a quick car ride to scope it out? Showcasing over 275 markers, artists, designers, and craftspeople at last count, there’s pretty much guaranteed to be something for everybody.
13. Stew Leonard’s
Pet a cow, eat a donut: it’s a win-win. This regional classic is like your typical grocery store on steroids — which is ironic considering their selection of organic and all-natural products. Samples are plentiful, in-house products are always fresh and scrumptious, and if you stop by during the late spring/early summer you can even enjoy the arrival of adorable baby animals like sheep, goats, and calves. (Note: If you find animatronics creepy, you’re allowed to skip going inside, but the food is really good so you may want to soldier through.)
Arts & Entertainment
14. Take in a Q&A Screening at Jacob Burns or The Picture House
Summer blockbusters are great, but if you’re in the mood for something a bit artsier or and indie flick, heading down to your local art house is your best bet. For something truly special, check in with The Picture House in Pelham or the Jacob Burns Film Center in Pleasantville. Not only do they feature some truly interesting foreign and domestic films, but your can snag tickets to special advance screenings and hosted Q&A sessions with the directors and actors. Play your cards right, and you can even bump into some celebrities. (Ensuing wacky, mad-cap romantic entanglements not guaranteed.)
15. Art Galleries Everywhere
Why head into the city to check out the MoMA for the umpteenth time when your home county is full of celebrated, innovative, and up-and-coming museums and galleries in New York? Not only do we have the Hudson Valley Center for Contemporary Art, but we’ve also got the Katonah Museum of Art, the Neuberger, pretty much half of downtown Peekskill, and for that matter art walks and gallery showings in pretty much every major city and town up and down the Hudson River. Heck, we had the Hudson River school of art. You couldn’t throw a rock without hitting amazing art in Westchester (and you really shouldn’t because odds are you couldn’t afford to pay for it).
16. Purchase some Culture
Purchase College’s Performing Arts Center puts on 80 different performances each year across four theaters, ranging from dance and theater to music and even family-friendly events. No matter where your interests lie, you’re sure to find something that piques your interests.
17. Explore Space at an Indoor Planetarium
Space. The final frontier. Well unfortunately, as Elton John sang, it’s also cold as hell. If you love going stargazing but hate donning three jackets and packing a thermos of cocoa just to get a few hours of telescope time in New York, you really should be checking out the indoor planetarium at The Hudson River Museum. Not only can you scope out the night sky above Yonkers, but also above Mars and anywhere else the evening’s program takes you!
18. Become a Master Builder
LEGOLAND Discovery Center Yonkers is a whole-family delight. Build, play, snack, learn some Spinjitzu, watch a 4D movie, and just generally have a blast surrounded by everything LEGO: Try out for each year’s Creative Crew, brush up at the Master Builder Academy, or just enjoy some cool rides. Adults-only nights are even available on a bi-monthly for bigger brick fans!
19. Bet a Pony, Play a Slot
For more than a century, Empire City Casino and Yonkers Raceway have been Westchester’s go-to spot for high-rollers looking to relax and everyday folk looking to score big. With recent changes in legislation and plans for expansion, Yonkers is quickly supplanting Atlantic City as the go-to gaming and entertainment destination for many Westchester residents.
20. Hard Rocking at The Capitol Theatre
Don your favorite band tee and leather for a rock show show at any of our county’s legendary venues. The Capitol Theatre in Port Chester and Peekskill’s Paramount Center are two of the biggest, and they’re surrounded with more food and drink than you can shake a stick at. Come early, stay late.
21. Complain About Our Local Taxes
Call it humblebragging, but Westchester really is one of the most highly taxed regions in the country, and kvetching about it is practically our official sport. We’re quick to quote you our insane rent prices, the shrinking middle class, and our very specific opposition to new tax changes. But as seriously as we take these issues, we also seem to take a perverse pride in them, sort of how you’re allowed to make fun of your own family but nobody else is.
22. Complain About Being Called “Upstate”
Professing how much we hate being called “upstate” even though no one ever really seems to call us that unless they live in Manhattan (and even then it never really actually bothers us that much). If complaining about taxes is our national sport, “It’s NOT Upstate!” is probably our county motto.
Their summer music festival alone is worth putting on this list. Grab a blanket, pack your picnic, and enjoy some incredible outdoor music on the lush estate grounds. Wander the gardens, tour the mansion, and enjoy a concert, all on the same trip!
24. Take In an Outdoor Movie at Kensico Dam
Aside from housing a beautiful park, Kensico Dam Plaza is a happening event space. (Our own Wine & Food Fest hosts several events there.) It also transforms into a dynamite movie theater every summer, as an enormous screen and speakers go up, food trucks drive in, and families and friends gather ‘round to enjoy cinematic goodness in the cool night air. Not close enough? There are plenty of other outdoor movie venues throughout the county every summer!
Or the New Croton Dam. Or FDR State Park. Or Anthony’s Nose. Or Bronx River Parkway Reserve. Or the dozen other amazing parks and trails we have here in Westchester, with or without your canine friends.
26. Get Your Horseman On at the Great Jack O’Lantern Blaze
For more than a dozen years the Great Jack O’Lantern Blaze in Croton has drawn large crowds and even larger celebrity attendees. (Hiyah, Neil Patrick!) Thousands of real and imitation pumpkins go into crafting amazing, towering sculptures every year, and they just keep getting bigger and better. It even has its own soundtrack!
27. Spend the Day at Rye Playland
We’re not ones for gatekeeping, but you might genuinely not be a Westchesterite if you’ve never ridden the Dragon Coaster. For nearly a century Playland has been the summertime Mecca for Westchesterites the way Adventureland is for Long Islanders. Among the beach and boardwalk and carnival games sits the Dragon Coaster, one of the oldest wooden roller coasters in the Northeast. Before you grab cotton candy and shoot water in a clown’s mouth, keep up tradition and take a ride on the dragon.
28. Untermeyer Gardens
Untermeyer Park in Yonkers is full of history. Scenic views, Roman style gardens, free summer concert series, and for the spooky guest: a macabre tie to the Son of Sam killer. Personally, we recommend the concerts. Even if your showtime isn’t until 7:30 p.m., regulars know to show up as early as 4 to grab a good seat and picnic until show time.
Speaking of music, this mini-Woodstock festival has been going on for over 50 years, founded in part by the legendary Pete Seeger. Upwards of 15,000 guests come out annually to hack the sack, feel the groove, and just get really far out, man. It’s also America’s oldest and largest music and environmental summer festival, so your out-of-town friends should definitely appreciate your in-the-know invite.
If you’re a little more new-school in your musical tastes, you’ll love P-Fest. Nine hours of music from nearly 20 bands spread across three separate stages, the concert combines local artists with big-name acts like Robert Randolph and the Psychedelic Furs. Tickets are reasonably priced, and you can even camp out in Tent City for some added fun.
Have you ever wanted to take a nice walk along the river, see some scenery and art, but also take a day trip to a neighboring village all in the same day? Well, the RiverWalk Initiative had the same thought. 33.4 miles of the eventual 51.5 mile path have been completed by constituent municipalities, including sections in Yonkers, Dobbs Ferry, Irvington, Sleepy Hollow, Ossining, Croton, and Peekeskill. Lined with parks and picnic spots, the hope is that other counties will donate portions of their shoreline, allowing Westchester residents to hike or stroll not just from town to town, but even farther into the Hudson Valley!
All right, if we had to pick an official real sport for Westchester, we’d have to give a tiny, respectful round of applause to golf. With some of the best courses, clubs, and players in the Northeast that’d be enough to make this list, but with the game’s growing popularity among locals of every gender and age group, it’s also shedding its formerly stuffy public image. In Westchester, golf is for everyone.
33. Spend the Holidays at Lyndhurst
â€‹Once railroad tycoon Jay Gould’s summer home, historic Lyndhurst Castle (yes, he summered in a castle) in Tarrytown is a testament to the height of opulence. Don’t think you’re just getting tours of some stuffy old house, though. Local theatre is regularly performed throughout the home, a perfect setting for renditions of Dickens and the like. Stop by during the holidays and you’ll find not only period-appropriate (and gorgeous) decorations, but scenes in which each room has been transformed into a different classic fairy tale. Kids love it, almost as much as the adults!
34. Pretty Much All of Sleepy Hollow
Come on, you didn’t really think we’d forget about Sleepy Hollow, did you? Even the town decided to ditch the “North Tarrytown” moniker in favor of its more famous identity. Check out the Old Dutch Church, covered bridges, and Sleepy Hollow Cemetery with original 17th Century gravestones. Visit in fall for haunted hayrides, haunted houses, historic tours, and all manners of spooky fun. Is it a little touristy to do all that? Well, sure. But it’s Sleepy Hollow. Go ahead. Be silly and enjoy the kitsch!
Think we left something off our list? Add your submission below!