8 Romantic Things to Do in Rye NY and Port Chester in Westchester County

WHY GO: Since it opened at the tail end of the “Roaring 20’s, in 1928, thrilling to the rides at Rye Playland has been one of the best things to do in Rye NY, especially for young couples and families. On the National Register of Historic Places, and, after a recent $150 Million in improvements, it’s still going strong.

Nearby Port Chester, however, has always been the poorer industrial cousin to neighboring Rye and White Plains NY.

So why do the Mavens also recommend it?  Well, one of them, yours truly, spent her formative years working in her father’s downtown Port Chester office, and has watched the town’s revival and growing culinary scene with appreciative interest.

Old Lifesavers Factory Port Chester NY
Old Lifesavers Factory Port Chester NY

Back in the day, the air was fragrant with the aroma of fruit and mint pumped into the air by the Life Saver Factory, based in Port Chester and gone to condo by the mid-80’s.

As a teen, I’d walk to see the Grateful Dead, Jefferson Airplane, Al Stewart, and other rock and roll giants perform at the venerable Capitol Theater. Known as “the Cap,” it closed in the mid ‘70’s, and reopened in late 2012.

Dragon Coaster at Rye Playland Rye NY

But, unless a kid is going to school at SUNY Purchase (now called Purchase College) – in a section of Harrison NY adjacent to Rye – most visitors don’t know about the SUNY Performing Arts Center, and on campus Neuberger Art Museum, or two stupendous nature preserves – both on the shoreline migratory flyway.

The Capitol Theater Port Chester NY

So, come to Port Chester-Rye for spectacular entertainment, Mother Nature, and the cool food scene. There has always been a strong Italian and Latin influence in Port Chester. You’ll find the most delectable dishes in unlikely holes-in-the-walls. Guess who’ll let you in on her favorites?

Ride an historic roller coaster, eat cheap, walk on the serene side, stay in a brand new boutique hotel (that made it onto our 20 Best Romantic Hotels Northeast USA 2021 list), and celebrate with music like it’s 1999, all on this unique Getaway.

More ideas for a dreamy weekend or quick trip throughout New York State, check out our Best Romantic Getaways in NY.

Port Chester NY borders Greenwich CT – so you can dip your toes into New England for a few minutes or days. Find plenty of low-cost attractions off season.

Things To Do In Rye NY

Rye Playland National Historical Register plaque Rye NY

VISIT: Rye Playland, Rye

This iconic, art deco, seaside Rye Playland Park opened in 1928 – just one  year before the stock market crash that set off the Great Depression.  That it’s still going strong is a testament to the appeal of amusement parks in tough economic times.

Rye Playland Pool Westchester County NY

Owned by Westchester County, and managed by the investment firm, Standard Amusements, Rye Playland was recently infused with $150 million in improvements- adding some rides, refacing midway art-deco facades, and completely renovating the Long Island Sound-set community pool.

Midway and ferris wheel at Rye Playland NY

Many of the rides are relatively new – including the 1990 Gondola Wheel, the Double Shot, and new for 2024, Jack the Puppeteer.

The Whip ride at Rye Playland since 1928

However, seven original 1930’s rides remain, which is why this place is on the National Historic Register. The Whip, has been whipping parents and kids around since Rye Playland opened in 2028. One – the 25mph, centrifugally forceful “Derby Racer” – is among the three high-speed carousels left in the United States.

Dragon Coaster entrance Rye Playland NY

The 3,400 ft long wooden Dragon Coaster has been thrilling riders since it opened in 1929.  Check out this Depression-era home movie on YouTube showing men in hats and suits and women with fur stoles enjoying the plunges and turns.

Rye Playland Boardwalk Beach NY

Fans of the movie Big (starring Tom Hanks) might find Playland familiar. Hanks consulted  “Zoltar the Magnificent” right on the beach boardwalk. Park is open in season – check website for days and hours, and fees (including parking and pool). 

The Dragon Coaster is one of the Getaway Maven’s recommended Best Places to Propose in New York State.

SKATE: Playland Ice Casino

The historically important, Playland Ice Casino is the granddaddy of Ice Skating rinks. Overlooking the Long Island Sound, this skating venue is a throwback to the days of refined family outings. The newly refreshed art deco lobby gives visitors a glimpse of the illustrious ice palace it was when it first opened in 1929. Check website for public skating hours, and fees. 

Edith Read Wildlife Sanctuary beachfront Rye NY
Edith Read Wildlife Sanctuary beachfront abuts Playland Amusement Park in Rye NY

WALK: Edith G. Read Wildlife Sanctuary, Rye

This nature preserve is contiguous with Rye Playland, so if you tire of rides and frenetic crowds, take some time to calm your mind. The 179 acre Edith G. Read Wildlife Sanctuary, on a migratory flyway, features three miles of hiking trails through field and forest, and paths along the Long Island sound and a brackish 84 acre lake. Trails open dawn to dusk, free.

Marshland Conservancy in winter along shoreline Rye NY
Marshland Conservancy in winter along shoreline Rye NY

WALK: Marshlands Conservancy, Rye

Next door to first Chief Justice, John Jay’s, childhood home (now the John Jay Heritage Center), Marshlands Conservancy has been the go-to preserve for naturalists for decades. No huge surprise – it should be one of Rye’s main attractions. Marshland’s 147 acres, composed of forest, meadow, and shoreline, offers one of a handful of salt marshes in New York open to the public (without a fee). 

Marshland Conservancy hiking paths in snow Rye NY
Marshland Conservancy hiking paths in snow Rye NY

Photos fail to fully capture the stark beauty of winter, when beaches and tree boughs are cloaked in snow. A two-mile walk out and back to the waterfront might be bracing – but it’s very popular. You’ll meet families with kids, dog walkers, X-country skiers and people who are ecstatic just to be outside. Trails open dawn to dusk, free.

VISIT: Jay Heritage Center, Rye

Learn all about the first Chief Justice of the United States at his home and gardens in Rye NY – now the Jay Heritage Center. There are mansion and garden tours, lectures, and special events. Consult the website for tour times and programs.

Things to do In Port Chester NY and Nearby Purchase

Neuberger Museum of Art SUNY Purchase NY

VISIT: Neuberger Museum of Art at SUNY Purchase

Opened in 1972, the world-class Neuberger Museum of Art is the 8th largest University Art Museum in the United States. Though its exterior is a hulking brick box, soaring galleries inside are bright and airy. This often overlooked college campus museum focuses on African, modern, and contemporary art. That includes an extensive collection of Alexander Calder sculpture, prints, and paintings.

Capitol Theater, aka "The Cap" - Port Chester, NY

ROCK CONCERT/COMEDY: The Capitol Theatre, Port Chester

Drawing patrons from New York City, and once the preferred venue for The Grateful Dead, Janice Joplin and the greats of rock n roll, the Capitol, nicknamed “The Cap,” became a key site for nesting pigeons and mold after it shut down in the mid 1970’s. Thanks to nostalgia with bucks behind it, the Cap was refreshed and renewed, re-opening with a bang in late 2012. Big names have been lured back, so if you’re planning a stay in town, be sure to get tickets in advance.

SUNY Purchase Performing Arts Center NY

PERFORMING ARTS: Purchase College Performing Arts Center, Purchase

The two last events I attended at Purchase College Performing Arts Center were 1) for a Sound of Music movie sing-a-long, and 2) an appearance by the humorist, David Sedaris. This indicates the range of  programming that this college theater offers.

In addition to movies and lectures, PCPAC hosts concerts, dance performances, and theater. Like Yale U. in New Haven CT, this university, known for its Conservatories in the fine and performing arts, counts many notable actors among its alumni. These include Parker Posey, Melissa Leo, Wesley Snipes, Stanley Tucci, Edie Falco, Josh Hartnett, and more. Check the website for upcoming events.

Best Restaurants In Port Chester NY

Tandoori Taste of India Port Chester NY

EAT: Tandoori Taste of India, Port Chester

Tandori in Port Chester is my go-to Indian Restaurant in the tri-state area. Mom and I split a Tandoori chicken – moist and flavorful, right out of the tandoori oven on a sizzling plate of julienned peppers and onions. My husband gets whatever vegan dish the chef recommends. And we all love the crispy papadam – with addictive onion relish – that comes before the meal. For fans of authentic Indian food – you can’t find better than modest spot on Main St. in Port Chester NY.

Paleteria Fernandez Port Chester NY
Paleteria Fernandez Port Chester NY

SNACK/ICECREAM: Paleteria Fernandez

Paleteria Fernandez – a Mexican frozen fruit and cream-pop shop – has gained more than a toehold in Port Chester. The first time I tried one of the dozen or so flavors of this frozen treat, I was hooked. My favorite? Dolce le Leche.  It is an eyes-roll-back-in-the-head, exceedingly delectable frozen version of the creamiest caramel I’ve ever tasted.

The Kneaded Bread Port Chester NY

EAT/LUNCH: Kneaded Bread

Kneaded Bread, a purveyor of Foccocia, Ciabata, Rye, Crusty French loaves, soups, salads and sandwiches, in the shadow of the original Life Savers Factory, remains THE place for the artisanal bread obsessed.

Marianacci's Restaurant, Antipasto, Port Chester, NY

EAT: Marianacci’s, Port Chester

Marianacci’s was my family’s “fine-dining” go-to way back when. And it’s still where the best Old World Italian cuisine and service has been hiding in plain sight for over 70 years. If you want time-capsule worthy stuffed clams, real hearty Zuppa Di Pesce, and simple antipasti free of modern embellishments, you’ll make your way to this tough-to-find, white tablecloth, fuss-over-you-like-family oldie-but-goodie.

Aqui Es Santa Fe Port Chester NY

EAT: Aqui Es Santa Fe, Port Chester

Aqui Es Sante Fe serves up great Modern Columbian food. Nice owners. This sweet little BYO-wine corner café has many fans. Empanadas, and Arepas, are perfect for sharing. Entrees, like simply prepared grilled chicken, beef and salmon are at a reasonable price point. Right across from the Port Chester train station (a Metro North Stop) and a block from the Capitol Theater, it’s a perfect pre concert meeting place.


Port Chester has some surprisingly good eats. The fine-dining Italian restaurant, Alba, has been a crowd pleaser for years. Saltaire Oyster Bar for drinks and seafood. Incazteca for Mex-Peruvian cuisine.

Where to Stay in Port Chester/Rye/White Plains NY

Entrance to The Opus Westchester Hotel White Plains NY

STAY: The Opus Westchester, Autograph Collection,  White Plains NY

The boutique Opus Westchester replaced the Ritz Carlton in downtown White Plains – the most business-oriented city in affluent Westchester County (15 minutes from Rye-Playland). Although this Marriott Autograph Collection Hotel has taken over, it still offers the surprisingly friendly, exceptional service it did as a Ritz. No big surprise, since many of the staff stayed on.

Reception at The Opus Westchester Hotel

Half way (30 minutes) between Greenwich CT and Manhattan, the Opus Westchester is frequented by corporate executives mid-week. But, like its predecessor, it may become a preferred “Staycation” for locals who want to a) get away from the kids, b) rock one more weekend alone BEFORE having kids, or c) just enjoy a splurge and change of scene.

Opus Westchester Lobby

First Impressions of Opus Westchester NY

The eye-catching, art-filled Lobby is now separated from its dimly lit, more intimate lounge. It still serves as a casual restaurant, where guests ease into plush chairs set around small tables. What you will now longer find, however, is the contemporary glass and stone center-room fireplace.

Dining At The Opus Westchester

Cozy dimly lit Lounge at Opus Westchester NY
The Lounge

With the elimination of the fireplace, the Lounge remains a cozy, casual dining space from morning to night (6:30am – 11PM). You can still request everything from omelets to salads and “specialty cocktails.” My personal favorite is the highly flavorful Crispy Chicken Sandwich, served with a side of as-crispy fries. Accompanied by a nice Malbec, it made for the perfect dinner.

Apparently, the Lounge is popular with the lucky people who live in the building: in two on-site Ritz Residential Condo Towers. A good number came to pick up dinner – or stayed for a drink and a bite – on a stormy Thursday night. How did I know they were residents? The staff welcomed them warmly. By name.

Red Horse By David Burke

No need to walk outside – celebrity chef, David Burke, has installed Red Horse at the Opus.

Sweet welcome amenity with fruit, chocolate, and macarons at the Opus Westchester Hotel

A Romantic Amenity

Should you wish to impress your sweet, pre-order this sweet amenity, with dried and fresh fruit, artisanal chocolates, and macarons, to greet you when you arrive. Someone in the kitchen has a creative, artistic eye.

Guest room at The Opus Westchester White Plans NY
Rooms at the Opus Westchester

After a major room renovation, all 146 rooms, including 38 suites, have been updated to the max. Gone is the dated furniture and appointments (e.g. bed skirts), and in their place, hardwood floors covered with area rugs, contemporary furniture, and a more interesting, varied color palette. Cloudlike white duvets, large flat-screen TV’s, however, remain. As did the bathroom decor.

Spa at The Opus Westchester

Opus Westchester Hotel enclosed rooftop pool

Indoor Pool

This enclosed rooftop pool is larger than most at other hotels. It’s particularly welcome and beautiful on a snowy day.

Fitness Room Opus Westchester
Fitness Center

Large and well equipped with machines, weights, and balls, this fitness center is open 24-7 for early morning or late night workout freaks. Room rates off season weekends start at $229, midweek $379.

Courtyard by Marriott Rye NY

STAY: Courtyard By Marriott, Rye 

Right off of the I-95/I-287 exchange ramp, the Courtyard By Marriott Rye on the boarder of Rye and Port Chester is the ONLY place to stay in Port Chester.  So, it’s a good thing it’s nice. The small inviting lobby is inviting features a small café. Refreshed, clean rooms sport flat-screen TV’s, granite counter bathrooms and free wifi.  And one very state-of-the-art and as yet offbeat amenity: parking lot includes two EV (electric vehicle) Charging Stations. So, by all means, drive your Tesla on over!

Port Chester Rye NY Pin


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

    View all posts

Leave a Comment