Things To Do In Rye NY: Top 15 Most Unique Spots | Stanton House Inn

Charming house within walking distance of the Rye Country Store and shopping on Main Street

Welcome to Rye, NY, the smallest of Westchester County’s cities, yet teeming with charm that belies its size. Here, the Long Island Sound gently caresses the shoreline, whispering tales of adventure to anyone who’ll listen.


This seaside town, as picturesque as a postcard, boasts a quaint downtown shopping district that’s as enchanting as a well-spun yarn. High-end fashion boutiques rub shoulders with gift galleries, and a veritable “Restaurant Row” promises culinary delights that would make even the most discerning food critic’s mouth water.


Rye is a haven for all ages, its laid-back charm and family-friendly atmosphere as inviting as a cozy fireside on a winter’s night. The city is steeped in history and culture, its downtown district a patchwork quilt of shopping and dining spots, a wildlife refuge, natural wonders, and breathtaking Long Island Sound waterfront views. Ready to take the plunge into the best this city has to offer?


Ready to dive headfirst into the best things to do in Rye, NY? Let’s get into it:


Quick hits

  • Explore the magical world of Rye, NY with its amusement parks and heritage centers.
  • Sip on delicious treats from Longford’s Ice Cream or savour delicious cuisine in downtown Rye
  • Find a cozy place to stay after an adventurous day exploring nearby towns!


Rye, NY, map, including top attractions like Rye Town Park, Rye Nature Center, and, of course, Rye Playland Park
Map design by Stanton House Inn

A Brief History of Rye, New York

Old postcard of the train station

A 2010 study found that a whopping 75% of the acreage of Rye, NY, or 3,954 acres to be precise, was archaeologically sensitive. These lands whispered tales of Indigenous and First Nations contact sites. Two villages are confirmed to have existed: one on Manursing Island, and the other on Milton Point.


Colonial Era

Now, Rye was once a part of Fairfield County, Connecticut, and was the domain of the Sachem Ponus, of the Ponus Wekuwuhm, Canaan Parish. The name “Peningoe Neck” may ring a bell, as it was probably named for this very chieftain.


Rye was born in 1660, brought into existence by three men from Greenwich, Connecticut, namely Thomas Studwell, Peter Disbrow, and John Coe. John Budd and his family were among the subsequent landowners.


Industrial Era

The 19th and early 20th centuries saw Rye as a sanctuary for the affluent Manhattanites who fled the city’s heat in coaches or boats. Its location on Long Island Sound and its numerous beaches attracted visitors of all means, who sought short stays at cottages and waterfront hotels.


In that era, the towns along the Long Island Sound shoreline vied with each other for the favor of beachgoers from New York City. Each town had its own gimmick to attract the riders of the MetroNorth train line. Old Greenwich, CT, for instance, changed its borough name to “Sound Beach”. Rye, on the other hand, upped the ante with hotels, resorts, and amusement parks.


However, the crowds were not always welcome. The local residents, disgruntled by what was described as “unsavory” behavior, led the government of Westchester County to buy two existing theme parks, Rye Beach and Paradise Park. These were then merged to create a government-owned amusement park.


Today, Rye is still home to the legendary Playland Amusement Park, a local jewel that has been entertaining families for generations.


Modern Era

Rye has been a city since 1942, evolving from a quaint village into a bustling hub with over 15,720 residents in Westchester County, New York. Rye’s rich history is evident in its architectural gems and iconic attractions.


Now that you’ve had a taste of Rye’s rich history, brace yourself for the numerous activities and experiences that are yet to come!


The Best Things to do in Rye NY

Rye is home to significant bird habitat

From thrilling amusement parks to serene nature sanctuaries, Rye, NY, offers a plethora of exciting things to do. This guide will lead you through Rye’s top attractions, such as:

  • Rye Playland Amusement Park
  • Playland Ice Casino
  • Jay Heritage Center
  • Rye Free Reading Room
  • The Rye Arts Center
  • Downtown Rye


Prepare yourself for an adventure you won’t soon forget!


Rye Playland Park

Playland Park, the iconic amusement park full of live entertainment, special events, exciting rides, and childhood memories galore

A visit to Rye wouldn’t be complete without a trip to the iconic Rye Playland Amusement Park, a seasonal wonderland with over 50 delightful rides and attractions, often compared to the famous Coney Island. Feel your heart race as you hop on the classic Dragon Coaster or spin around on the Gondola Wheel, then cool down with delicious treats from the concession stands.


Despite experiencing a fair share of highs and lows since its inception, Rye Playland Amusement Park continues to be a cherished destination for locals and tourists alike. Playland offers a variety of attractions and amenities, including:

  • Cool ice rinks
  • An Olympic-size pool
  • Scrumptious restaurants
  • Awesome concert series


Westchester Children’s Museum

The Westchester Children’s Museum, near Rye Playland Beach, is an ideal spot to engage your inner child and make lasting memories. This interactive facility offers a variety of educational exhibits for children of all ages.


Playland Ice Casino

If you’re looking to cool off after a day of excitement at Playland Park, head over to the Playland Ice Casino, where you can glide gracefully across the ice or learn some new moves at various skating and hockey clinics and camps.


With public skating sessions featuring rad black lights and live DJs, Playland Ice Casino is one of the most entertaining ice skating rinks, offering a fun and frosty destination for kids and adults alike.


Jay Heritage Center

For history buffs, the Jay Heritage Center is a must-visit destination. This not-for-profit organization manages the 23-acre Jay Estate, the childhood home of Founding Father John Jay, located near the Edith G Read Natural Park. Take a stroll through the mansion or stroll the grounds, soaking in the rich history and picturesque surroundings.


The Jay Heritage Center offers a variety of events and programs, including:

  • Nation’s history
  • Social justice
  • Architecture
  • Landscape conservation
  • Environmental stewardship


This is an ideal spot to delve deeper into America’s political history and the intriguing life of John Jay.


Rye Free Reading Room

Rye's public library

For a quiet escape, visit the Rye Free Reading Room, the town’s public library. With a wide selection of materials, programs, and spaces, this historic library is a sanctuary for bibliophiles and knowledge-seekers alike. The Rye Free Reading Room is one of the area’s oldest national historic landmarks, dating back to 1884.


This peaceful retreat offers an opportunity to delve into the world of literature at your leisure.


The Rye Arts Center

The Rye Arts Center

Let your creative spirit soar at The Rye Arts Center, a hub for artistic expression and exploration. The center offers a variety of programs and activities designed to spark creativity and innovation, including:


  • Visual arts
  • Performing arts
  • Music
  • STEAM (Science, Technology, Engineering, Arts, and Mathematics) education


This is an ideal setting for discovering new talents or refining your existing skills.


Downtown Rye

The center of town is a lively area with plenty of shopping, dining, and other services to enjoy. Some popular shops to explore include:


Take a stroll through the charming streets and discover all that the area has to offer.


Don’t forget to satisfy your taste buds with delectable meals at:


This is a prime spot to shop, dine, and experience the finest offerings of Rye, NY!


Outdoor Things to do in Rye, New York

Enjoy the warm sand beach and the chance to spot marine life at Rye beaches

Rye, NY, is a haven for nature lovers and outdoor enthusiasts. With a wide range of outdoor activities, there’s always an adventure waiting around every corner.


Rye Town Park and Oakland Beach

Rye Town Park and Oakland Beach is a beautiful destination for a day spent outdoors. It offers:

  • Stone walls
  • A stone bridge
  • Terrace overlook
  • Staircases
  • Ramps
  • Pathways
  • Lush lawns
  • Towering trees
  • Vibrant plantings
  • A peaceful small lake


This is also where you’ll find the picturesque white-sand Oakland Beach. This former amusement park has attractions for everyone’s preferences.


After a fun-filled day at the park and beach, head over to The Barley Beach House for a delicious meal with a stunning view. With its convenient location near Rye Playland Amusement Park, Rye Town Park and Oakland Beach is the perfect spot for a day of fun in the sun.


Rye Nature Center

Birds at a bird feeder at the Rye Nature Center

For a serene escape, visit the Rye Nature Center, a 47-acre forest and wildlife preserve managed by the Friends of Rye Nature Center. Explore the wildlife sanctuary’s ponds, streams, and granite outcroppings by hiking the trails, or join in on events, programs, and camps to learn more about the local flora and fauna.


Marshlands Conservancy

White-tailed deer at the Marshlands Conservancy

Discover the diverse wildlife and habitats of the Marshlands Conservancy, a 147-acre wildlife wonderland with an array of habitats to explore. This is the place to enjoy hiking trails and birdwatching. You’ll see glimpses of magnificent birds, mammals, reptiles, amphibians, and fish that call the conservancy home. This writer typically stumbles upon wild turkeys and white tailed deer here.


Be on the lookout for trails leading onto islands and peninsulas jutting into Long Island Sound.


Edith G. Read Wildlife Sanctuary

A walking trail at the Edith G. Read Wildlife Sanctuary

Birdwatching enthusiasts and nature explorers will love the Edith G. Read Wildlife Sanctuary. This nature lover’s paradise features:

  • A lake
  • Wetland
  • Bamboo grove
  • Fields of native grasses and wildflowers


The sanctuary has been named an important bird area by the National Audubon Society of New York, making it the perfect spot for birdwatching and observing the diverse wildlife inhabiting the area.


Rye Hills Park

Take in the scenic views and enjoy the walking trails and basketball courts at Rye Hills Park, a passive park tucked away behind Crawford Park in Rye Brook, New York. It’s a great spot for a leisurely stroll, a game of basketball, or simply soaking in the natural beauty of the area.


Rye Hills Park offers a tranquil setting to relax and appreciate the area’s beauty.


Rye Golf Club

Hit the greens at the Rye Golf Club, a members-only club with the following amenities:

  • A stunning 18-hole golf course designed by the renowned Devereaux Emmet
  • An indoor golf learning center
  • A golf snack bar
  • A golf shop for all your golfing needs

After a round of golf, cool off with a dip in the sizzling swimming pool or indulge in some fun at the kiddie wading pool and play areas.


Square House Museum at the Rye Historical Society

Square House Museum

While traipsing about the city, do yourself a favor and saunter into the historical landmark that is the Rye Historical Society. Nestled within the Square House Museum, it’s been spinning tales of yesteryears since its inception in 1964.


The Square House Museum, this old dame has had many faces – a homestead, a tavern, a city hall, and now, a museum. It stands tall, with its five period rooms – the front hall, tavern room, warming kitchen, upstairs hallway, and innkeeper’s bedroom – each a silent spectator to the passage of time. Antique furniture, decorative arts, and artifacts whisper tales of tavern life from the late 1700s.


The Society is your ticket to a time machine, a chance to step back into the rich tapestry of Rye’s history. And if you thought the Square House Museum was the only gem in its crown, think again. The Society also operates the Knapp House, the oldest standing structure in Westchester County, dating back to 1667. It houses over 25,000 archived items, each a piece of the puzzle that is the history of the Village of Rye and the Rye Historical Society.


Situated on the Boston Post Road, the Society is your gateway to the past. So, step in and let its collection of artifacts, archives, lectures, programs, and events whisk you away on a journey through time, any time of the year!


Shopping in Rye, NY

Shop till you drop along the main drag of town

If you’re in the mood for some retail therapy, Rye, NY, has got you covered. The town’s only independent bookstore, Arcade Booksellers, offers a wide selection of titles to satisfy your literary cravings.


And for more shopping options, explore the trendy stores in Rye Ridge Shopping Center, Gateway Shopping Center, and along Purchase Street.


Arcade Booksellers

For book lovers, a visit to Arcade Booksellers is an absolute must. This independent bookstore, located in Rye, NY, offers an extensive collection of fiction, non-fiction, and children’s books, ensuring there’s something for everyone.


With a cozy atmosphere and friendly staff, it’s the perfect place to lose yourself in the world of literature and find your next great read.


Restaurants in Rye, NY

Main street in town

Rye, NY, is a food lover’s dream, with a diverse range of dining options to satisfy your cravings. From cozy breakfast spots to upscale seafood bistros and everything in between, Rye has it all.


We’ll take a gastronomic tour of some of the finest eateries in town, featuring Rye Grill & Bar, Rye Roadhouse, Kelly’s Sea Level, Ruby’s Oyster Bar & Bistro, and Longford’s Ice Cream.


Breakfast in Rye, NY

Start your day in Rye, NY, with a delicious breakfast at one of the town’s many eateries. Some options include:


These establishments offer mouthwatering morning meals to energize you for the day ahead.


From pastries and sandwiches to omelets and pancakes, there’s something for every palate.


Rye Grill & Bar

Indulge in American cuisine at Rye Grill & Bar, an elegant restaurant with an exquisite atmosphere and a menu full of delicious dishes. From succulent steaks to fresh seafood, there’s something to please every palate.


For a dining option that caters to the little ones, Rye Grill & Bar is an excellent choice.


Rye Roadhouse

For a taste of Southern comfort, head to Rye Roadhouse, where you’ll find a mouthwatering selection of classic dishes like fried chicken, mac and cheese, and more.


With a laid-back atmosphere and welcoming staff, this is the perfect spot to enjoy a hearty meal with friends and family.


Kelly’s Sea Level

Savor seafood and pub fare at Kelly’s Sea Level, a restaurant in Rye, NY, known for its lip-smackin’ hamburgers and other comfort food delights. Kelly’s Sea Level, with its relaxed ambience in the basement of a residential area home, provides a great setting to unwind and savour some tasty dishes.


Ruby’s Oyster Bar & Bistro

Indulge in exquisite seafood dishes at Ruby’s Oyster Bar & Bistro, a lively restaurant in Rye, NY, that’s sure to tantalize your taste buds. Ruby’s Oyster Bar & Bistro, boasting a menu of fresh oysters, mouth-watering fish, and other tempting seafood delights, is a wonderful spot to relish the tastes of the ocean.


Longford’s Ice Cream

Treat yourself to homemade ice cream at Longford’s Ice Cream, a beloved local shop that churns out 8,000 gallons of creamy goodness every week. Made with only the finest cream, pure cane sugar, imported vanilla, rich cocoas, and other premium ingredients, Longford’s offers over 60 flavors of ice cream, as well as more than 30 flavors of sorbet and gelato.


This is an ideal treat to beat the summer heat in Rye, NY!


Hotels, Inns, and Places to Stay in Rye, NY

Our Greenwich, CT, bed and breakfast is a stone’s throw away from Rye, New York. A mere 10-minute drive, and you’re in a town that’s ripe for exploration. But if you’re planning to stay within the confines of Rye for the weekend, you’ll find the city’s hospitality offerings somewhat sparse.

  • The Courtyard by Marriott Rye, a stalwart in the hotel industry, stands proud in Rye, New York. It’s conveniently situated where the Westchester Cross-County Parkway parts ways with I-95, near the border of Port Chester.


If you’re up for a short drive, here are a couple of charming options:

  • Stanton House Inn, a quaint bed and breakfast nestled in downtown Greenwich, CT, is a 10-minute journey by car from Rye. This historic inn is a unique blend of comfort and hospitality, offering a tranquil retreat from the bustling city life. With its sprawling gardens, cozy common areas, and inviting guest rooms, it’s a home away from home, made even better.
  • Delamar Greenwich Harbor, a waterfront hotel that exudes luxury and elegance in Greenwich, CT. This boutique hotel is known for its refined comfort, personalized service, and unique charm.


Directions to Rye, NY

Reaching Rye, NY, is effortless from Greenwich, CT.


To reach Rye, New York, from New York City, take the I-95 North. Once on the I-95, take exit 20 for Rye, which leads you to Boston Post Road and into the city. The journey typically takes about an hour, depending on traffic.


The Metro-North Railroad’s New Haven Line offers a direct route from New York City to Rye. The journey from Grand Central Station to Rye takes about 45 minutes.


To get to Rye, New York, from Greenwich, Connecticut, and points north, simply take the I-95 South. The journey typically takes about 10 minutes.


You can also take the train to the Rye train station, of course. It’s one of the best train trips from NYC.


More Towns and Cities to Explore Near Rye, NY

If you’re looking to extend your adventure beyond Rye, there are plenty of nearby towns and cities to explore, including:


  • Harrison, New York


  • Rye Brook, NY



  • Greenwich, Connecticut




  • Hartsdale, NY



Each of these places brings its own unique attractions, shopping, dining, and outdoor recreation opportunities, all excellent additions to your Rye, NY, itinerary.



Rye, NY, is a charming seaside town packed with exciting attractions, delicious dining options, and serene natural spaces, all waiting to be explored. From the thrilling rides at Rye Playland Amusement Park to the peaceful trails of the Rye Nature Center, there’s something for everyone in this enchanting destination. So, what are you waiting for? It’s time to embark on your charmed Rye, NY, day trip!


Frequently Asked Questions


Is Rye NY worth visiting?

Rye, NY is worth visiting for its high-end boutiques, galleries, and ‘Restaurant Row’. Its traditional, family-oriented ambiance is sure to please visitors looking for an old-fashioned small town experience.


What is Rye New York famous for?

Rye is famous for its iconic amusement attraction, Rye Playland, and its stunning 60% water-covered waterfront. A waterfront act in 1991 further secured and preserved this breathtaking feature of the city.


Does Rye NY have a downtown?

Rye NY has a quaint downtown shopping district complete with a town square and diverse shopping, restaurants, and other service businesses. Visitors can take advantage of the multiple parking lots owned and operated by the City of Rye.


Should I move to Rye NY?

With its close proximity to the beach and suburban vibe, Rye is a great place to live. With an urban-suburban mix and lots of restaurants, coffee shops, and parks, living in Rye might be the perfect fit for you!


What are the must-visit attractions in Rye, NY?

Take a trip to Rye, NY and experience the delight of the amusement park at Playland, explore the historic Jay Heritage Center, enjoy the beauty of Rye Town Park and Oakland Beach, and browse the books at Rye Free Reading Room.


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